2-BROMO-3-METHYLBENZONITRILE Chemical Properties

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 Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2926907090

2-BROMO-3-METHYLBENZONITRILE Usage And Synthesis

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

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