2-BROMO-3-METHYLBENZONITRILE

2-BROMO-3-METHYLBENZONITRILE Property

Melting point:

67-71 °C

Boiling point:

286.8±28.0 °C(Predicted)

Density 

1.51±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder

Appearance

White to off-white Solid

Safety

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2926907090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

2-BROMO-3-METHYLBENZONITRILE Chemical Properties,Usage,Production

Synthesis

Step 2: To a solution of 2-bromo-3-methylbenzamide (12 g, 56.1 mmol) in N,N-dimethylformamide (DMF, 100 mL) was slowly added a solution of cyanuric chloride (15.47 g, 84.1 mmol) in DMF (50 mL) at 0 °C and under nitrogen protection. After addition, the reaction mixture was brought to room temperature and stirred overnight. Thin layer chromatography (TLC, unfolding agent: petroleum ether/ethyl acetate = 1:1) was monitored to show complete reaction. The reaction mixture was poured into water (500 mL) and extracted with ethyl acetate (EtOAc, 200 mL x 2). The organic phases were combined and washed sequentially with saturated aqueous sodium carbonate (200 mL × 2), saturated saline (200 mL × 4), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2-bromo-3-methylbenzonitrile (11 g, 100% yield) as an off-white solid.1H NMR (400 MHz, CDCl3): δ 7.51-7.45 (m, 2H), 7.33 -7.29 (m, 1H), 2.47 (s, 3H).

References

[1] Patent: WO2013/132376, 2013, A1. Location in patent: Page/Page column 226
[2] Organic Letters, 2018, vol. 20, # 3, p. 728 - 731
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 2, p. 644 - 651
[4] Patent: WO2011/22337, 2011, A1. Location in patent: Page/Page column 73-74