2 6-Dimethyl Pyrazine Synthesis Essay

S1. Chemical context top

5,6-Bis(pyridin-2-yl)pyrazine-2,3-di­carb­oxy­lic acid (L1H2) was synthesized to study its coordination behaviour with first row transitions metals (Alfonso, 1999). It exists as a zwitterion, with the adjacent pyridine and pyridinium rings almost coplanar due to the presence of an intra­molecular N—H···N hydrogen bond. The crystal structures of the zwitterion and different charged forms of L1H2, viz. the HCl, HClO4 and HPF6 salts, and details of the hydrogen bonding have been reported (Alfonso et al., 2001).

Metal-catalysed hydrolysis of amino acid esters is a well documented phenomenon (Dugas, 1989). It has been shown previously that the reaction of copper(II) salts with the di­methyl esters of pyrazine-2,3-di­carb­oxy­lic acid (Neels et al., 1997) and 2,5-di­methyl­pyrazine-3,6-di­carb­oxy­lic acid (Wang & Stoeckli-Evans, 1998) resulted in the partial hydrolysis of the ligand and the formation of a two-dimensional network in the first case and a mononuclear complex in the second. Hence, metal-ion-promoted ester hydrolysis leads to the formation of new ligands and becomes an extremely inter­esting manner to prepare new coordination compounds. The title compounds, (I) and (II), were synthesized to study the hydrolysis of these esters with first row transition metals (Alfonso, 1999), and we report herein on their syntheses and crystal structures.

S2. Structural commentary top

As seen in compound (I), Fig.1, the di­methyl ester of L1H2, pyridine ring B (N4/C10–C14) is inclined to the pyrazine ring (A; N1/N2/C1–C4) by 44.8 (2)° and the pyridine and pyrazine N atoms, N1 and N4, are trans to one another. Pyridine ring C (N3/C5–C9) is inclined to pyrazine ring A by 50.3 (2)°. However, here the pyridine and pyrazine N atoms, N2 and N4, are cis to one another. The two pyridine rings, B and C, are inclined to one another by 60.2 (2)° and to the planar pyrazine ring A (r.m.s. deviation 0.032 Å) by 44.8 (2) and 50.3 (2)°, respectively. The acetate groups, O1/O2/C15/C17 and O3/O4/C16/C18, are planar with r.m.s. deviations of 0.027 and 0.007 Å, respectively. They are inclined to the pyrazine ring by 60.3 (3) and 49.8 (3)°, respectively, and to one another by 42.4 (3)°.

Compound (II), the di­ethyl ester of L1H2, possesses twofold rotation symmetry, with the twofold rotation axis bis­ecting the Car—Ciar bonds [ar = aromatic; symmetry code (i): -x + 2, -y + 3/2, z], as shown in Fig. 2. The pyridine N atoms, N2 and N2i, face one another with an N2···N2i separation of 3.043 (3) Å. The two pyridine rings are inclined to one another by 55.1 (1)° and to the pyrazine ring mean plane by 40.7 (1)°, with the pyrazine and pyridine N atoms, N1 and N2, trans to one another. The acetate group, O1/O2/C8/C9 [maximum deviation of 0.012 (3) Å for atom C8] is inclined to the pyrazine ring mean plane by 38.9 (1)°, and by 47.6 (2)° to the acetate group related by the twofold rotation axis. The oxygen atoms, O2 and O2i, are separated by only 2.840 (3) Å. The pyrazine ring in (II) has a slight twist-boat conformation (r.m.s. deviation = 0.046 Å) with the N1/C1/C2 and N1i/C1i/C2i planes inclined to one another by 3.9 (3)°.

As noted above the differences in the structures of the two compounds lies essentially in the orientation of the pyridine rings with respect to the pyrazine ring (cf Figs. 1 and 2). It is possible that the slight distortion of the planarity of the pyrazine ring in (II), mentioned above, is related to the short N2···N2i contact of 3.043 (3) Å of the adjacent pyridine rings and to the even shorter O2···O2i contact of 2.840 (3) Å of the adjacent acetate groups.

S3. Supra­molecular features top

In the crystal of (I), molecules are linked by C—H···N hydrogen bonds, forming chains along [001]; see Table 1 and Fig. 3. The chains are linked via C—H···π inter­actions (Table 1), forming a three-dimensional structure.

In the crystal of (II), molecules are linked via C—H···O hydrogen bonds, forming a three-dimensional framework; see Table 2 and Fig. 4. Within the framework there are a number of C—H···π inter­actions present (Table 2).

S4. Database survey top

\ Besides the structures of the zwitterion and different charged forms of L1H2, viz. the HCl, HClO4 and HPF6 salts (Alfonso et al., 2001), the crystal structures of two copper(II) complexes of L1H2 have been reported, viz: catena-[[[µ3-5,6-bis­(pyridin-2-yl)pyrazine-2,3-di­carboxyl­ate]\ tri­aqua­dibromo­dicopper(II)] methanol solvate trihydrate] and catena-[[[µ4-5,6-bis­(pyridin-2-yl)pyrazine-2,3-di­carboxyl­ate)\ di­aqua­dibromo­dicopper(II) monohydrate] (Neels et al., 2003).

