1-(2,6-Difluorophenyl)ethan-1-one Chemical Properties

Melting point:

52-55°C

Boiling point:

76-79 °C15 mm Hg(lit.)

Density 

1.197 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.48(lit.)

Flash point:

170 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Liquid

Specific Gravity

1.197

color 

Clear colorless to slightly yellow

Water Solubility 

Slightly soluble in water.

BRN 

2046068

InChI

InChI=1S/C8H6F2O/c1-5(11)8-6(9)3-2-4-7(8)10/h2-4H,1H3

InChIKey

VGIIILXIQLXVLC-UHFFFAOYSA-N

SMILES

C1C(F)=C(C(=O)C)C(F)=CC=1

CAS DataBase Reference

13670-99-0(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 1-(2,6-difluorophenyl)-(13670-99-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29147000

MSDS

• Language:English Provider:1-(2,6-Difluorophenyl)ethan-1-one
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-(2,6-Difluorophenyl)ethan-1-one Usage And Synthesis

Chemical Properties

Clear colourless to light yellow liquid

Uses

2?,6?-Difluoroacetophenone was used in the synthesis of 2-amino-4-alkyl- and 2-amino-4-arylquinazolines.

General Description

2′,6′-Difluoroacetophenone undergoes ruthenium-catalyzed phenylation with phenylboronate via carbon-fluorine bond cleavage to yield 2′,6′-diphenylacetophenone.

Synthesis

GENERAL STEPS: Magnesium chloride (1.65 g, 17.3 mmol) was added to a solution of diethyl malonate (1.24 g, 7.7 mmol) in ethyl acetate (20 mL) and the mixture was stirred at room temperature for 30 minutes. Subsequently, triethylamine (2.35 mL, 16.7 mmol) was added and stirring was continued for 30 minutes. The reaction mixture was cooled to 0 °C and a solution of ethyl acetate (5 mL) of 2,6-difluorobenzoyl chloride (1.0 g, 5.6 mmol) was slowly added dropwise over a period of 15 min, ensuring that the internal temperature did not exceed 5 °C. After dropwise addition, the reaction mixture was returned to room temperature and stirred for 3 hours. Upon completion of the reaction, the reaction was quenched with 1N hydrochloric acid (50 mL) and extracted with ethyl acetate (100 mL). The organic phase was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the intermediate (1.97 g) as a colorless oil. The oil was dissolved in acetonitrile (25 mL), water (2 mL) was added, and the solution was transferred to a pressure reactor and sealed. The mixture was heated to 150 °C and kept for 1 hour. At the end of the reaction, it was cooled to room temperature and the pressure was released. The yield of 2,6-difluoroacetophenone was determined to be 874 mg (100% yield) by HPLC weight analysis.

References

[1] Patent: WO2013/85686, 2013, A1. Location in patent: Page/Page column 22

1-(2,6-Difluorophenyl)ethan-1-one(13670-99-0)Related Product Information

• 2',6'-DIFLUOROPROPIOPHENONE
• 2',3',4',5',6'-PENTAFLUOROACETOPHENONE
• Ethyl (pentafluorobenzoyl)acetate
• 1-(2,6-Difluorophenyl)ethan-1-one
• 2',4',6'-TRIFLUOROACETOPHENONE
• 2,3,4,5,6-PENTAFLUOROBENZOPHENONE
• 2,6-DIFLUOROBENZOPHENONE
• PENTAFLUOROPHENACYL BROMIDE
• DECAFLUOROBENZOPHENONE
• 2',3',6'-TRIFLUOROPROPIOPHENONE
• 2',3',6'-TRIFLUOROACETOPHENONE
• 2'',4'',6''-TRIFLUOROPROPIOPHENONE
• 4-AMINO-3,5-DIFLUOROACETOPHENONE
• 3'-CHLORO-2',6'-DIFLUOROACETOPHENONE
• 2-CHLORO-2,2-DIFLUOROACETOPHENONE
• 2-Chloro-2',4'-difluoroacetophenone
• 2-CHLORO-2',5'-DIFLUOROACETOPHENONE
• 2,4-Difluoro-alpha-(1H-1,2,4-triazolyl)acetophenone