5-BroMo-3-Methylpyrazin-2-ol

5-BroMo-3-Methylpyrazin-2-ol Property

Density 

1.84±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

10.05±0.60(Predicted)

Appearance

Light yellow to yellow Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

5-BroMo-3-Methylpyrazin-2-ol Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 2-hydroxy-3-methyl-5-bromopyrazine from 2-hydroxy-3-methylpyrazine was as follows: to a solution of 3-methylpyrazin-2-ol (1.5 g, 13.62 mmol) in anhydrous N,N-dimethylformamide (DMF, 20 mL) was added batchwise at 0 °C N-bromosuccinimide (NBS, 2.67 g, 14.98 mmol). The reaction mixture was slowly warmed to room temperature and stirred overnight. Upon completion of the reaction, the mixture was poured into ice water and extracted with a solvent mixture of isopropanol (IPA)/dichloromethane (DCM, 1/5, v/v). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with 80% ethyl acetate/hexane (v/v) as eluent to afford 2-hydroxy-3-methyl-5-bromopyrazine as white solid (1.97 g, 10.42 mmol, 77% yield). The product was analyzed by mass spectrometry (LCMS) with measured m/z = 189.0 [M+H]+ (calculated exact mass of C5H5BrN2O: 188.0).1H NMR (400 MHz, DMSO-d6) δppm: 2.27 (d, J = 0.5 Hz, 3H), 7.73 (s, 1H), 12.3 (s, 1H).

References

[1] Patent: WO2011/127051, 2011, A1. Location in patent: Page/Page column 205