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579920

Sigma-Aldrich

3-(Bromoacetyl)coumarin

97%

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About This Item

Fórmula empírica (notación de Hill):
C11H7BrO3
Número de CAS:
29310-88-1
Peso molecular:
267.08
MDL number:
MFCD00488331
UNSPSC Code:
12352100
PubChem Substance ID:
24881020
NACRES:
NA.22

assay

97%

form

solid

mp

164-168 °C (lit.)

functional group

bromo
ester
ketone

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

Categorías relacionadas

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
GHS05,GHS07

signalword

Danger

hcodes

H302,H318

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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Certificados de análisis (COA)

Lot/Batch Number
0000407033
0000407033
0000302037
0000266306
0000257714

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"Synthesis and Oral Hypoglycemic Activity of 3-[5'-Methyl-2'-aryl-3'-(thiazol-2"-yl amino) thiazolidin-4'-one] coumarin Derivatives"
Kini D and Ghate M
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)
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
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.

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