4,4'-Difluorobenzhydrol Chemical Properties

Melting point:

43-45 °C(lit.)

Boiling point:

143 °C3 mm Hg(lit.)

Density 

1.2031 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

13.41±0.20(Predicted)

color 

White to Light yellow

BRN 

2332258

InChI

InChI=1S/C13H10F2O/c14-11-5-1-9(2-6-11)13(16)10-3-7-12(15)8-4-10/h1-8,13,16H

InChIKey

WCTZPQWLFWZYJE-UHFFFAOYSA-N

SMILES

C(O)(C1C=CC(F)=CC=1)C1C=CC(F)=CC=1

CAS DataBase Reference

365-24-2(CAS DataBase Reference)

NIST Chemistry Reference

4,4'-Difluorobenzhydrol(365-24-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36/37-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29062900

MSDS

• Language:English Provider:Bis(4-fluorophenyl)methanol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4,4'-Difluorobenzhydrol Usage And Synthesis

Chemical Properties

white to yellowish crystalline flakes or powder

Uses

4-Chloropyridine-3-sulfonyl Chloride can be used for antiinflammatory properties.

General Description

Bis(4-fluorophenyl)methanol is one of the degardation product of flunarizine hydrochloride (FLZ).

Synthesis

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

References

[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 28, p. 5094 - 5096
[2] Synthesis, 2010, # 12, p. 1989 - 1991
[3] Synthetic Communications, 2014, vol. 44, # 5, p. 600 - 609
[4] Organic Letters, 2000, vol. 2, # 5, p. 659 - 661
[5] Patent: , 2016, . Location in patent: Paragraph 0016; 0018; 0019; 0020; 0021; 0022

4,4'-Difluorobenzhydrol(365-24-2)Related Product Information

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• DECAFLUOROBENZHYDROL
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