tert-Butyl bromoacetate

tert-Butyl bromoacetate
  • CAS No.:5292-43-3
Other grades of this product :
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
Mol File:5292-43-3.mol
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.)
Fp 121 °F
storage temp. 0-6°C
form Liquid
Specific Gravity1.333 (20/4℃)
color Clear colorless to yellow
Water Solubility Miscible with ethanol, chloroform and ethyl acetate. Immiscible with water.
Sensitive Lachrymatory
BRN 1753010
InChIKeyBNWCETAHAJSBFG-UHFFFAOYSA-N
CAS DataBase Reference5292-43-3(CAS DataBase Reference)
NIST Chemistry ReferenceAcetic acid, bromo-, 1,1-dimethylethyl ester(5292-43-3)
EPA Substance Registry SystemAcetic acid, bromo-, 1,1-dimethylethyl ester (5292-43-3)
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 Information
ProviderLanguage
t-Butyl 2-bromo acetate English
SigmaAldrich English
ACROS English
ALFA English
tert-Butyl bromoacetate Usage And Synthesis
Chemical Propertiesclear colorless to yellow liquid
Usestert-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.
Usestert-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.
Applicationtert-Butyl bromoacetate has been used in the synthesis of:nitrilotriacetic acid end-functionalized polystyrene by atom transfer radical polymerizationbuilding block for substituted t-butyl acetatesdihydropyranyl prelinker which is useful in polymer-assisted deprotection of oligosacchararidescollagenase inhibitor (S,S,R)-(-)-actinonin It is the starting reagent for the synthesis of N-Oxalylglycine derivatives.
PreparationTert-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 Descriptiontert-Butyl bromoacetate serves as building blocks during the synthesis of model N-substituted oligoglycines (peptoids) containing an N-linked lactoside side-chain.
Flammability and ExplosibilityFlammable
Purification MethodsDissolve 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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