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579920

Sigma-Aldrich

3-(Bromoacetyl)coumarin

97%

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Empirical Formula (Hill Notation):
C11H7BrO3
CAS Number:
Molecular Weight:
267.08
MDL number:
PubChem Substance ID:
NACRES:
NA.22

assay

97%

form

solid

mp

164-168 °C (lit.)

SMILES string

BrCC(=O)C1=Cc2ccccc2OC1=O

InChI

1S/C11H7BrO3/c12-6-9(13)8-5-7-3-1-2-4-10(7)15-11(8)14/h1-5H,6H2

InChI key

NTYOLVNSXVYRTJ-UHFFFAOYSA-N

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This Item
550337478075214671
3-(Bromoacetyl)coumarin 97%

579920

3-(Bromoacetyl)coumarin

4-Chloro-3-formylcoumarin 97%

550337

4-Chloro-3-formylcoumarin

3-Acetylcoumarin 96%

214671

3-Acetylcoumarin

form

solid

form

-

form

-

form

solid

mp

164-168 °C (lit.)

mp

126-130 °C (lit.)

mp

202-207 °C (lit.)

mp

119-122 °C (lit.)

General description

3-(Bromoacetyl)coumarin can be synthesized via the bromination of 3-acetylcoumarin in chloroform.

Application

3-(bromoacetyl)coumarin may be used in the synthesis of the following:
  • 3-(bromoacetyl)coumarin oxime via reaction with hydroxylamine hydrochloride in methanol
  • 3-(bromoacetyl)coumarin-O-methyloxime via reaction with O-benzylhydroxylammonium chloride/diluted HCl in methanol
  • 3-(bromoacetyl)coumarin-O-benzyloxime via reaction with O-benzyl hydroxylamine hydrochloride in methanol
  • 3-[2′-(2′′-arylidenehydrazinyl)thiazolyl]coumarins via reaction with benzaldehyde thiosemicarbazones

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Journal of Chemistry, 8(01), 386- 390 (2011)
"Synthesis and Antibacterial Activity of Quinolone-Based Compounds Containing a Coumarin Moiety"
Emami S, et al.
Arch. Pharm. (Weinheim), 341(01), 42-48 (2008)
Ewa Poboży et al.
Mikrochimica acta, 172(3-4), 409-417 (2011-04-08)
Perfluorinated carboxylic acids (PFCAs) represent an important group of persistent perfluorinated organic compounds commonly determined in environmental and biological samples. A reversed-phase HPLC method was developed based on derivatization of the PFCAs with the commercially available fluorescent reagent 3-bromoacetyl coumarin.
Saman Khan et al.
Chemico-biological interactions, 290, 64-76 (2018-05-29)
Coumarin is an important bioactive pharmacophore. It is found in plants as a secondary metabolite and exhibits diverse pharmacological properties including anticancer effects against different malignancies. Therapeutic efficacy of coumarin derivatives depends on the pattern of substitution and conjugation with
Saman Khan et al.
Bioorganic chemistry, 99, 103818-103818 (2020-04-11)
Targeted therapy is a new strategy for cancer treatment that targets chemical entities specific to cancer cells than normal ones. One of the features associated with malignancy is the elevated copper which plays an integral role in angiogenesis. Work is

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