31191-77-2

Basic information

• Product Name: Cyclopropanecarboxylic acid, 2-bromo-, cis-
• Synonyms: (+/-)-2t-Brom-cyclopropan-r-carbonsaeure;(+/-)-trans-2-Brom-cyclopropancarbonsaeure;trans-2-bromocyclopropanecarboxylic acid;(+/-)-trans-2-bromo-cyclopropanecarboxylic acid
• CAS NO: 31191-77-2
• Molecular Formula: C4H5BrO2
• Molecular Weight: 164.986
• Mol File: 31191-77-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Cyclopropanecarboxylic acid, 2-bromo-, cis-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropanecarboxylic acid, 2-bromo-, cis-(31191-77-2)
• EPA Substance Registry System: Cyclopropanecarboxylic acid, 2-bromo-, cis-(31191-77-2)

Safety Data

• Hazardous Substances Data: 31191-77-2(Hazardous Substances Data)

Upstream product

• 5365-17-3 2,2-dibromocyclopropane-1-carboxylic acid 
• 2867-23-4 opt.-inakt. 2,4-Dibrom-cyclobutanon-⁽¹⁾ 
• 30223-81-5 (+/-)-trans-2-bromo-cyclopropanecarboxylic acid ethyl ester 

Relevant articles and documents

Formal nucleophilic substitution of bromocyclopropanes with amides en route to conformationally constrained β-amino acid derivatives

A chemo- and diastereoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides with secondary amides is described. This method allows for convergent and highly selective synthesis of trans-β-aminocyclopropane carboxylic acid derivatives.

Reactions of 2,2-dibromocyclopropyl carboxylic acids with methyllithium

For reactions of 2,2-dibromocyclopropyl carboxylic acids with methyllithium, the course reaction depends mainly on the position of the carboxyl group.When the COOH group is directly attached to the gem-dibromocyclopropane ring MeLi generally attacks the gem-dibromo moiety and gives the corresponding monobromocyclopropane as the principal product.When the reaction is performed above -80 deg C the monobromides are formed stereospecifically in the trans configuration.The highest yields, as high as 80-90percent, are obtained 0 deg C.When the carboxyl group is not directly attached to the cyclopropane ring most of the MeLi is consumed in an acid-base reaction with the COOH group.