3',5'-Difluoroacetophenone

3',5'-Difluoroacetophenone Property

Melting point:

34-38 °C(lit.)

Boiling point:

94 °C

Density 

1.206±0.06 g/cm3(Predicted)

refractive index 

1.4876

Flash point:

180 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Low Melting Solid

color 

White to slightly yellow

BRN 

6798740

InChI

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

InChIKey

OXJLDNSPGPBDCP-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC(F)=CC(F)=C1)C

CAS DataBase Reference

123577-99-1(CAS DataBase Reference)

NIST Chemistry Reference

3,5-Difluoroacetophenone(123577-99-1)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38-R36/37/38-36-26

Safety Statements 

26-36-S36-S26-36/37/38

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29147000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3',5'-Difluoroacetophenone Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powde

Uses

3′,5′-Difluoroacetophenone (3,5-Difluoroacetophenone) may be used to synthesize:

• (E)-3-(4-(1,5,9-trithia-13-azacyclohexadecan-13-yl)-phenyl)-1-(3,5-difluorophenyl)prop-2-en-1-one
• 1,3,5-triarylpyrazoline fluorophores containing a 16-membered thiazacrown ligand
• (±)-fluorinated-1-(3-morpholin-4-yl-phenyl)ethylamine
• (E)-1-(3,5-difluorophenyl)-3-(2,4-dimethoxyphenyl) prop-2-en-1-one
• 1-(3,5-difluorophenyl)-4,4,4-trifluorobutane-1,3-dione

General Description

3′,5′-Difluoroacetophenone, also known as 1-(3,5-difluorophenyl)ethanone, is a fluorinated acetophenone.

Synthesis

The general procedure for the synthesis of 3,5-difluoroacetophenone from 1-(3,5-difluorophenyl)ethanol was carried out as follows: a solution of Dess-Martin periodontane (9.66 g, 22.8 mmol) was added batchwise to a solution of 1-(3,5-difluorophenyl)ethanol (3.00 g, 19.0 mmol) in dichloromethane (40 mL) under ice-bath cooling conditions. The reaction mixture was stirred at room temperature for 2 hours. Subsequently, the solvent was removed by concentration under reduced pressure. The residue was purified by silica gel column chromatography using a CombiFlash device eluting with a gradient of ethyl acetate/hexane (0-40%). Purification afforded 3,5-difluoroacetophenone (2.06 g, 69.6% yield) as a colorless oil. Its 1H NMR (300 MHz, CDCl3) data were as follows: δ 7.45 (m, 2H), 7.01 (m, 1H), 2.59 (s, 3H) ppm.

References

[1] Patent: US2014/200227, 2014, A1. Location in patent: Paragraph 1098; 1099