4-(DIFLUOROMETHOXY)ACETOPHENONE Chemical Properties

Melting point:

18-19°C

Boiling point:

70-72°C 0,5mm

Density 

1.191±0.06 g/cm3(Predicted)

refractive index 

1.4930 to 1.4970

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

color 

Light orange to Yellow to Green

λmax

252nm(EtOH)(lit.)

CAS DataBase Reference

83882-67-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

Hazard Note 

Irritant

HS Code 

2914790090

4-(DIFLUOROMETHOXY)ACETOPHENONE Usage And Synthesis

Chemical Reactivity

4-(DIFLUOROMETHOXY)ACETOPHENONE is a chemical compound that contains the difluoromethoxy group. It has been shown to be a nitrogen-containing heterocycle, which makes it an important part of many pyridine derivatives. The cyclic molecule is also known as 1,2-difluoroethanone.

Synthesis

To a stirred solution of 4-hydroxyacetophenone (5.0 g, 36.76 mmol) in N,N-dimethylformamide (DMF, 50 mL) was added sodium 2-chloro-2,2-difluoroacetate (6.2 g, 40.44 mmol) followed by sodium hydroxide (NaOH, 1.76 g, 44.11 mmol). The reaction mixture was stirred at 100 °C for 14 hours. After completion of the reaction, the mixture was diluted with cold water and the product was extracted with ethyl acetate (EtOAc). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using a 20-30% ethyl acetate/hexane solvent mixture to afford the target compound 1-(4-difluoromethoxyphenyl)ethanone (3.5 g, 51.0% yield) as a colorless liquid.1H NMR (400 MHz, DMSO-d6): δ 8.05-8.01 (m, 2H), 7.59-7.22 (m 3H), 2.50 (s, 3H); LC-MS: m/z 187.0 [M+H]+.

References

[1] Patent: WO2018/165520, 2018, A1. Location in patent: Page/Page column 215-216

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