4-(Trifluoromethoxy)fluorobenzene Chemical Properties

Boiling point:

104-105 °C(lit.)

Density 

1.323 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.394(lit.)

Flash point:

60 °F

storage temp. 

Store below +30°C.

form 

liquid

Specific Gravity

1.323

color 

Clear, colourless

Water Solubility 

Not miscible or difficult to mix in water.

BRN 

2046330

InChI

InChI=1S/C7H4F4O/c8-5-1-3-6(4-2-5)12-7(9,10)11/h1-4H

InChIKey

JULMJGDXANEQDP-UHFFFAOYSA-N

SMILES

C1(F)=CC=C(OC(F)(F)F)C=C1

CAS DataBase Reference

352-67-0(CAS DataBase Reference)

NIST Chemistry Reference

P-fluorophenyl trifluoromethyl ether(352-67-0)

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36/37/39

RIDADR 

UN 1993 3/PG 2

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

3

PackingGroup 

II

HS Code 

29093090

Storage Class

3 - Flammable liquids

Hazard Classifications

Flam. Liq. 2

MSDS

• Language:English Provider:4-(Trifluoromethoxy)fluorobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-(Trifluoromethoxy)fluorobenzene Usage And Synthesis

Uses

It is employed as an active pharmaceutical intermediate.

Synthesis

The general procedure for the synthesis of p-fluorotrifluoromethoxybenzene from 2,2-difluoro-2-(4-fluorophenoxy)acetic acid was as follows: a stir bar was added to a 5 mL microwave vial in an argon-protected glove box and sealed. Selectfluor (177.1 mg, 0.5 mmol, 2.0 eq.), silver trifluoromethanesulfonate (12.8 mg, 0.05 mmol, 20 mol%), and 2,2-difluoro-2-(4-fluorophenoxy)acetic acid (0.25 mmol, 1.0 eq.) were added sequentially. The vial was charged with dichloromethane (1.8 mL), trifluoroacetic acid (76.5 μL, 1.0 mmol, 4.0 equiv) and water (0.2 mL). The reaction mixture was heated at 55 °C for 1 hour. After completion of the reaction, the mixture was cooled to room temperature, diluted with dichloromethane (4 mL), washed sequentially with water (3 x 5 mL) and brine (5 mL), dried over anhydrous magnesium sulfate and filtered. The dried organic phase was concentrated on a rotary evaporator. The crude product obtained was dissolved in a small amount of dichloromethane and purified by passing through a silica gel column (10 g, Biotage), first dried with air and then eluted with pentane. The fractions containing the pure product were combined and the solvent evaporated to give pure p-fluorotrifluoromethoxybenzene.

References

[1] Organic Letters, 2016, vol. 18, # 15, p. 3754 - 3757
[2] Organic Letters, 2016, vol. 18, # 18, p. 4570 - 4573
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 33, p. 9758 - 9762
[4] Angew. Chem., 2016, vol. 128, # 33, p. 9910 - 9914,5
[5] Journal of Fluorine Chemistry, 2017, vol. 203, p. 130 - 135

4-(Trifluoromethoxy)fluorobenzene(352-67-0)Related Product Information

• 2-FLUORO-5-(TRIFLUOROMETHOXY)BENZALDEHYDE
• 4-(Trifluoromethoxy)fluorobenzene
• 2-FLUORO-5-(TRIFLUOROMETHOXY)PHENOL
• 2-FLUORO-5-(TRIFLUOROMETHOXY)BENZYLAMINE
• 2-FLUORO-5-(TRIFLUOROMETHOXY)BENZONITRILE
• 2-FLUORO-5-(TRIFLUOROMETHOXY)PHENYLACETIC ACID
• 2-FLUORO-5-(TRIFLUOROMETHOXY)BENZOIC ACID
• 2-FLUORO-5-(TRIFLUOROMETHOXY)BENZYL BROMIDE
• 2-FLUORO-5-(TRIFLUOROMETHOXY)PHENYLBORONIC ACID
• 1-Bromo-3-fluoro-4-trifluoromethoxybenzene
• 2-(Trifluoromethoxy)fluorobenzene
• 3-(Trifluoromethoxy)fluorobenzene, 97+%,3-(TRIFLUOROMETHOXY)FLUOROBENZENE
• (Trifluoromethoxy)benzene
• 2-FLUORO-5-(TRIFLUOROMETHOXY)PHENYLACETONITRILE
• 1-BROMO-2-FLUORO-5-(TRIFLUOROMETHOXY)BENZENE
• 2-FLUORO-5-(TRIFLUOROMETHOXY)BENZOYL CHLORIDE
• 2-FLUORO-5-(TRIFLUOROMETHOXY)BENZYL ALCOHOL
• 2-FLUORO-5-(TRIFLUOROMETHOXY)BENZAMIDE