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Merck
CN

542121

3′-Bromo-5′-chloro-2′-hydroxyacetophenone

97%

Synonym(s):

1-(3-Bromo-5-chloro-2-hydroxyphenyl)ethanone, 5-Chloro-3-bromo-2-hydroxyacetophenone

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About This Item

Linear Formula:
ClC6H2(Br)(OH)COCH3
CAS Number:
59443-15-1
Molecular Weight:
249.49
NACRES:
NA.22
PubChem Substance ID:
24878585
UNSPSC Code:
12352100
MDL number:
MFCD00857068
Assay:
97%

Key Documents

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Product Name

3′-Bromo-5′-chloro-2′-hydroxyacetophenone, 97%

InChI

1S/C8H6BrClO2/c1-4(11)6-2-5(10)3-7(9)8(6)12/h2-3,12H,1H3

SMILES string

CC(=O)c1cc(Cl)cc(Br)c1O

InChI key

FFAVKFQPEOGJOA-UHFFFAOYSA-N

assay

97%

mp

100-103 °C (lit.)

functional group

bromo
chloro
ketone

General description

3′-Bromo-5′-chloro-2′-hydroxyacetophenone is a halogenated aromatic hydroxyl ketone. It participates in the synthesis of racemates of 8-bromo-6-chloro-2-alkyl substituted chroman-4-ones.

Packaging

3′-Bromo-5′-chloro-2′-hydroxyacetophenone (3-bromo-5-chloro-2-hydroxyacetophenone) may be used in the synthesis of corresponding chalcones and structurally related dienones by reacting with appropriate aldehydes.
It may also be used in the preparation of the bioactive 8-bromo-6-chloro-2-substituted 4-chromanone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBN7260V
13212MH
U22414
11715BD
U14983

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Christine Dyrager et al.
Bioorganic & medicinal chemistry, 19(8), 2659-2665 (2011-04-05)
A series of dihalogenated chalcones and structurally related dienones were synthesized and evaluated for their antiproliferative activity in 10 different cancer cell lines and for their effect on microtubule assembly. All compounds showed cytotoxic activity, with IC(50) values in the
Maria Fridén-Saxin et al.
The Journal of organic chemistry, 74(7), 2755-2759 (2009-03-28)
A base-promoted condensation between 2-hydroxyacetophenones and aliphatic aldehydes has been studied. The reaction has been optimized to afford 2-alkyl-substituted 4-chromanones in an efficient manner using microwave heating. Performing the reaction using diisopropylamine in EtOH at 170 degrees C for 1
Maria Fridén-Saxin et al.
Journal of medicinal chemistry, 55(16), 7104-7113 (2012-07-04)
A series of substituted chromone/chroman-4-one derivatives has been synthesized and evaluated as novel inhibitors of SIRT2, an enzyme involved in aging-related diseases, e.g., neurodegenerative disorders. The analogues were efficiently synthesized in a one-step procedure including a base-mediated aldol condensation using
Proline-mediated formation of novel chroman-4-one tetrahydropyrimidines.
Friden-Saxin M, et al.
Tetrahedron, 68(35), 7035-7040 (2012)

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