2,4-Dichloro-5-fluoroacetophenone Chemical Properties

Melting point:

33-36 °C

Boiling point:

167 °C(lit.)

Density 

1.425 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.546(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Almost white

Specific Gravity

1.425

BRN 

3090042

InChI

InChI=1S/C8H5Cl2FO/c1-4(12)5-2-8(11)7(10)3-6(5)9/h2-3H,1H3

InChIKey

FAKJFAMIABOKBW-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC(F)=C(Cl)C=C1Cl)C

CAS DataBase Reference

704-10-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Flammable

HazardClass 

IRRITANT

HS Code 

29147000

MSDS

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

2,4-Dichloro-5-fluoroacetophenone Usage And Synthesis

Application

2,4-Dichloro-5-fluoroacetophenone is an important chemical raw material used as a pharmaceutical intermediate. It is a major intermediate for the third-generation broad-spectrum and highly effective quinolone antibacterial agents ciprofloxacin and enrofloxacin.

Chemical Properties

white to light yellow cryst. low melting solid

Synthesis

In a 1000 mL four-necked flask, 15 g (0.091 mol) of 2,4-dichlorofluorobenzene was added and cooled to 20°C. The solution was then purified with aluminum chloride. Subsequently, 200.2 g (1.5 mol) of aluminum chloride was added, the temperature was maintained between 20-30°C, and 78.5 g (1.0 mol) of acetyl chloride was slowly added dropwise, with the dropwise process being controlled to be completed in 2 to 3 hours. The reaction mixture was gradually heated to 40°C and maintained for 30 minutes, then slowly warmed to 70°C and maintained for 1~2 hours. Then, the heating was continued slowly to 110°C and the reaction was carried out at 110±2°C for 3~4 hours. After the reaction was completed, it was cooled to room temperature, 500 g of 5% hydrochloric acid solution was added and hydrolyzed at 80~90°C for 2~3 hours. After the hydrolysis product was washed to neutral, the organic phase was separated and purified by secondary distillation and recrystallization to obtain 168 g of 2',4'-dichloro-5'-fluoroacetophenone with a purity of 99.8% and a yield of 89.3%.

References

[1] Patent: CN102249881, 2016, B. Location in patent: Paragraph 0020; 0082-0083
[2] Tetrahedron Letters, 2009, vol. 50, # 21, p. 2525 - 2528
[3] Patent: WO2010/58421, 2010, A2. Location in patent: Page/Page column 20-21
[4] Patent: US6967205, 2005, B1. Location in patent: Page/Page column 25-26

2,4-Dichloro-5-fluoroacetophenone(704-10-9)Related Product Information

• Acetophenone
• 3-Nitroacetophenone
• Trifluoroacetophenone
• 3'-Fluoroacetophenone
• 4-Nitroacetophenone
• 4'-(Trifluoromethyl)acetophenone
• 2',4'-Difluoroacetophenone
• Dichloroacetonitrile
• PIPERACETAZINE (250 MG)
• 4-Fluoroacetophenone
• 4'-Hydroxyacetophenone
• 3'-(Trifluoromethyl)acetophenone
• 4'-Methoxyacetophenone
• 2',4'-Dichloroacetophenone
• METHYL 3-(CYCLOPROPYLAMINO)-2-(2,4-DICHLORO-5-FLUOROBENZOYL)ACRYLATE
• 2,6-Dichloro-3-fluoroacetophenone
• 3',5'-DICHLORO-2'-FLUOROACETOPHENONE,3,5-DICHLORO-2-FLUOROACETOPHENONE
• (Z)-3-CYCLOPROPYLAMINO-2-(2,4-DICHLORO-5-FLUORO-BENZOYL)-ACRYLIC ACID ETHYL ESTER