The structure of the isoelectronic compound 3,6-bis­(pyridin-2-yl)pyrazine-2,5-di­carb­oxy­lic acid (L2H2), Fig. 5, has also been reported (Wang & Stoeckli-Evans, 2012a). It too exists as a zwitterion and the structures of its di­hydro­chloride salt and the di­methyl sulfonate disolvate have also been reported (Wang & Stoeckli-Evans, 2012a). The crystal structures of the di­methyl (III) and di­ethyl (IV) esters of L2H2 have been deposited as private communications (Wang & Stoeckli-Evans, 2012b,c) with the Cambridge Structural Database (CSD; Groom & Allen, 2014). Both compounds crystallize in the triclinic space group P1 and possess inversion symmetry. The pyridine rings lie almost in the plane of the pyrazine ring and the N atoms are trans with respect to each other and to the nearest pyrazine N atom (as illustrated in Fig. 5). The ester groups are planar and in both compounds lie almost normal to the pyrazine ring. In the crystals of both compounds, inversion-related molecules are linked via pairs of C—H···O hydrogen bonds, enclosing R22(10) ring motifs, forming chains propagating along [101].

S5. Synthesis and crystallization top

The synthesis of 5,6-bis­(pyridin-2-yl)pyrazine-2,3-di­carb­oxy­lic acid (L1H2) has been reported (Alfonso et al., 2001). The di­methyl and di­ethyl esters, compounds (I) and (II), respectively, were obtained by the usual esterification procedure in acidic medium from the diacid and an excess of the corresponding alcohol.

Synthesis of compound (I): di­methyl-5,6-bis­(pyridin-2-yl)pyrazine-2,3-di­carboxyl­ate L1H2 (1.00 g, 3.11 mmol) was heated under reflux in freshly distilled MeOH (40ml) containing H2SO4 conc. (98%, 1 ml) during 16 h. After stopping the reaction, the temperature of the solution was allowed to cool to room temperature and then poured into an aqueous solution of NaOAc (6 g in 150 ml deionized water). The resulting solution was stirred in an ice bath containing NaCl to afford a white solid which was removed by filtration, washed with cold water and dried under vacuum. Single crystals suitable for X-ray analysis were obtained by the slow diffusion technique from CH2Cl2 and MeOH (yield: 0.77g, 65%; m.p. 410.2–411.7 K). Selected IR bands (KBr pellet, cm-1): ν = 1743(s), 1729(vs), 1339(s), 1302(s), 1283(vs), 1164(s), 1089(vs). 1H NMR (CDCl3, 400 MHz, p.p.m.): δ = 8.34(dt, 2H, J = 4.1Hz, J = 1.0Hz, pyH), 7.99(dt, 2H, J = 7.7Hz, J = 1.0Hz, pyH), 7.82(td, 2H, J = 7.7Hz, J = 1.0Hz, pyH), 7.26(td, 2H, J = 7.7Hz, J = 1.0Hz, pyH), 4.04(s, 6H, CH3). 13C NMR (CDCl3, 50 MHz, p.p.m.): δ = 165.53, 155.98, 153.35, 149.26, 142.92, 137.64, 125.41, 124.49, 54.11. DCI–MS m/z: 351(MH+), 318, 279, 255, 208. Analysis for C18H14N4O4 (350.33), calculated C 61.70, H 4.04, N 15.99 %, found C 61.4, H 3.91, N 15.65 %.

Synthesis of compound (II): di­ethyl-5,6-bis­(pyridin-2-yl)pyrazine-2,3-di­carboxyl­ate

This compound was prepared by the same method as for (I). L1H2 in freshly distilled EtOH containing catalytic amounts of H2SO4 conc. gave compound (II) as a white solid. Slow evaporation of an ethano­lic solution afforded colourless crystals suitable for X-ray analysis (yield: 0.70g, 62%; m.p. 390.5–391.3 K). Selected IR bands (KBr pellet, cm-1): ν = 3055(w), 1737(s), 1723(vs), 1368(s), 1301(s), 1276(vs), 1276(vs), 1161(s), 1086(vs). 1H NMR (CDCl3, 400 MHz, p.p.m.): δ = 8.33(d, 2H, J = 4Hz, pyH), 8.01(d, 2H, J = 7.7Hz, pyH), 7.81(t, 2H, J = 7.7Hz, pyH), 7.24(t, 2H, J = 4.4Hz, pyH), 4.52(m, 4H, J = 7Hz, CH2), 1.45(t, 6H, J = 7.4Hz, CH3). EI–MS m/z: 378 (34), 349 (9), 232 (95), 206 (66), 179 (25), 152 (11), 129 (9), 78(base), 46 (38). Analysis for C20H18N4O4 (378.38), calculated C 63.49, H 4.79, N 14.81 %, found C 63.49, H 4.61, N 14.77 %.

S6. Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 3. For both compounds, the C-bound H-atoms were included in calculated positions and treated as riding atoms: C—H = 0.93–0.98 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms. For compound (I), the Flack parameter (Parsons et al., 2013) is = -0.2 (10), but it has no physical meaning here.

