2-Pyrazinylmethanol Chemical Properties

Melting point:

38.5

Boiling point:

60°C/0.2mmHg(lit.)

Density 

1.227±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

powder to lump

pka

13.48±0.10(Predicted)

color 

White to Light yellow

λmax

265nm(EtOH)(lit.)

LogP

-0.181 (est)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-37/38-22

Safety Statements 

26-36/37/39-24/25-39

RTECS 

UQ3625000

Hazard Note 

Irritant

HS Code 

2933998090

2-Pyrazinylmethanol Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-hydroxymethylpyrazine from methyl pyrazine-2-carboxylate was as follows: methyl pyrazine-2-carboxylate (8.5 g) was dissolved in water (200 mL), sodium borohydride (11.65 g) was added, and the reaction mixture was stirred. A vigorous exothermic phenomenon was observed during the addition. After continuing to stir vigorously for 30 minutes, ethanol (80 mL) and saturated potassium carbonate solution (150 mL) were added sequentially. The mixture was continued to be stirred for 30 minutes and subsequently extracted with ethyl acetate (5 x 150 mL) and dichloromethane (5 x 150 mL). The organic phases were combined, dried and concentrated to give pyrazin-2-ylmethanol as a yellow oil (5.43 g, 80% yield), which could be used in the next reaction without further purification. The NMR hydrogen spectrum (DMSO-D6) data of the product were as follows: δ 4.65 (s, 2H), 5.57 (br s, 1H), 8.54 (d, 2H), 8.71 (s, 1H).

References

[1] Journal of Organic Chemistry, 2018, vol. 83, # 3, p. 1431 - 1440
[2] Patent: WO2004/93880, 2004, A1. Location in patent: Page/Page column 86
[3] Patent: WO2017/214359, 2017, A1. Location in patent: Page/Page column 73
[4] Synthetic Communications, 2005, vol. 35, # 24, p. 3187 - 3190
[5] Patent: US2011/237584, 2011, A1. Location in patent: Page/Page column 132

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