4-(Trifluoromethoxy)benzonitrile

4-(Trifluoromethoxy)benzonitrile Property

Boiling point:

192-193 °C(lit.)

Density 

1.285 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.452(lit.)

Flash point:

181 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

color 

Colorless to Almost colorless

BRN 

2832939

InChI

InChI=1S/C8H4F3NO/c9-8(10,11)13-7-3-1-6(5-12)2-4-7/h1-4H

InChIKey

XWHIXOMWXCHJPP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

332-25-2(CAS DataBase Reference)

EPA Substance Registry System

Benzonitrile, 4-(trifluoromethoxy)- (332-25-2)

Safety

Hazard Codes 

Xn,T,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39-45

RIDADR 

3276

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

4-(Trifluoromethoxy)benzonitrile Chemical Properties,Usage,Production

Chemical Properties

clear light yellow liquid

General Description

4-(Trifluoromethoxy)benzonitrile serves as an intermediate in the synthesis of fluvoxamine.

Synthesis

To a 25 mL Schlenk tube equipped with a magnetic stirrer were sequentially added CuCl (0.05 mmol, 5 mol%), DABCO (0.10 mmol, 10 mol%) and 4-HO-TEMPO (0.05 mmol, 5 mol%). Subsequently, a solution of acetonitrile (2 mL) with 4-trifluoromethoxybenzyl alcohol (1 mmol) and ammonia (25-28%, 3 mmol, 3.0 equiv) was added. The reaction mixture was stirred at room temperature for 24 h under balloon protection. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was diluted with water and extracted with ethyl acetate. The organic layers were combined and dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the crude product was purified by column chromatography to give p-trifluoromethoxybenzonitrile.

References

[1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 18, p. 3892 - 3896
[2] Chinese Chemical Letters, 2018, vol. 29, # 3, p. 464 - 466