N-benzyl-2-broMo-2-MethylpropanaMide

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N-benzyl-2-broMo-2-MethylpropanaMide Basic information
Product Name:N-benzyl-2-broMo-2-MethylpropanaMide
Synonyms:N-benzyl-2-broMo-2-MethylpropanaMide;Propanamide, 2-bromo-2-methyl-N-(phenylmethyl)-
CAS:60110-37-4
MF:C11H14BrNO
MW:256.14
EINECS:
Product Categories:
Mol File:60110-37-4.mol
N-benzyl-2-broMo-2-MethylpropanaMide Structure
N-benzyl-2-broMo-2-MethylpropanaMide Chemical Properties
Melting point 71-72 °C(Solv: ligroine (8032-32-4))
Boiling point 383.3±35.0 °C(Predicted)
density 1.341±0.06 g/cm3(Predicted)
storage temp. 2-8°C
pka14.94±0.46(Predicted)
AppearanceWhite to light yellow Solid
Safety Information
MSDS Information
N-benzyl-2-broMo-2-MethylpropanaMide Usage And Synthesis
Synthesis
2-Bromoisobutyryl Bromide

20769-85-1

Benzylamine

100-46-9

N-benzyl-2-broMo-2-MethylpropanaMide

60110-37-4

2-Bromoisobutyryl bromide was slowly added dropwise to a solution of dichloromethane (CH2Cl2, 0.25 M) containing benzylamine and triethylamine (TEA) at 0 °C. The reaction mixture was kept at this temperature and stirred until complete consumption of the feedstock was confirmed by TLC analysis (unfolding agent ratio of 3:1 hexane/ethyl acetate). Subsequently, the reaction mixture was gradually warmed to room temperature and the reaction was quenched with deionized water. The organic phase was separated and washed three times with deionized water. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The product was further purified by hexane/ethyl acetate mixed solvent recrystallization or silica gel column chromatography (eluent ratio 3:1 hexane/ethyl acetate) to afford N-benzyl-2-bromo-2-methylpropionamide in 45-90% yield as a colorless solid.

References[1] Journal of the American Chemical Society, 2011, vol. 133, # 20, p. 7688 - 7691
[2] Patent: US2012/271046, 2012, A1. Location in patent: Page/Page column 6-7
[3] RSC Advances, 2015, vol. 5, # 93, p. 76401 - 76418
[4] Chemische Berichte, 1898, vol. 31, p. 3237
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, p. 767 - 771
N-benzyl-2-broMo-2-MethylpropanaMide Preparation Products And Raw materials
Raw materials2-Bromoisobutyryl Bromide-->Benzylamine-->Dichloromethane-->Triethylamine
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