3',5'-DIFLUORO-2'-HYDROXYACETOPHENONE Chemical Properties

Melting point:

53-55°C

Boiling point:

220.8±35.0 °C(Predicted)

Density 

1.346±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

8.93±0.23(Predicted)

form 

powder

color 

Khaki/gold

CAS DataBase Reference

140675-42-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2914500090

3',5'-DIFLUORO-2'-HYDROXYACETOPHENONE Usage And Synthesis

Preparation

This compound can be easily obtained by Fries rearrangement of 2,4-difluorophenyl acetate with aluminium chloride without solvent at 150°, and purified by recrystallization from ethanol (80–90%) ; the 2,4-difluorophenyl acetate is prepared by reaction of acetic anhydride on 2,4-difluorophenol.

Synthesis

General procedure for the synthesis of 1-(3,5-difluoro-2-hydroxyphenyl)ethanone from 2,4-difluorophenyl acetate: a mixture of intermediate 362 (2 g, 11.6 mmol) and aluminum trichloride (2.8 g) was heated under argon protection at 150 °C for 30 min. After completion of the reaction, it was cooled to room temperature and ice water was added cautiously followed by dropwise addition of 1N aqueous hydrochloric acid solution. The mixture was decanted in the presence of toluene and the organic phase was separated and washed sequentially with water and saturated aqueous sodium chloride. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the solid product intermediate 363 (1.5 g). The product was characterized as follows: 1H NMR (300 MHz, CDCl3): δ 12.00 (m, 1H), 7.25 (m, 1H), 7.10 (m, 1H), 2.65 (s, 3H). ir (cm-1): 1651.

References

[1] Journal of Medicinal Chemistry, 2006, vol. 49, # 22, p. 6569 - 6584
[2] Patent: US2017/137385, 2017, A1. Location in patent: Paragraph 0279; 0283; 0284; 0285
[3] Patent: US6191164, 2001, B1

3',5'-DIFLUORO-2'-HYDROXYACETOPHENONE(140675-42-9)Related Product Information

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• 5,6,7,8-TETRAFLUORO-2-METHYL-4-OXO-4H-CHROMENE-3-CARBOXYLIC ACID ETHYL ESTER