4-Bromo-N-methylbenzamide 98% Chemical Properties

Melting point:

173-174℃

Boiling point:

329.8±25.0 °C(Predicted)

Density 

1.67 g/cm3

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

14.63±0.46(Predicted)

color 

White to off-white

CAS DataBase Reference

27466-83-7

Safety Information

Hazard Codes 

Xi

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2924297099

4-Bromo-N-methylbenzamide 98% Usage And Synthesis

Synthesis

The general procedure for the synthesis of N-methyl-4-bromobenzamide from 4-bromobenzoyl chloride and monomethylamine was as follows: 4-bromobenzoyl chloride (5.0 g, 22.8 mmol) was dissolved in dichloromethane (DCM, 100 mL), followed by the addition of triethylamine (TEA, 7.0 mL, 50.2 mmol). A THF solution of methylamine (20 mL, 2.0 N) was added slowly and dropwise with stirring. The reaction mixture was stirred for 1 h at room temperature and then the reaction was quenched with 2.0 N hydrochloric acid (50 mL). The reaction mixture was extracted with dichloromethane (2 x 100 mL) and the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the white solid product N-methyl-4-bromobenzamide (4.8 g, 98% yield). The product was confirmed by NMR hydrogen spectrum (299.954 MHz, CDCl3): δ 7.62 (d, 2H), 7.55 (d, 2H), 6.16 (s, 3H), 3.00 (d, 6H); mass spectrum (m/z): 215.

References

[1] Patent: WO2006/64251, 2006, A1. Location in patent: Page/Page column 60-61
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 11, p. 4860 - 4882
[3] Tetrahedron, 1973, vol. 29, p. 1073 - 1081
[4] Patent: US5654299, 1997, A
[5] Tetrahedron Letters, 2008, vol. 49, # 11, p. 1725 - 1728

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