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349712

Sigma-Aldrich

Benzyl chloroacetate

99%

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Linear Formula:
ClCH2CO2CH2C6H5
CAS Number:
140-18-1
Molecular Weight:
184.62
EC Number:
205-400-0
MDL number:
MFCD00157062
PubChem Substance ID:
24861702

Assay

99%

refractive index

n20/D 1.525 (lit.)

bp

90 °C/1 mmHg (lit.)

density

1.215 g/mL at 25 °C (lit.)

SMILES string

ClCC(=O)OCc1ccccc1

InChI

1S/C9H9ClO2/c10-6-9(11)12-7-8-4-2-1-3-5-8/h1-5H,6-7H2

InChI key

SOGXBRHOWDEKQB-UHFFFAOYSA-N

Related Categories

General description

Benzyl chloroacetate is an ester.

Application

Benzyl chloroacetate may be used:
  • in the synthesis of monoesters of phosphonoacetic acid
  • in the synthesis of N-benzoyl-glycyl- hydroxyl acetic acid, ester substrate for carboxypeptidase Y catalyzed peptide synthesis
  • as reagent in the total syntheses of the (±)-di-O-methyl ethers of the norlignans sequirin-A, agatharesinol, and hinokiresinol, and of (±)-tri-O-methyl sequirin-E

Regulatory Information

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Influence of the substrate structure on carboxypeptidase Y catalyzed peptide bond formation.
Breddam K, et al.
Carlsberg Research Communications, 45(5), 361-367 (1980)
Stereoselective total syntheses of the (?)-di-O-methyl ethers of agatharesinol, sesquirin-A, and hinokiresinol, and of (?)-tri-O-methylsequirin-E, characteristic norlignans of coniferae.
Beracierta AP and Whiting DA.
Journal of the Chemical Society. Perkin Transactions 1, 10, 1257-1263 (1978)
T R Herrin et al.
Journal of medicinal chemistry, 20(5), 660-663 (1977-05-01)
The synthesis of monoesters (P and C) of phosphonoacetic acid (PA) is given. The carboxyl esters were prepared by two methods: the reaction of chloroacetates with tris(trimethylsilyl) phosphite, followed by hydrolysis; and by the acid-catalyzed esterification of PA with the

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