Structure description top

5,6-Bis(pyridin-2-yl)pyrazine-2,3-di­carb­oxy­lic acid (L1H2) was synthesized to study its coordination behaviour with first row transitions metals (Alfonso, 1999). It exists as a zwitterion, with the adjacent pyridine and pyridinium rings almost coplanar due to the presence of an intra­molecular N—H···N hydrogen bond. The crystal structures of the zwitterion and different charged forms of L1H2, viz. the HCl, HClO4 and HPF6 salts, and details of the hydrogen bonding have been reported (Alfonso et al., 2001).

Metal-catalysed hydrolysis of amino acid esters is a well documented phenomenon (Dugas, 1989). It has been shown previously that the reaction of copper(II) salts with the di­methyl esters of pyrazine-2,3-di­carb­oxy­lic acid (Neels et al., 1997) and 2,5-di­methyl­pyrazine-3,6-di­carb­oxy­lic acid (Wang & Stoeckli-Evans, 1998) resulted in the partial hydrolysis of the ligand and the formation of a two-dimensional network in the first case and a mononuclear complex in the second. Hence, metal-ion-promoted ester hydrolysis leads to the formation of new ligands and becomes an extremely inter­esting manner to prepare new coordination compounds. The title compounds, (I) and (II), were synthesized to study the hydrolysis of these esters with first row transition metals (Alfonso, 1999), and we report herein on their syntheses and crystal structures.

As seen in compound (I), Fig.1, the di­methyl ester of L1H2, pyridine ring B (N4/C10–C14) is inclined to the pyrazine ring (A; N1/N2/C1–C4) by 44.8 (2)° and the pyridine and pyrazine N atoms, N1 and N4, are trans to one another. Pyridine ring C (N3/C5–C9) is inclined to pyrazine ring A by 50.3 (2)°. However, here the pyridine and pyrazine N atoms, N2 and N4, are cis to one another. The two pyridine rings, B and C, are inclined to one another by 60.2 (2)° and to the planar pyrazine ring A (r.m.s. deviation 0.032 Å) by 44.8 (2) and 50.3 (2)°, respectively. The acetate groups, O1/O2/C15/C17 and O3/O4/C16/C18, are planar with r.m.s. deviations of 0.027 and 0.007 Å, respectively. They are inclined to the pyrazine ring by 60.3 (3) and 49.8 (3)°, respectively, and to one another by 42.4 (3)°.

Compound (II), the di­ethyl ester of L1H2, possesses twofold rotation symmetry, with the twofold rotation axis bis­ecting the Car—Ciar bonds [ar = aromatic; symmetry code (i): -x + 2, -y + 3/2, z], as shown in Fig. 2. The pyridine N atoms, N2 and N2i, face one another with an N2···N2i separation of 3.043 (3) Å. The two pyridine rings are inclined to one another by 55.1 (1)° and to the pyrazine ring mean plane by 40.7 (1)°, with the pyrazine and pyridine N atoms, N1 and N2, trans to one another. The acetate group, O1/O2/C8/C9 [maximum deviation of 0.012 (3) Å for atom C8] is inclined to the pyrazine ring mean plane by 38.9 (1)°, and by 47.6 (2)° to the acetate group related by the twofold rotation axis. The oxygen atoms, O2 and O2i, are separated by only 2.840 (3) Å. The pyrazine ring in (II) has a slight twist-boat conformation (r.m.s. deviation = 0.046 Å) with the N1/C1/C2 and N1i/C1i/C2i planes inclined to one another by 3.9 (3)°.

As noted above the differences in the structures of the two compounds lies essentially in the orientation of the pyridine rings with respect to the pyrazine ring (cf Figs. 1 and 2). It is possible that the slight distortion of the planarity of the pyrazine ring in (II), mentioned above, is related to the short N2···N2i contact of 3.043 (3) Å of the adjacent pyridine rings and to the even shorter O2···O2i contact of 2.840 (3) Å of the adjacent acetate groups.

In the crystal of (I), molecules are linked by C—H···N hydrogen bonds, forming chains along [001]; see Table 1 and Fig. 3. The chains are linked via C—H···π inter­actions (Table 1), forming a three-dimensional structure.

In the crystal of (II), molecules are linked via C—H···O hydrogen bonds, forming a three-dimensional framework; see Table 2 and Fig. 4. Within the framework there are a number of C—H···π inter­actions present (Table 2).

\ Besides the structures of the zwitterion and different charged forms of L1H2, viz. the HCl, HClO4 and HPF6 salts (Alfonso et al., 2001), the crystal structures of two copper(II) complexes of L1H2 have been reported, viz: catena-[[[µ3-5,6-bis­(pyridin-2-yl)pyrazine-2,3-di­carboxyl­ate]\ tri­aqua­dibromo­dicopper(II)] methanol solvate trihydrate] and catena-[[[µ4-5,6-bis­(pyridin-2-yl)pyrazine-2,3-di­carboxyl­ate)\ di­aqua­dibromo­dicopper(II) monohydrate] (Neels et al., 2003).

