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383384

Sigma-Aldrich

5′-Chloro-2′-hydroxyacetophenone

99%

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About This Item

Linear Formula:
ClC6H3(OH)COCH3
CAS Number:
1450-74-4
Molecular Weight:
170.59
EC Number:
215-916-8
MDL number:
MFCD00067788
UNSPSC Code:
12352100
PubChem Substance ID:
24863960
NACRES:
NA.22

assay

99%

form

solid

bp

126-128 °C/28 mmHg (lit.)

mp

54-56 °C (lit.)

functional group

chloro
ketone

SMILES string

CC(=O)c1cc(Cl)ccc1O

InChI

1S/C8H7ClO2/c1-5(10)7-4-6(9)2-3-8(7)11/h2-4,11H,1H3

InChI key

XTGCUDZCCIRWHL-UHFFFAOYSA-N

General description

5′-Chloro-2′-hydroxyacetophenone (5-chloro-2- hydroxyacetophenone) on condensation with salicylhydrazide yields Schiff base, which is reported to form copper(II) complexes. Dipole moment of 5-chloro-2- hydroxyacetophenone has been evaluated in benzene solution.

Application

5′-Chloro-2′-hydroxyacetophenone (5-chloro-2- hydroxyacetophenone) may be used in the synthesis of:
  • 6-chloro-2-methyl-4H-chrome-4-one
  • 1-(2-hydroxyphenyl)-5-phenyl-2,4-pentadien-1-ones
  • 1-(2-hydroxyphenyl)-5-phenyl-2,4-pentadien-1-ones
  • 2-styrenyl allyl ether

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000195797
MKCT7880
0000256516
0000256515
0000195126

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T Keim et al.
Journal of industrial microbiology & biotechnology, 23(4-5), 359-363 (2001-06-26)
Due to their physicochemical and toxicological properties, polychlorinated dibenzofurans are regarded as a class of compounds providing reason for serious environmental concern. While the nonhalogenated basic structure dibenzofuran is effectively mineralized by appropriate bacterial strains, its polychlorinated derivatives are not.
Nicoletta Desideri et al.
Antiviral chemistry & chemotherapy, 14(4), 195-203 (2003-10-30)
Recently, we identified 2-styrylchromones as a new class of antirhinovirus flavonoids with moderate activity against both rhinovirus groups A and B. In order to improve the antiviral effect of the first series of tested 2-styrylchromones, a hydroxy or methoxy group
Studies on the Intramolecular Hydrogen Bond in Conjugated Systems by the Measurements of Dipole Moments. II. Salicylaldehyde and o-Hydroxyacetophenone
Eda B and Ito K.
Bulletin of the Chemical Society of Japan, 30(2), 164-167 (1957)
A Highly Efficient and Practical Synthesis of Chromene Derivatives Using Ring-Closing Olefin Metathesis.
Sukbok Chang et al.
The Journal of organic chemistry, 63(3), 864-866 (2001-10-24)
Synthesis and characterization of copper (II) complexes with a tridentate schiff base ligand derived from 5-chloro-2-hydroxyacetophenone and salicylhydrazide. X-ray structure of copper (II)(5-chloro-2-hydroxyacetophenone-salicylhydrazide) dimethylformamide.
Dance JM, et al.
Inorgorganica Chimica Acta, 162(2), 239-244 (1989)

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