89123-64-8

Basic information

• Product Name: 2-bromocyclopropanecarboxylic acid
• CAS NO: 89123-64-8
• Molecular Formula: C₄H₅BrO₂
• Molecular Weight: 164.9853
• Mol File: 89123-64-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 265.1°C at 760 mmHg
• Flash Point: 114.1°C
• Density: 2.066g/cm³
• Vapor Pressure: 0.00272mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: 2-bromocyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromocyclopropanecarboxylic acid(89123-64-8)
• EPA Substance Registry System: 2-bromocyclopropanecarboxylic acid(89123-64-8)

Safety Data

• Hazardous Substances Data: 89123-64-8(Hazardous Substances Data)

Synthetic route

cyclopropane-1,1-dicarboxylic acid (598-10-7) → 2-bromo-cyclopropanecarboxylic acid (89123-64-8)

Conditions	Yield
With chloroform durch Bromierung im ultravioletten Licht und anschliessend Destillation unter 20 mm Druck;

Upstream product

• 30223-81-5 (+/-)-trans-2-bromo-cyclopropanecarboxylic acid ethyl ester 
• 5365-17-3 2,2-dibromocyclopropane-1-carboxylic acid 
• 598-10-7 cyclopropane-1,1-dicarboxylic acid 
• 2867-23-4 opt.-inakt. 2,4-Dibrom-cyclobutanon-⁽¹⁾ 

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.