2-Chloro-2',4'-difluoroacetophenone Chemical Properties

Melting point:

44-48 °C(lit.)

Boiling point:

240.9±25.0 °C(Predicted)

Density 

1.3544 (estimate)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly)

form 

Solid

color 

Light Brown

Sensitive 

Lachrymatory

BRN 

1943217

InChI

InChI=1S/C8H5ClF2O/c9-4-8(12)6-2-1-5(10)3-7(6)11/h1-3H,4H2

InChIKey

UENGBOCGGKLVJJ-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=C(F)C=C1F)CCl

CAS DataBase Reference

51336-94-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-37

Safety Statements 

26-36/37/39-45-25-27

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

10-21

Hazard Note 

Corrosive/Irritant/Lachrymatory

HazardClass 

8

PackingGroup 

II

HS Code 

29147000

MSDS

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

2-Chloro-2',4'-difluoroacetophenone Usage And Synthesis

Description

2-Chloro-2′,4′-difluoroacetophenone was used in the synthesis of allyl alcohol1. It can also be tested for inhibition of protein tyrosine phosphatases SHP-1 and PTP1B2.

Chemical Properties

white crystalline powder

Uses

2-Chloro-2′,4′-difluoroacetophenone was used in the synthesis of allyl alcohol.

Uses

A α-haloacetophenone derivatives tested for inhibition of protein tyrosine phosphatases SHP-1 and PTP1B.

Synthesis

In a 250 mL four-necked flask equipped with a thermometer, a constant pressure dropping funnel, and a reflux condenser (with a drying tube), 1,3-difluorobenzene (0.1 mol, 14.7 g) and anhydrous aluminum trichloride (0.17 mol, 22.7 g) were added. The mixture was stirred at 30-35°C for 0.5 hours. Subsequently, chloroacetyl chloride (0.12 mol, 13.56 g) was slowly added dropwise to maintain the reaction temperature. After the dropwise addition was completed, the temperature was raised to 50-55 °C and the reaction was continued with stirring until no hydrogen chloride gas escaped, a reaction time of about 5 hours. The reaction mixture was cooled to below 5°C in an ice-water bath, and acid hydrolysis was carried out by slowly dropping 3 mol/L hydrochloric acid (20 mL), controlling the rate of dropwise acceleration to keep the temperature of the mixture low. The acid-hydrolyzed mixture was poured into a beaker and distilled water was added to precipitate the solid. After filtration and drying under reduced pressure, 16.9 g of light yellow powdery solid was obtained in 89.3% yield. Finally, the light yellow powdery solid was recrystallized with hexane to give bright yellow crystalline 2'-chloro-2,4-difluoroacetophenone.

References

[1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 2, p. 372 - 381
[2] Tetrahedron Asymmetry, 2010, vol. 21, # 13-14, p. 1649 - 1665
[3] Patent: CN106187924, 2016, A. Location in patent: Paragraph 0026; 0027
[4] Patent: CN102796080, 2016, B. Location in patent: Paragraph 0040-0042
[5] Journal of Organic Chemistry, 1995, vol. 60, # 10, p. 3000 - 3012

2-Chloro-2',4'-difluoroacetophenone (51336-94-8)Related Product Information

• 4'-Bromoacetophenone
• 3'-Chloroacetophenone
• 3'-Fluoroacetophenone
• 1-(2,6-Difluorophenyl)ethan-1-one
• 2',4'-Difluoroacetophenone
• 4-Nitroacetophenone
• 3-Nitroacetophenone
• 4-Fluoroacetophenone
• 2-Chloroacetophenone
• 4'-Hydroxyacetophenone
• Trifluoroacetophenone
• 2',4'-Dichloroacetophenone
• 4'-(Trifluoromethyl)acetophenone
• Acetophenone
• 2'-Chloroacetophenone
• 6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine
• Voriconazole Impurity 53
• Voriconazole