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124230

Sigma-Aldrich

tert-Butyl bromoacetate

98%

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Synonym(s):
Bromoacetic acid tert-butyl ester, t-Butyl bromoacetate, tert-Butyl 2-bromoacetate
Linear Formula:
BrCH2COOC(CH3)3
CAS Number:
Molecular Weight:
195.05
Beilstein/REAXYS Number:
1753010
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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1 of 4

This Item
13397317020419885
vibrant-m

124230

tert-Butyl bromoacetate

vibrant-m

133973

Ethyl bromoacetate

vibrant-m

17020

Ethyl bromoacetate

vibrant-m

419885

tert-Butyl propiolate

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

density

1.321 g/mL at 25 °C (lit.)

density

1.506 g/mL at 25 °C (lit.)

density

1.506 g/mL at 25 °C (lit.)

density

0.919 g/mL at 25 °C (lit.)

refractive index

n20/D 1.445 (lit.)

refractive index

n20/D 1.451 (lit.)

refractive index

n20/D 1.451 (lit.)

refractive index

n20/D 1.418 (lit.)

form

liquid

form

liquid

form

-

form

liquid

bp

50 °C/10 mmHg (lit.)

bp

159 °C (lit.)

bp

159 °C (lit.)

bp

52-53 °C/27 mmHg (lit.)

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.

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

120.2 °F - closed cup

flash_point_c

49 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Sigma-Aldrich

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Sigma-Aldrich

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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)
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 (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)
Shuo Fang et al.
International journal of pharmaceutics, 493(1-2), 460-465 (2015-08-11)
A novel dual drug-tailed betaine conjugate amphiphile has been firstly synthesized in which the polar headgroup is derived from glycine betaine and the hydrophobic tails are chlorambucil molecules. The newly prepared conjugate undergoes self-assembly to form stable liposome-like nanocapsules as

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