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Sigma-Aldrich

Phenyl bromoacetate

98%

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About This Item

Linear Formula:
BrCH2CO2C6H5
CAS Number:
620-72-4
Molecular Weight:
215.04
MDL number:
MFCD00192391
UNSPSC Code:
12352100
PubChem Substance ID:
24865235
NACRES:
NA.22

Assay

98%

form

solid

bp

134 °C/15 mmHg (lit.)

mp

31-33 °C (lit.)

density

1.508 g/mL at 25 °C (lit.)

SMILES string

BrCC(=O)Oc1ccccc1

InChI

1S/C8H7BrO2/c9-6-8(10)11-7-4-2-1-3-5-7/h1-5H,6H2

InChI key

UEWYUCGVQMZMGY-UHFFFAOYSA-N

General description

Phenyl bromoacetate is an aromatic ester.

Application

Phenyl bromoacetate may be employed as alkylation reagent in the preparation of 2-(phenoxycarbonyl)methyl triazoles. It may be used in the synthesis of the A-ring of cylindrospermopsin. It may be used in the synthesis of the following 4-thiazolidinones:
  • 2-{2-[1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene]hydrazinyl}-1,3-thiazolidin-4-one
  • 2-{2-[1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene]hydrazinyl}-3-methyl-1,3-thiazolidin-4-one
  • 3-ethyl-2-{2-[1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene]hydrazinyl}-1,3-thiazolidin-4-one
  • 2-{2-[1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene] hydrazinyl}-3-phenyl-1,3-thiazolidin-4-one

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Duen-Ren Hou et al.
Bioorganic & medicinal chemistry letters, 19(3), 1022-1025 (2008-12-20)
This letter reports the new entry of novel 1,2,3-triazole derivatives as CB1 receptor antagonists. The design, synthesis and biological evaluation of N1 and N2 substituted 1,2,3-trizoles are described. The N2 substituted, symmetrical 1,2,3-triazoles are more potent ligands than the unsymmetrical
Synthesis and Antimicrobial Activity Evaluation of Novel 4-Thiazolidinones Containing a Pyrone Moiety.
Nechak R, et al.
Synthetic Communications, 1-11 (2014)
Robert M Williams et al.
ACS symposium series. American Chemical Society, 1009, 420-442 (2010-06-22)
We report the application of diphenyloxazinone glycinate chiral templates to asymmetric syntheses of cylindrospermospin, 7-epi-cylindrospermopsin, 7-deoxycylindrospermopsin, and spirotryprostatins A and B. Synthetic studies toward quinine, nakadomarin A, and palau'amine using these templates are also described.

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