tert-Butyl bromoacetate Property

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)

Safety

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

F 

19

Hazard Note 

Irritant/Flammable/Lachrymatory

TSCA 

T

HazardClass 

3

PackingGroup 

III

HS Code 

29159080

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

tert-Butyl bromoacetate Chemical Properties,Usage,Production

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.]