The structure of the isoelectronic compound 3,6-bis­(pyridin-2-yl)pyrazine-2,5-di­carb­oxy­lic acid (L2H2), Fig. 5, has also been reported (Wang & Stoeckli-Evans, 2012a). It too exists as a zwitterion and the structures of its di­hydro­chloride salt and the di­methyl sulfonate disolvate have also been reported (Wang & Stoeckli-Evans, 2012a). The crystal structures of the di­methyl (III) and di­ethyl (IV) esters of L2H2 have been deposited as private communications (Wang & Stoeckli-Evans, 2012b,c) with the Cambridge Structural Database (CSD; Groom & Allen, 2014). Both compounds crystallize in the triclinic space group P1 and possess inversion symmetry. The pyridine rings lie almost in the plane of the pyrazine ring and the N atoms are trans with respect to each other and to the nearest pyrazine N atom (as illustrated in Fig. 5). The ester groups are planar and in both compounds lie almost normal to the pyrazine ring. In the crystals of both compounds, inversion-related molecules are linked via pairs of C—H···O hydrogen bonds, enclosing R22(10) ring motifs, forming chains propagating along [101].

Synthesis and crystallization top

The synthesis of 5,6-bis­(pyridin-2-yl)pyrazine-2,3-di­carb­oxy­lic acid (L1H2) has been reported (Alfonso et al., 2001). The di­methyl and di­ethyl esters, compounds (I) and (II), respectively, were obtained by the usual esterification procedure in acidic medium from the diacid and an excess of the corresponding alcohol.

Synthesis of compound (I): di­methyl-5,6-bis­(pyridin-2-yl)pyrazine-2,3-di­carboxyl­ate L1H2 (1.00 g, 3.11 mmol) was heated under reflux in freshly distilled MeOH (40ml) containing H2SO4 conc. (98%, 1 ml) during 16 h. After stopping the reaction, the temperature of the solution was allowed to cool to room temperature and then poured into an aqueous solution of NaOAc (6 g in 150 ml deionized water). The resulting solution was stirred in an ice bath containing NaCl to afford a white solid which was removed by filtration, washed with cold water and dried under vacuum. Single crystals suitable for X-ray analysis were obtained by the slow diffusion technique from CH2Cl2 and MeOH (yield: 0.77g, 65%; m.p. 410.2–411.7 K). Selected IR bands (KBr pellet, cm-1): ν = 1743(s), 1729(vs), 1339(s), 1302(s), 1283(vs), 1164(s), 1089(vs). 1H NMR (CDCl3, 400 MHz, p.p.m.): δ = 8.34(dt, 2H, J = 4.1Hz, J = 1.0Hz, pyH), 7.99(dt, 2H, J = 7.7Hz, J = 1.0Hz, pyH), 7.82(td, 2H, J = 7.7Hz, J = 1.0Hz, pyH), 7.26(td, 2H, J = 7.7Hz, J = 1.0Hz, pyH), 4.04(s, 6H, CH3). 13C NMR (CDCl3, 50 MHz, p.p.m.): δ = 165.53, 155.98, 153.35, 149.26, 142.92, 137.64, 125.41, 124.49, 54.11. DCI–MS m/z: 351(MH+), 318, 279, 255, 208. Analysis for C18H14N4O4 (350.33), calculated C 61.70, H 4.04, N 15.99 %, found C 61.4, H 3.91, N 15.65 %.

Synthesis of compound (II): di­ethyl-5,6-bis­(pyridin-2-yl)pyrazine-2,3-di­carboxyl­ate

This compound was prepared by the same method as for (I). L1H2 in freshly distilled EtOH containing catalytic amounts of H2SO4 conc. gave compound (II) as a white solid. Slow evaporation of an ethano­lic solution afforded colourless crystals suitable for X-ray analysis (yield: 0.70g, 62%; m.p. 390.5–391.3 K). Selected IR bands (KBr pellet, cm-1): ν = 3055(w), 1737(s), 1723(vs), 1368(s), 1301(s), 1276(vs), 1276(vs), 1161(s), 1086(vs). 1H NMR (CDCl3, 400 MHz, p.p.m.): δ = 8.33(d, 2H, J = 4Hz, pyH), 8.01(d, 2H, J = 7.7Hz, pyH), 7.81(t, 2H, J = 7.7Hz, pyH), 7.24(t, 2H, J = 4.4Hz, pyH), 4.52(m, 4H, J = 7Hz, CH2), 1.45(t, 6H, J = 7.4Hz, CH3). EI–MS m/z: 378 (34), 349 (9), 232 (95), 206 (66), 179 (25), 152 (11), 129 (9), 78(base), 46 (38). Analysis for C20H18N4O4 (378.38), calculated C 63.49, H 4.79, N 14.81 %, found C 63.49, H 4.61, N 14.77 %.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 3. For both compounds, the C-bound H-atoms were included in calculated positions and treated as riding atoms: C—H = 0.93–0.98 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms. For compound (I), the Flack parameter (Parsons et al., 2013) is = -0.2 (10), but it has no physical meaning here.

