1-(5-Chloro-2-hydroxyphenyl)ethanone Chemical Properties

Melting point:

54-56 °C(lit.)

Boiling point:

126-128 °C28 mm Hg(lit.)

Density 

1.2315 (rough estimate)

refractive index 

1.5590 (estimate)

Flash point:

107-109°C/12mm

storage temp. 

Sealed in dry,Room Temperature

form 

Solid

pka

9.72±0.18(Predicted)

BRN 

1365589

InChI

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

InChIKey

XTGCUDZCCIRWHL-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC(Cl)=CC=C1O)C

CAS DataBase Reference

1450-74-4(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 1-(5-chloro-2-hydroxyphenyl)-(1450-74-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29147000

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1-(5-Chloro-2-hydroxyphenyl)ethanone Usage And Synthesis

Chemical Properties

slightly yellow crystalline powder or chunks

Uses

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

Preparation

Preparation by Fries rearrangement of 4-chlorophenyl acetate with aluminium chloride without solvent between 110° and 200°(90–100% yield).

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.

Synthesis

General procedure for the synthesis of 5'-chloro-2'-hydroxyacetophenone from acetic acid-4-chlorophenyl ester: Acetic acid-4-chlorophenyl ester (10 g, 0.091 mol) was placed in a 500 ml round-bottomed flask with aluminum chloride (14.56 g, 0.11 mol). The mixture was heated in an oil bath at 140-150°C for 5-6 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) using ethyl acetate:hexane as the unfolding agent. Upon completion of the reaction, the reaction mixture was quenched with crushed ice and the solid product was extracted with ethyl acetate (2 x 50 mL). The organic phases were combined, washed with saturated brine solution (2 x 15 mL) and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by recrystallization from aqueous solution. The yield is 90% and the melting point is 54-56°C.

References

[1] Chinese Chemical Letters, 2016, vol. 27, # 7, p. 1058 - 1063
[2] Synthesis, 1985, # 9, p. 901 - 902
[3] Tetrahedron, 2011, vol. 67, # 3, p. 641 - 649
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 2, p. 184 - 185
[5] Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 2, p. 151 - 156

1-(5-Chloro-2-hydroxyphenyl)ethanone(1450-74-4)Related Product Information

• 6-CHLOROCHROMAN-4-ONE
• 6,8-DICHLORO-3-FORMYLCHROMONE
• 5-Chloro-2-hydroxybenzophenone
• (+)-Griseofulvin
• 1-(5-Chloro-2-hydroxyphenyl)ethanone
• 3',5'-DICHLORO-2'-HYDROXYACETOPHENONE
• 2-AMINO-6-CHLORO-3-FORMYLCHROMONE
• MECLOCYCLINE SULFOSALICYLATE SALT
• Demeclocycline hydrochloride
• 5-CHLORO-BENZOFURAN-3-ONE
• Chlortetracycline hydrochloride
• 5-CHLORO-2-HYDROXY-4-METHYLBENZOPHENONE
• 1-(3-bromo-5-chloro-2-hydroxyphenyl)ethanone,1-(3-bromo-5-chloro-2-hydroxyphenyl)ethanone, 5-Chloro-3-bromo-2-hydroxyacetophenone
• 2-Chloro-3',4'-dihydroxyacetophenone
• 2-BROMO-1-(5-CHLORO-2-HYDROXYPHENYL)ETHANONE
• 1-(2-Chloro-6-hydroxyphenyl)ethanone
• 2'-Chloro-4'-hydroxyacetophenone
• 1-(4-CHLORO-2-HYDROXYPHENYL)ETHANONE