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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:
Molecular Weight:
170.59
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

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

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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.
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)
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)
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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