Computing details top

Data collection: STADI4 (Stoe & Cie, 1997) for (I); EXPOSE in IPDS-I (Stoe & Cie, 2004) for (II). Cell refinement: STADI4 (Stoe & Cie, 1997) for (I); CELL in IPDS-I (Stoe & Cie, 2004) for (II). Data reduction: X-RED (Stoe & Cie, 1997) for (I); INTEGRATE in IPDS-I (Stoe & Cie, 2004) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(I) Dimethyl 5,6-bis(pyridin-2-yl)pyrazine-2,3-dicarboxylate top

Crystal datatop
C18H14N4O4F(000) = 728
Mr = 350.33Dx = 1.428 Mg m3
Monoclinic, IaMo Kα radiation, λ = 0.71073 Å
a = 8.4249 (12) ÅCell parameters from 33 reflections
b = 12.2465 (10) Åθ = 14.1–19.6°
c = 16.2561 (13) ŵ = 0.10 mm1
β = 103.730 (8)°T = 293 K
V = 1629.3 (3) Å3Rod, colourless
Z = 40.70 × 0.50 × 0.38 mm
Data collectiontop
Stoe–Siemens AED2
diffractometer
θmax = 25.5°, θmin = 2.1°
ω/\2q scansh = −10→10
3035 measured reflectionsk = 0→14
3028 independent reflectionsl = −19→19
2737 reflections with I > 2σ(I)2 standard reflections every 60 min
Rint = 0.012 intensity decay: 1%
Refinementtop
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.135w = 1/[σ2(Fo2) + (0.0759P)2 + 1.0624P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
3028 reflectionsΔρmax = 0.19 e Å3
238 parametersΔρmin = −0.21 e Å3
2 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0065 (18)
Crystal datatop
C18H14N4O4V = 1629.3 (3) Å3
Mr = 350.33Z = 4
Monoclinic, IaMo Kα radiation
a = 8.4249 (12) ŵ = 0.10 mm1
b = 12.2465 (10) ÅT = 293 K
c = 16.2561 (13) Å0.70 × 0.50 × 0.38 mm
β = 103.730 (8)°
Data collectiontop
Stoe–Siemens AED2
diffractometer
Rint = 0.012
3035 measured reflections2 standard reflections every 60 min
3028 independent reflections intensity decay: 1%
2737 reflections with I > 2σ(I)
Refinementtop
R[F2 > 2σ(F2)] = 0.0502 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.11Δρmax = 0.19 e Å3
3028 reflectionsΔρmin = −0.21 e Å3
238 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)top
xyzUiso*/Ueq
O10.8419 (5)1.1583 (3)0.0691 (2)0.0470 (9)
O21.0295 (4)1.1079 (3)−0.0014 (2)0.0395 (8)
O31.0067 (5)1.1074 (3)0.3016 (2)0.0463 (10)
O41.1454 (4)1.1588 (3)0.2054 (2)0.0355 (8)
N10.9519 (4)0.8948 (3)0.0567 (2)0.0266 (8)
N21.0688 (4)0.8934 (3)0.2330 (2)0.0272 (8)
N31.0738 (4)0.6793 (3)0.3087 (2)0.0279 (8)
N40.8579 (5)0.6232 (3)0.0803 (2)0.0348 (9)
C10.9822 (5)0.8015 (3)0.0992 (2)0.0248 (9)
C20.9784 (5)0.9878 (3)0.1014 (2)0.0259 (9)
C31.0319 (5)0.9857 (3)0.1896 (3)0.0268 (9)
C41.0489 (5)0.8006 (3)0.1880 (2)0.0227 (8)
C51.1158 (5)0.6996 (3)0.2355 (2)0.0248 (9)
C61.2218 (5)0.6347 (4)0.2045 (3)0.0311 (9)
H61.24860.65200.15370.037*
C71.2879 (6)0.5430 (4)0.2500 (3)0.0349 (10)
H71.35950.49790.23030.042*
C81.2459 (6)0.5200 (3)0.3248 (3)0.0345 (10)
H81.28790.45890.35650.041*
C91.1394 (5)0.5903 (4)0.3517 (3)0.0312 (9)
H91.11180.57480.40250.037*
C100.9393 (5)0.6998 (3)0.0486 (2)0.0255 (9)
C110.9763 (6)0.6908 (4)−0.0299 (3)0.0334 (10)
H111.03220.7464−0.04990.040*
C120.9291 (6)0.5984 (4)−0.0777 (3)0.0389 (11)
H120.95430.5900−0.13010.047*
C130.8443 (7)0.5192 (4)−0.0469 (3)0.0413 (12)
H130.80980.4561−0.07790.050*
C140.8113 (7)0.5353 (4)0.0320 (3)0.0439 (13)
H140.75290.48140.05240.053*
C150.9399 (6)1.0942 (4)0.0546 (3)0.0316 (10)
C161.0580 (5)1.0903 (4)0.2399 (3)0.0287 (9)
C171.0131 (8)1.2133 (4)−0.0439 (3)0.0525 (14)
H17A1.09241.2190−0.07740.079*
H17B1.03071.2706−0.00240.079*
H17C0.90531.2199−0.07980.079*
C181.1672 (6)1.2674 (4)0.2412 (3)0.0386 (11)
H18A1.21141.31430.20490.058*
H18B1.24101.26450.29610.058*
H18C1.06361.29550.24640.058*
Atomic displacement parameters (Å2)top
U11U22U33U12U13U23
O10.054 (2)0.0354 (19)0.054 (2)0.0149 (17)0.0183 (17)0.0094 (17)
O20.055 (2)0.0344 (19)0.0313 (17)−0.0011 (15)0.0150 (15)0.0089 (14)
O30.079 (3)0.0309 (19)0.037 (2)−0.0093 (17)0.0314 (19)−0.0065 (14)
