METHYL PYRAZINE-2-CARBOXYLATE Chemical Properties

Melting point:

57-61 °C(lit.)

Boiling point:

104°C/7mmHg(lit.)

Density 

1.213±0.06 g/cm3(Predicted)

Flash point:

>100°(212°F)

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

pka

-0.91±0.10(Predicted)

color 

Clear colorless

Merck 

14,7959

BRN 

118345

InChI

InChI=1S/C6H6N2O2/c1-10-6(9)5-4-7-2-3-8-5/h2-4H,1H3

InChIKey

TWIIRMSFZNYMQE-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=CN=C1

LogP

-0.230

CAS DataBase Reference

6164-79-0(CAS DataBase Reference)

EPA Substance Registry System

Pyrazinecarboxylic acid, methyl ester (6164-79-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

METHYL PYRAZINE-2-CARBOXYLATE Usage And Synthesis

Chemical Properties

White solid

Synthesis

To a solution of 2-pyrazinecarboxylic acid (5.80 g, 46.5 mmol) in dichloromethane (100 mL) was slowly added oxalyl chloride (5.10 mL, 60.4 mmol), followed by the addition of a catalytic amount of DMF.The reaction mixture was stirred for 6 hr. at 23° C. The reaction was completed with the addition of methanol (30 mL). After completion of the reaction, methanol (30 mL) was added slowly and stirring was continued for 30 min. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (200 mL) and washed sequentially with saturated aqueous sodium bicarbonate (1 x 100 mL) and brine (1 x 100 mL). The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford 3.38 g (53% yield) of the crude methyl pyrazine-2-carboxylate, which could be used in the next step of the reaction without further purification.1H NMR (400 MHz, CDCl3): δ 9.34 (d, 1H), 8.79 (d, 1H), 8.74 (dd, 1H), 4.06 (s 3H); LCMS (Method A): tR = 0.48 min, m/z 139.3 (M + H)+.

References

[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 12, p. 2843 - 2851
[2] Journal of the American Chemical Society, 1990, vol. 112, # 17, p. 6248 - 6254
[3] Patent: WO2004/48369, 2004, A1. Location in patent: Page 8
[4] Tetrahedron Letters, 2009, vol. 50, # 28, p. 4030 - 4032
[5] Patent: WO2016/207914, 2016, A2. Location in patent: Page/Page column 3; 13; 14

METHYL PYRAZINE-2-CARBOXYLATE(6164-79-0)Related Product Information

• METHYL 3-AMINO-5,6-DICHLORO-2-PYRAZINECARBOXYLATE
• METHYL PYRAZINE-2-CARBOXYLATE
• Methyl 3-amino-2-pyrazinecarboxylate
• 2,3-Pyrazinecarboxylic anhydride
• ETHYL 2-QUINOXALINECARBOXYLATE
• Furo[2,3-b]pyrazine-6-carboxylic acid, 7-amino-, ethyl ester (9CI)
• Methyl 5-chloropyrazine-2-carboxylate
• METHYL 5-BROMOPYRAZINE-2-CARBOXYLATE
• 3-AMINO-6-IODOPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER
• 5-Hydroxypyrazine-2-carboxylic acid methyl ester
• METHYL-2-METHYL-PYRAZINE-5-CARBOXYLATE
• Pyrazinecarboxylic acid, 6-amino-, methyl ester (9CI)
• Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate
• Methyl 3-Amino-6-Bromopyrazine-2-Carboxylic Ester
• 2-Pyrazinecarboxylic acid
• 2-(ETHOXYCARBONYL)-3-METHYLQUINOXALINEDIIUM-1,4-DIOLATE
• 2-(METHOXYCARBONYL)-3-METHYLQUINOXALINEDIIUM-1,4-DIOLATE
• methyl 3-Chloro-5-methyl-pyrazine-2-carboxylate