Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

124230

Sigma-Aldrich

tert-Butyl bromoacetate

98%

Synonym(s):

Bromoacetic acid tert-butyl ester, t-Butyl bromoacetate, tert-Butyl 2-bromoacetate

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Linear Formula:
BrCH2COOC(CH3)3
CAS Number:
5292-43-3
Molecular Weight:
195.05
Beilstein:
1753010
EC Number:
226-133-6
MDL number:
MFCD00000188
UNSPSC Code:
12352100
PubChem Substance ID:
24847606
NACRES:
NA.22

Quality Level

200

Assay

98%

form

liquid

refractive index

n20/D 1.445 (lit.)

bp

50 °C/10 mmHg (lit.)

density

1.321 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)OC(=O)CBr

InChI

1S/C6H11BrO2/c1-6(2,3)9-5(8)4-7/h4H2,1-3H3

InChI key

BNWCETAHAJSBFG-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

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.

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.

Signal Word

Danger

Hazard Statements

H226,H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

120.2 °F - closed cup

Flash Point(C)

49 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

SYNTHESIS OF (NITRILOTRIACETIC ACID)-END-FUNCTIONALIZED POLYSTYRENE USING ATOM TRANSFER RADICAL POLYMERIZATION.
Cho HY, et al.
Synthesis, 1000, 4H-4H (2006)
Journal of the Chemical Society. Perkin Transactions 1, 459-459 (1993)
Efficient polymer-assisted strategy for the deprotection of protected oligosaccharides.
Hiroshi Tanaka et al.
Angewandte Chemie (International ed. in English), 45(38), 6349-6352 (2006-08-19)
Synthesis of new glycopeptidomimetics based on N-substituted oligoglycine bearing an N-linked lactoside side-chain.
Saha UK and Roy R.
Journal of the Chemical Society. Chemical Communications, 24, 2571-2573 (1995)
Guillaume Jeannotte et al.
The Journal of organic chemistry, 69(14), 4656-4662 (2004-07-03)
Fused heteroarylprolines were prepared starting from 4-oxo-N-(PhF)proline benzyl ester (6, PhF = 9-(9-phenylfluorenyl)) following two approaches. First, allylation of oxoproline 6 followed by Wacker oxidation gave 1,4-dione 8 that was selectively converted to pyrroloproline 10b, pyrrolopyrrole 12, and pyridazinoproline 9.
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service