O40.0460 (18)0.0266 (17)0.0375 (16)−0.0064 (13)0.0171 (14)−0.0077 (13)
N10.0339 (19)0.0234 (19)0.0235 (18)−0.0009 (14)0.0084 (14)0.0004 (13)
N20.0320 (19)0.027 (2)0.0231 (18)−0.0006 (14)0.0081 (15)−0.0003 (13)
N30.0337 (19)0.0282 (19)0.0223 (18)−0.0009 (15)0.0077 (14)0.0010 (14)
N40.049 (2)0.0326 (19)0.0237 (17)−0.0122 (17)0.0103 (16)−0.0023 (16)
C10.029 (2)0.025 (2)0.023 (2)0.0003 (16)0.0110 (17)0.0009 (16)
C20.027 (2)0.027 (2)0.024 (2)0.0006 (17)0.0066 (16)0.0011 (16)
C30.032 (2)0.023 (2)0.027 (2)0.0005 (17)0.0108 (18)−0.0016 (16)
C40.0233 (19)0.024 (2)0.022 (2)−0.0001 (15)0.0082 (15)0.0013 (15)
C50.029 (2)0.024 (2)0.0201 (19)−0.0017 (16)0.0032 (16)−0.0009 (16)
C60.038 (2)0.029 (2)0.026 (2)0.0039 (19)0.0090 (18)−0.0011 (18)
C70.040 (2)0.027 (2)0.036 (2)0.0047 (19)0.006 (2)−0.0035 (19)
C80.043 (3)0.022 (2)0.034 (2)0.0019 (19)0.0007 (19)0.0013 (18)
C90.038 (2)0.029 (2)0.024 (2)−0.0046 (18)0.0027 (18)0.0040 (18)
C100.031 (2)0.025 (2)0.020 (2)0.0015 (17)0.0040 (16)0.0015 (16)
C110.042 (3)0.034 (2)0.026 (2)−0.0032 (18)0.0130 (18)−0.0015 (18)
C120.053 (3)0.039 (3)0.026 (2)0.001 (2)0.013 (2)−0.007 (2)
C130.059 (3)0.032 (3)0.030 (2)−0.003 (2)0.003 (2)−0.0083 (19)
C140.066 (3)0.031 (2)0.035 (3)−0.018 (2)0.012 (2)0.002 (2)
C150.038 (2)0.030 (2)0.023 (2)−0.002 (2)0.0008 (17)0.0001 (17)
C160.037 (2)0.022 (2)0.025 (2)0.0026 (17)0.0038 (17)−0.0003 (17)
C170.069 (4)0.039 (3)0.045 (3)−0.012 (3)0.005 (3)0.017 (2)
C180.047 (3)0.024 (2)0.046 (3)−0.0043 (19)0.013 (2)−0.006 (2)
Geometric parameters (Å, º)top
O1—C151.202 (6)C6—C71.387 (6)
O2—C151.324 (6)C6—H60.9300
O2—C171.455 (5)C7—C81.373 (7)
O3—C161.200 (6)C7—H70.9300
O4—C161.325 (6)C8—C91.387 (7)
O4—C181.446 (5)C8—H80.9300
N1—C11.329 (5)C9—H90.9300
N1—C21.340 (5)C10—C111.388 (6)
N2—C31.331 (6)C11—C121.377 (7)
N2—C41.341 (5)C11—H110.9300
N3—C91.340 (5)C12—C131.368 (7)
N3—C51.343 (5)C12—H120.9300
N4—C101.335 (6)C13—C141.389 (7)
N4—C141.336 (6)C13—H130.9300
C1—C41.419 (5)C14—H140.9300
C1—C101.489 (6)C17—H17A0.9600
C2—C31.397 (5)C17—H17B0.9600
C2—C151.505 (6)C17—H17C0.9600
C3—C161.508 (6)C18—H18A0.9600
C4—C51.495 (6)C18—H18B0.9600
C5—C61.377 (6)C18—H18C0.9600
C15—O2—C17115.7 (4)N4—C10—C11123.2 (4)
C16—O4—C18116.2 (3)N4—C10—C1117.0 (3)
C1—N1—C2117.5 (3)C11—C10—C1119.7 (4)
C3—N2—C4116.6 (3)C12—C11—C10119.1 (4)
C9—N3—C5116.7 (4)C12—C11—H11120.5
C10—N4—C14116.5 (4)C10—C11—H11120.5
N1—C1—C4121.1 (4)C13—C12—C11118.8 (4)
N1—C1—C10116.2 (3)C13—C12—H12120.6
C4—C1—C10122.7 (4)C11—C12—H12120.6
N1—C2—C3120.9 (4)C12—C13—C14118.3 (4)
N1—C2—C15118.3 (3)C12—C13—H13120.9
C3—C2—C15120.8 (4)C14—C13—H13120.9
N2—C3—C2122.5 (4)N4—C14—C13124.2 (4)
N2—C3—C16116.7 (3)N4—C14—H14117.9
C2—C3—C16120.8 (4)C13—C14—H14117.9
N2—C4—C1121.1 (4)O1—C15—O2125.6 (4)
N2—C4—C5115.8 (3)O1—C15—C2122.9 (4)
C1—C4—C5122.8 (4)O2—C15—C2111.6 (4)
N3—C5—C6123.2 (4)O3—C16—O4126.2 (4)
N3—C5—C4117.7 (3)O3—C16—C3124.5 (4)
C6—C5—C4119.1 (4)O4—C16—C3109.4 (3)
C5—C6—C7119.0 (4)O2—C17—H17A109.5
C5—C6—H6120.5O2—C17—H17B109.5
C7—C6—H6120.5H17A—C17—H17B109.5
C8—C7—C6118.9 (4)O2—C17—H17C109.5
C8—C7—H7120.5H17A—C17—H17C109.5
C6—C7—H7120.5H17B—C17—H17C109.5
C7—C8—C9118.3 (4)O4—C18—H18A109.5
C7—C8—H8120.9O4—C18—H18B109.5
C9—C8—H8120.9H18A—C18—H18B109.5
N3—C9—C8123.9 (4)O4—C18—H18C109.5
N3—C9—H9118.1H18A—C18—H18C109.5
C8—C9—H9118.1H18B—C18—H18C109.5
C2—N1—C1—C4−3.6 (5)C5—N3—C9—C80.1 (6)
C2—N1—C1—C10175.4 (3)C7—C8—C9—N30.4 (7)
C1—N1—C2—C3−1.6 (5)C14—N4—C10—C11−0.4 (7)
C1—N1—C2—C15−178.2 (4)C14—N4—C10—C1176.0 (4)
C4—N2—C3—C2−1.4 (5)N1—C1—C10—N4−133.7 (4)
C4—N2—C3—C16−178.6 (4)C4—C1—C10—N445.3 (5)
N1—C2—C3—N24.3 (6)N1—C1—C10—C1142.8 (5)
C15—C2—C3—N2−179.2 (4)C4—C1—C10—C11−138.2 (4)
N1—C2—C3—C16−178.6 (4)N4—C10—C11—C12−0.7 (7)
C15—C2—C3—C16−2.1 (6)C1—C10—C11—C12−177.0 (4)
Special detailstop

