4-Chlorobenzhydrylchloride Chemical Properties

Boiling point:

159-160 °C2 mm Hg(lit.)

Density 

1.239 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.603(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)

form 

clear liquid

color 

Colorless to Light yellow to Light orange

Water Solubility 

IMMISCIBLE

Sensitive 

Moisture Sensitive

BRN 

2050236

CAS DataBase Reference

134-83-8(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-chloro-4-(chlorophenylmethyl)-(134-83-8)

EPA Substance Registry System

Benzene, 1-chloro-4-(chlorophenylmethyl)- (134-83-8)

Safety Information

Hazard Codes 

C

Risk Statements 

34-36/37-36

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29036990

MSDS

• Language:English Provider:Chloro(4-chlorophenyl)phenylmethane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Chlorobenzhydrylchloride Usage And Synthesis

Chemical Properties

clear light yellow liquid

Uses

1-Chloro-4-(chlorophenylmethyl)benzene is used in the synthesis of novel benzhydrylpiperazine derivatives as cytotoxic compounds in the treatment of various cancers.

Preparation

Preparation of 4-Chlorobenzhydryl Chloride (4-CBC): The 4-chlorobenzhydrol (4-CB) in 15 mL of toluene, obtained from the previous step, was mixed with 10 mL of conc. HCl at 60oC maintained at the same temperature for 2.5 h. The reaction mixture was cooled to 20oC to separate into organic and aqueous layers. The toluene layer was washed with 10 % aq. sodium carbonate to pH 7, dried over anhydrous sodium sulphate and taken to next step without isolation.

Synthesis

GENERAL METHODS: NaBH4 (0.6 mol) was added batchwise to a stirred solution of benzophenone (1.0 mol) in methanol (2 vol) at room temperature for 45 min. The reaction mixture was stirred at ambient temperature for 2-3 h (progress of the reaction was monitored by TLC) and subsequently diluted with water (750 mL) and pH adjusted with acetic acid to 4. The reaction mixture was extracted with dichloromethane (2 x 400 mL). The organic layer was washed with water (200 mL), dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the pure diphenylmethanol derivative as a white to off-white solid in 93-97% yield. To a stirred solution of diphenylmethanol derivative (1.0 mol) in toluene (370 mL) at room temperature was sequentially added concentrated HCl (35% aqueous solution, 370 mL) and tetrabutylammonium bromide (0.01 mol). The reaction mixture was stirred at 40-45 °C for 6-7 hours. After confirming the completion of the reaction by TLC, the mixture was cooled to room temperature. The organic layer was separated and concentrated under vacuum to afford the crude diphenylmethyl chloride derivative as a light brown liquid in 95-97% yield. Anhydrous piperazine (5.0 mol) was slowly added to a solution of diphenylmethyl chloride derivative (0.96 mol) in toluene (380 mL) at 60-70 °C for 45-60 minutes. The resulting mixture was heated with stirring at 90-100°C for 8-10 hours. After completion of the reaction, the mixture was cooled and water (380 mL) was added to separate the organic layer. The organic layer was washed with a mixture of concentrated HCl and water (1:1, 2 x 350 mL) and neutralized with 20% NaOH solution (750 mL). The aqueous layer was again extracted with toluene (2 × 300 mL), and the combined organic layers were dried with anhydrous sodium sulfate and concentrated in vacuum to afford the pure diphenylmethylpiperazine compounds (2a-c) as white to off-white solids in 88% yield.

References

[1] Australian Journal of Chemistry, 2006, vol. 59, # 7, p. 445 - 456
[2] Journal of the American Chemical Society, 1928, vol. 50, p. 1804
[3] Journal of the American Chemical Society, 1928, vol. 50, p. 1804
[4] Synthesis, 1976, p. 326 - 329
[5] Journal of Medicinal and Pharmaceutical Chemistry, 1962, vol. 5, p. 1008 - 1015

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