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

pka

14.94±0.46(Predicted)

Appearance

White to light yellow Solid

N-benzyl-2-broMo-2-MethylpropanaMide Usage And Synthesis

Synthesis

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

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