2-(3-bromopyridin-2-yl)acetonitrile

2-(3-bromopyridin-2-yl)acetonitrile Property

Melting point:

63-64 °C(Solv: ethyl ether (60-29-7))

Boiling point:

279.5±25.0 °C(Predicted)

Density 

1.575±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

0.82±0.22(Predicted)

Appearance

White to yellow Solid

Safety

HS Code 

2933399990

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

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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.

2-(3-bromopyridin-2-yl)acetonitrile Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 3-bromo-2-pyridineacetonitrile from 2,3-dibromopyridine and acetonitrile: A tetrahydrofuran (THF, 8 mL) solution of acetonitrile (87 mg, 2.13 mmol) was slowly added to a THF solution of n-butyllithium (n-BuLi, 1.78 mL, 4.26 mmol) at -78 °C and stirred for 1 hour at -78 °C. Subsequently, a THF (2 mL) solution of 2,3-dibromopyridine (500 mg, 2.13 mmol) was slowly added at the same temperature. The reaction mixture was continued to be stirred at -78 °C for 1.5 h and then slowly warmed up to room temperature. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride (NH4Cl) solution and the organic phase was extracted with ethyl acetate (EA, 100 mL x 3). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (HPLC) with the mobile phase of acetonitrile/water (containing 10 nM ammonium bicarbonate, NH4HCO3) to afford the target product 3-bromo-2-pyridineacetonitrile (110 mg, 22% yield) as a white solid. Liquid chromatography-mass spectrometry (LCMS) analysis showed [MH]+ = 197.

References

[1] Synlett, 2000, # 10, p. 1488 - 1490
[2] Patent: WO2017/221092, 2017, A1. Location in patent: Paragraph 00161
[3] Patent: US2012/277247, 2012, A1. Location in patent: Page/Page column 12