5-BROMO-2-METHOXYPHENYLACETONITRILE

5-BROMO-2-METHOXYPHENYLACETONITRILE Property

Melting point:

61-63°C

Boiling point:

182.5-183 °C

Density 

1.450±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

White to off-white Solid

Safety

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

RIDADR 

3439

Hazard Note 

Irritant

HazardClass 

IRRITANT, IRRITANT-HARMFUL

HS Code 

2926907090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

5-BROMO-2-METHOXYPHENYLACETONITRILE Chemical Properties,Usage,Production

Uses

2-(5-Bromo-2-methoxyphenyl)acetonitrile is a useful intermediate used in the synthesis of 5-bromo-2-methoxyphenylacetonitrile and some of its derivatives.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 38, p. 2050, 1995 DOI: 10.1021/jm00012a004

Synthesis

GENERAL METHODS: N-bromosuccinimide (NBS, 1.5 eq., 0.3 mmol), catalyst (10 mol%, 0.02 mmol) and acetonitrile (CH3CN, 1.0 mL) were sequentially added to the reaction tube, followed by o-methoxybenzeneacetonitrile (0.2 mmol). The reaction mixture was stirred at room temperature in a dark environment for 12 hours. Upon completion of the reaction, the reaction was quenched by the addition of saturated sodium thiosulfate (Na2S2O3) aqueous solution (2 mL). The reaction mixture was extracted with ethyl acetate (3.5 mL), and the combined organic phases were washed with saturated brine (10 mL), dried over anhydrous sodium sulfate (Na2SO4), and filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure and the residue was purified by fast chromatography on silica gel column with the eluent of petroleum ether/dichloromethane (5:1, v/v) to afford the target product 5-bromo-2-methoxyphenylacetonitrile.

References

[1] Tetrahedron, 2017, vol. 73, # 50, p. 7105 - 7114