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

 
2,6-dimethyl pyrazine
2,6-dimethylpyrazine
 
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2,6-dimethylpyrazine (Click)
IUPAC Name: 2,6-dimethylpyrazine
Std.InChI: InChI=1S/C6H8N2/c1-5-3-7-4-6(2)8-5/h3-4H,1-2H3
InChI: InChI=1/C6H8N2/c1-5-3-7-4-6(2)8-5/h3-4H,1-2H3
Std.InChIKey: HJFZAYHYIWGLNL-UHFFFAOYSA-N
InChIKey: HJFZAYHYIWGLNL-UHFFFAOYAT
CAS Number: 108-50-9
ECHA EINECS - REACH Pre-Reg: 203-589-4
FDA UNII: N77Q72C9I3
Nikkaji Web: J1.498B
Beilstein Number: 0107052
MDL: MFCD00006148
CoE Number: 2211
XlogP3: 0.50 (est)
Molecular Weight: 108.14376000
Formula: C6 H8 N2
NMR Predictor: Predict (works with chrome or firefox)
EFSA/JECFA Comments: Mixture of positional isomers (2,5- and 2,6-isomers), 2,5- (35-55 %) and 2,6-isomers (45-65 %) (sum 98 %) (EFFA, 2010a).
Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Appearance: white to yellow crystals (est)
Assay: 98.00 to 100.00 % 
Additional Assay Information: sum of 2,3- 2,5- and 2,6- isomers
Food Chemicals Codex Listed: Yes
Melting Point: 37.00 to  48.00 °C. @ 760.00 mm Hg
Boiling Point: 154.00 to  155.00 °C. @ 760.00 mm Hg
Vapor Pressure: 3.873000 mm/Hg @ 25.00 °C. (est)
Flash Point: 127.00 °F. TCC ( 52.78 °C. )
logP (o/w): 0.540
Soluble in:
 alcohol
 essential oils
 water, 3.816e+004 mg/L @ 25 °C (est)
Insoluble in:
 water
Odor Type: chocolate
Odor Strength: high ,
recommend smelling in a 0.10 % solution or less
 cocoa  roasted  nutty  meaty roasted meaty  coffee  
Odor Description:
at 0.10 % in dipropylene glycol. 
cocoa roasted nuts roast beef coffee
 nutty  coffee  cocoa  musty  bready  meaty  
Taste Description:
nutty coffee cocoa musty bready meaty
  
