ChemicalBook--->CAS DataBase List--->27466-83-7

27466-83-7

27466-83-7 Structure

27466-83-7 Structure
IdentificationBack Directory
[Name]

4-Bromo-N-methylbenzamide 98%
[CAS]

27466-83-7
[Synonyms]

4-Bromo-N-methylbenzamide
N-Methyl 4-bromobenzamide
N-Methyl-p-bromobenzamide
p-Bromo-N-methylbenzamide
benzamide, 4-bromo-N-methyl-
4-Bromo-N-methylbenzamide 98%
4-bromo-N-methylbenzamide(SALTDATA: FREE)
[Molecular Formula]

C8H8BrNO
[MDL Number]

MFCD00462943
[MOL File]

27466-83-7.mol
[Molecular Weight]

214.07
Chemical PropertiesBack Directory
[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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a
[Hazard Codes ]

Xi
[Risk Statements ]

22
[HazardClass ]

IRRITANT
[HS Code ]

2924297099
Spectrum DetailBack Directory
[Spectrum Detail]

4-Bromo-N-methylbenzamide 98%(27466-83-7)1HNMR
Hazard InformationBack Directory
[Synthesis]

4-Bromobenzoyl chloride

586-75-4

Methylamine

74-89-5

4-Bromo-N-methylbenzamide 98%

27466-83-7

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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