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Merck
CN

124230

tert-Butyl bromoacetate

98%

Synonym(s):

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

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About This Item

Linear Formula:
BrCH2COOC(CH3)3
CAS Number:
5292-43-3
Molecular Weight:
195.05
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24847606
EC Number:
226-133-6
Beilstein/REAXYS Number:
1753010
MDL number:
MFCD00000188
Assay:
98%
Form:
liquid

Key Documents

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InChI key

BNWCETAHAJSBFG-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

98%

form

liquid

Quality Level

200

bp

50 °C/10 mmHg (lit.)

density

1.321 g/mL at 25 °C (lit.)

functional group

bromo, ester

Related Categories

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.

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Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
0000231481
0000189538
0000164225
0000164225
0000136651

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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)
Journal of the Chemical Society. Perkin Transactions 1, 459-459 (1993)
SYNTHESIS OF (NITRILOTRIACETIC ACID)-END-FUNCTIONALIZED POLYSTYRENE USING ATOM TRANSFER RADICAL POLYMERIZATION.
Cho HY, et al.
Synthesis, 1000, 4H-4H (2006)
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.
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