ChemicalBook CAS DataBase List 4-BROMOCROTONIC ACID

4-BROMOCROTONIC ACID synthesis

9synthesis methods

Product Name:4-BROMOCROTONIC ACID
CAS Number:13991-36-1
Molecular formula:C4H5BrO2
Molecular Weight:164.99

4-Bromocrotonic acid is used as a fatty acid blocking agent as an intermediate for the preparation of tetrahydropyridothienopyrimidine derivatives with antiproliferative activity. It can be synthesized by bromination reaction of crotonic acid.

107-93-7
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13991-36-1
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$105.00/250 mg

Yield:13991-36-1 93%

Reaction Conditions:

with N-Bromosuccinimide;dibenzoyl peroxide in tetrachloromethane at 77; for 4 h;

Steps:

6.1.6 (E)-4-Bromobut-2-enoic acid (18)
To a solution of (E)-but-2-enoic acid (10g, 0.116mol) in CCl₄ was added NBS (31g, 0.174mol) and benzoyl peroxide (0.263g, 1.16mmol). Then the mixture reaction was stirred at 77°C for 4h. After the start material was completed, the solvent was removed and n-hexane was added. The precipitate was formed, filtered and dried to obtain desired compound 18 as yellow white solid in 93% yield. ESI-MS m/z 166 [M+H]⁺.

References:

Ji, Xun;Peng, Ting;Zhang, Xu;Li, Jian;Yang, Wei;Tong, Linjiang;Qu, Rong;Jiang, Hualiang;Ding, Jian;Xie, Hua;Liu, Hong [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 7,p. 2366 - 2378]

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