tert-Butyl bromoacetate

Chemical properties

clear colorless to yellow liquid

The Uses of tert-Butyl bromoacetate

tert-Butyl Bromoacetate is a halogenated t-butyl acetate commonly used as an alkylating agent. tert-Butyl Bromoacetate is used in the synthesis of collagenase inhibitors.

The Uses of tert-Butyl bromoacetate

tert-Butyl bromoacetate is used as an intermediate in the production of dyes, pharmaceuticals, agrochemicals and in organic compounds. It finds application as an alkylating agent. It plays an important role to prepare (2-oxo-4-vinyl-azetidin-1-yl)-acetic acid tert-butyl ester and in collagenase inhibitors synthesis.

What are the applications of Application

tert-Butyl bromoacetate is a common alkylating agent

What are the applications of Application

tert-Butyl bromoacetate has been used in the synthesis of:
nitrilotriacetic acid end-functionalized polystyrene by atom transfer radical polymerization
building block for substituted t-butyl acetates
dihydropyranyl prelinker which is useful in polymer-assisted deprotection of oligosacchararides
collagenase inhibitor (S,S,R)-(-)-actinonin It is the starting reagent for the synthesis of N-Oxalylglycine derivatives.

Preparation

Tert-butyl bromoacetate ester was synthesized using bromoacetic acid and isobutylene as raw materials,Amberlyst 15,a strong acidic cation exchange resin,as catalyst,and tert-butanol as modifier.

General Description

tert-Butyl bromoacetate serves as building blocks during the synthesis of model N-substituted oligoglycines (peptoids) containing an N-linked lactoside side-chain.

Flammability and Explosibility

Flammable

Safety

Tert-Butyl bromoacetate is a lachrymator. The reagent, reaction and its work-up should be handled in an adequately ventilated fume hood while wearing gloves, safety glasses and laboratory coat.

Purification Methods

Dissolve the ester in Et2O, wash it well with ice cold 10% aqueous K2CO3, dry it over CaCl2, filter and evaporate the Et2O, then fractionate it through a Vigreux column (p 11) in a vacuum. LACHRYMATORY. [Abramovitch et al. J Am Chem Soc 64 2274 1942, Abramovitch & Hauser J Am Chem Soc 65 986 1943, Beilstein 2 III 482.]