Advanced Biotech
2,6 DIMETHYL PYRAZINE
Odor: Chocolate, Nutty, Roasted
Anhui Haibei
2,6-Dimethyl Pyrazine
Odor: Cocoa roasted nuts roast beef coffee
Anhui Suzhou Jinli Aromatic Chemicals
2,6-Dimethyl Pyrazine
Odor: roast, coffee, peanut, meat
Apiscent Labs
2,6 DIMETHYLPYRAZINE
Odor: Roast, Coffee, Earthnut, Meat
Beijing Lys Chemicals
2,6-Dimethylpyrazine
BOC Sciences
For experimental / research use only.
2,6-Dimethylpyrazine
Charkit Chemical
DIMETHYLPYRAZINE, 2,6- FEMA 3273
EMD Millipore
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2,6-Dimethylpyrazine
Ernesto Ventós
2,6-DIMETHYLPYRAZINE
Odor: ROAST BEEF, COCOA, COFFEE, NUTTY
Excellentia International
2,6-Dimethyl Pyrazine (Pyrazine Mix. # 12, 16, 20) Natural
FCI SAS
2,6-DIMETHYL PYRAZINE
Odor: Roast, coffee, peanut and meat
Frutarom
2,6-DIMETHYLPYRAZINE
≥99.00%, NI, Kosher
Odor: Cocoa, Coffee, Meaty, Nutty, Roast
Use: Suggested Uses: Bakery, Chocolate, Cocoa, Coffee, Nut, Savoury, Tobacco
Indukern F&F
2,6-DIMETHYL PYRAZINE
CROP CALENDAR
Jiangyin Healthway
2,6-Dimethyl Pyrazine
New functional food ingredients
Jinan Enlighten Chemical Technology(Wutong Aroma )
2,6-Dimethyl pyrazine, Kosherk
M&U International
2,6-DIMETHYL PYRAZINE, Kosher
Matrix Scientific
For experimental / research use only.
2,6-Dimethylpyrazine, 95+%
Moellhausen
2,6-DIMETHYL PYRAZINE
Odor: coffee, nut, cocoa, aromatic
Pearlchem Corporation
2,6-Dimethyl Pyrazine
Penta International
2,6-DIMETHYL PYRAZINE, Kosher
Pyrazine Specialties
2,6-Dimethylpyrazine
Reincke & Fichtner
2,6-Dimethylpyrazine
Riverside Aromatics
2,6-Dimethylpyrazine
Robinson Brothers
2,6-Dimethyl pyrazine F&F
https://www.robinsonbrothers.uk/chemistry-competences
Santa Cruz Biotechnology
For experimental / research use only.
2,6-Dimethylpyrazine
Sigma-Aldrich
2,6-Dimethylpyrazine, ≥98%, FG
Odor: meaty; nutty; coffee.
Certified Food Grade Products
Sunaux International
2,6-Dimethyl Pyrazine
Taytonn
2,6-Dimethylpyrazine
Odor: Cocoa, Coffee, Meaty, Nutty, Roast
TCI AMERICA
For experimental / research use only.
2,6-Dimethylpyrazine >98.0%(GC)(T)
Tengzhou Jitian Aroma Chemiclal
2,6-Dimethyl Pyrazine
Tengzhou Xiang Yuan Aroma Chemicals
2,6-Dimethyl Pyrazine
Treatt
2,6-Dimethylpyrazine
Vigon International
Dimethyl-2,6 Pyrazine
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 10 - Flammable.
R 22 - Harmful if swallowed.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50  880 mg/kg
Drug and Chemical Toxicology. Vol. 3, Pg. 249, 1980.

intraperitoneal-mouse LD50  1080 mg/kg
Toxicology and Applied Pharmacology. Vol. 17, Pg. 244, 1970.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for 2,6-dimethyl pyrazine usage levels up to:
  0.0500 % in the fragrance concentrate.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 1.30 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 2.00 (μg/capita/day)
Structure Class: II
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 5
Click here to view publication 5
 average usual ppmaverage maximum ppm
baked goods: -10.00000
beverages(nonalcoholic): -10.00000
beverages(alcoholic): --
breakfast cereal: -10.00000
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -10.00000
fruit ices: -10.00000
gelatins / puddings: -10.00000
granulated sugar: --
gravies: -10.00000
hard candy: -10.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: -10.00000
milk products: -10.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: -10.00000
sugar substitutes: --
sweet sauces: --
Flavor & Extract Manufacturers Association (FEMA) reference(s):
The FEMA GRAS assessment of pyrazine derivatives used as flavor ingredients.View pdf
European Food Safety Athority(efsa): Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
European Food Safety Authority (EFSA) reference(s):
Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request from the Commission related to Flavouring Group Evaluation 17 (FGE.17): Pyrazine derivatives from chemical group 24 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf
Flavouring Group Evaluation 50 (FGE.50): Consideration of pyrazine derivatives evaluated by JECFA (57th meeting) structurally related to pyrazine derivatives evaluated by EFSA in FGE.17 (2005) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf
Flavouring Group Evaluation 17, Revision 1 (FGE.17Rev1): Pyrazine derivatives from chemical group 24 - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) [1]
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 17, Revision 2 (FGE.17Rev2): Pyrazine derivatives from chemical group 24
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 50, Revision 1 (FGE.50Rev1): Consideration of pyrazine derivatives evaluated by JECFA (57th meeting) structurally related to pyrazine derivatives evaluated by EFSA in FGE.17Rev2 (2010)
View page or View pdf
Safety and efficacy of pyrazine derivatives including saturated ones belonging to chemical group 24 when used as flavourings for all animal species
View page or View pdf
EPI System: View
Chemical Carcinogenesis Research Information System: Search
Env. Mutagen Info. Center: Search
EPA Substance Registry Services (TSCA): 108-50-9
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 7938
National Institute of Allergy and Infectious Diseases: Data
WISER: UN 1325
WGK Germany: 3
 2,6-dimethylpyrazine
Chemidplus: 0000108509
RTECS: UQ2975000 for cas# 108-50-9
Potential Blenders and core components note

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