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245631

Sigma-Aldrich

Benzyl bromoacetate

96%

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Synonym(s):
Bromoacetic acid benzyl ester
Linear Formula:
BrCH2COOCH2C6H5
CAS Number:
5437-45-6
Molecular Weight:
229.07
Beilstein:
973658
EC Number:
226-611-4
MDL number:
MFCD00000190
UNSPSC Code:
12352100
PubChem Substance ID:
24854747
NACRES:
NA.22

Quality Level

200

Assay

96%

form

liquid

refractive index

n20/D 1.544 (lit.)

bp

166-170 °C/22 mmHg (lit.)

density

1.446 g/mL at 25 °C (lit.)

SMILES string

BrCC(=O)OCc1ccccc1

InChI

1S/C9H9BrO2/c10-6-9(11)12-7-8-4-2-1-3-5-8/h1-5H,6-7H2

InChI key

JHVLLYQQQYIWKX-UHFFFAOYSA-N

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Application

Benzyl bromoacetate was used in the alkylation of (-)-2,3-O-isopropylidene-D-threitol that afforded lipopeptide, 2-[(4R,5R)-5-({[(9H-fluoren-9-yl)methoxy]carbonylaminomethyl}-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]acetic acid.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Toru Masaka et al.
Chemical & pharmaceutical bulletin, 61(11), 1184-1187 (2013-08-28)
A new component for the solid phase peptide synthesis of lipopeptide, 2-[(4R,5R)-5-({[(9H-fluoren-9-yl)methoxy]carbonylaminomethyl}-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]acetic acid (2), was designed and synthesized from (-)-2,3-O-isopropylidene-D-threitol (3) in 4 steps. The key step was the selective alkylation of 3 with benzyl bromoacetate in the presence of
Michael Kahnt et al.
Molecules (Basel, Switzerland), 24(12) (2019-06-20)
In this study, we report the synthesis of several amine-spacered conjugates of ursolic acid (UA) and 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA). Thus, a total of 11 UA-DOTA conjugates were prepared holding various oligo-methylene diamine spacers as well as different substituents at the

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