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tert-Butyl bromoacetate

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tert-Butyl bromoacetate Basic information

Product Name:
tert-Butyl bromoacetate
Synonyms:
  • T-BUTYL BROMOACETATE
  • 1,1-Dimethylethyl 2-bromoacetate
  • 1,1-Dimethylethyl bromoacetate
  • bromoacetic acid T-butyl ester
  • tertiary butyl bromoacetate
  • 2-Bromoacetic acid-t-butylester
  • #ntert.-Butyl bromoacetate
  • tert-Butylbromoacetate,98%
CAS:
5292-43-3
MF:
C6H11BrO2
MW:
195.05
EINECS:
226-133-6
Product Categories:
  • Pharmaceutical intermediates
  • organic chemical
  • Building Blocks
  • C6 to C7
  • Carbonyl Compounds
  • Chemical Synthesis
  • ACID BASED BROMO COMPOUNDS
  • C6 to C7
  • Carbonyl Compounds
  • Esters
  • Organic Building Blocks
  • K00001
Mol File:
5292-43-3.mol
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tert-Butyl bromoacetate Chemical Properties

Melting point:
44-47 °C
Boiling point:
50 °C10 mm Hg(lit.)
Density 
1.338
vapor pressure 
1.62hPa at 25℃
refractive index 
n20/D 1.445(lit.)
Flash point:
121 °F
storage temp. 
0-6°C
solubility 
Chloroform, Ethyl Acetate (Slightly)
form 
Liquid
Specific Gravity
1.333 (20/4℃)
color 
Clear colorless to yellow
Water Solubility 
Miscible with ethanol, chloroform and ethyl acetate. Immiscible with water.
Sensitive 
Lachrymatory
BRN 
1753010
InChIKey
BNWCETAHAJSBFG-UHFFFAOYSA-N
CAS DataBase Reference
5292-43-3(CAS DataBase Reference)
NIST Chemistry Reference
Acetic acid, bromo-, 1,1-dimethylethyl ester(5292-43-3)
EPA Substance Registry System
Acetic acid, bromo-, 1,1-dimethylethyl ester (5292-43-3)
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Safety Information

Hazard Codes 
Xi,F
Risk Statements 
10-36/37/38
Safety Statements 
26-24/25-16
RIDADR 
UN 1993 3/PG 3
WGK Germany 
3
19
Hazard Note 
Irritant/Flammable/Lachrymatory
TSCA 
T
HazardClass 
3
PackingGroup 
III
HS Code 
29159080

MSDS

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tert-Butyl bromoacetate Usage And Synthesis

Chemical Properties

clear colorless to yellow liquid

Uses

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.

Uses

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.

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.]

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