2,2',4'-Trichloroacetophenone Chemical Properties

Melting point:

47-54 °C(lit.)

Boiling point:

130-135 °C4 mm Hg(lit.)

Density 

1,312 g/cm³

refractive index 

1.5510 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

60 mg/L (20°C)

form 

Solid

color 

beige to yellow

PH

4.96 at 25.1℃ and 10g/L

Water Solubility 

60 mg/L (20 ºC)

Sensitive 

Lachrymatory

BRN 

957098

CAS DataBase Reference

4252-78-2(CAS DataBase Reference)

EPA Substance Registry System

Ethanone, 2-chloro-1-(2,4-dichlorophenyl)- (4252-78-2)

Safety Information

Hazard Codes 

Xi,C,N,T

Risk Statements 

37/38-41-43-51/53-34-23/24/25

Safety Statements 

26-36/37/39-61-45-37/39

RIDADR 

1759

WGK Germany 

3

Hazard Note 

Corrosive/Lachrymatory

HazardClass 

8

PackingGroup 

III

HS Code 

29147090

MSDS

• Language:English Provider:2,4-Dichlorophenacyl chloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,2',4'-Trichloroacetophenone Usage And Synthesis

Chemical Properties

yellow crystalline powde

Uses

α,2,4-Trichloroacetophenone is a reagent used in the synthesis of isoconazole, a potent antifungal agent.

General Description

Off-white crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2,2',4'-Trichloroacetophenone is incompatible with strong oxidizers and strong bases. .

Fire Hazard

2,2',4'-Trichloroacetophenone is probably combustible.

Synthesis

To a three-necked flask equipped with a stirrer was added 1,3-dichlorobenzene (147 g), chloroacetyl chloride (113 g) and methylene chloride (750 mL) at room temperature. Under stirring, anhydrous aluminum trichloride (147 g) was added in batches. After the addition was complete, the reaction mixture was heated to reflux and maintained for 3 hours to ensure complete reaction. Upon completion of the reaction, the mixture was quenched by carefully pouring it into ice water. Subsequently, the organic and aqueous phases were separated. The organic phase was washed sequentially with deionized water (500 mL x 2) and saturated sodium bicarbonate solution (500 mL x 2) to remove acidic impurities. The washed organic phase was dried with anhydrous sodium sulfate and filtered to remove the desiccant. The filtrate was concentrated by rotary evaporation and petroleum ether (1200 mL) was added to the residue. The mixture was cooled to room temperature and placed in a refrigerator overnight to promote crystallization. The following day, the crystallized product was collected by filtration and washed with a small amount of cold petroleum ether. Ultimately, the product was dried under vacuum to give 2,2',4'-trichloroacetophenone (193 g, 86% yield) in the form of an off-white solid.

References

[1] Journal of Chemical Sciences, 2015, vol. 127, # 12, p. 2251 - 2260
[2] Patent: CN105566309, 2016, A. Location in patent: Paragraph 0003; 0007
[3] Chemische Berichte, 1907, vol. 40, p. 1703
[4] Tetrahedron Asymmetry, 2003, vol. 14, # 24, p. 3861 - 3866
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5368 - 5371

2,2',4'-Trichloroacetophenone(4252-78-2)Related Product Information

• 2',4'-Dichloroacetophenone
• Choline chloride
• Sodium chloride
• Ammonium chloride
• Calcium chloride
• 3-Nitroacetophenone
• 4-Nitroacetophenone
• 4'-Hydroxyacetophenone
• 4'-Chloroacetophenone
• 4'-Bromoacetophenone
• 3'-Chloroacetophenone
• 2-Chloroacetophenone
• Oxalyl chloride
• L-PICEIN
• 2-Bromoacetophenone
• Dichloroacetonitrile
• Potassium chloride
• Zinc chloride