methyl 3-bromopyrazine-2-carboxylate Chemical Properties

Melting point:

44℃

Boiling point:

264.7±35.0℃ (760 Torr)

Density 

1.669±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

113.9±25.9℃

storage temp. 

2-8°C

form 

solid

pka

-2.41±0.10(Predicted)

color 

Off-white to grey

InChI

InChI=1S/C6H5BrN2O2/c1-11-6(10)4-5(7)9-3-2-8-4/h2-3H,1H3

InChIKey

CMITUAXQMWSHLL-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=NC=CN=C1Br

Safety Information

HS Code 

2933998090

methyl 3-bromopyrazine-2-carboxylate Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl methyl 3-bromopyrazine-2-carboxylate from methyl 3-aminopyrazine-2-carboxylate: bromine (3.91 g, 24.46 mmol) was added slowly and dropwise at 0 °C to a stirred mixture containing methyl 3-aminopyrazine-2-carboxylate (1.27 g, 8.29 mmol) and hydrobromic acid (4.70 mL, 41.5 mmol). . Subsequently, a solution of sodium nitrite (1.44 g, 20.9 mmol) dissolved in water (6 mL) was added dropwise. The reaction mixture was continued to be stirred at 0 °C for 15 min. Upon completion of the reaction, the pH was adjusted to 8 with saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate (80 mL) and chloroform (50 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to afford 1.13 g (63% yield) of an orange oil, which solidified to the target product, methyl methyl-3-bromopyrazine-2-carboxylate, upon standing.

References

[1] Patent: WO2006/91506, 2006, A2. Location in patent: Page/Page column 47
[2] Patent: WO2006/49681, 2006, A2. Location in patent: Page/Page column 45-46
[3] Patent: WO2006/121588, 2006, A2. Location in patent: Page/Page column 51
[4] Patent: WO2006/121860, 2006, A2. Location in patent: Page/Page column 51
[5] Patent: WO2006/121904, 2006, A1. Location in patent: Page/Page column 51

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