4-(Trifluoromethyl)thiobenzamide

4-(Trifluoromethyl)thiobenzamide Property

Melting point:

136-137 °C

Boiling point:

246.0±50.0 °C(Predicted)

Density 

1.372±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

pka

12.04±0.29(Predicted)

form 

powder to crystal

color 

Light yellow to Yellow to Green

Sensitive 

Stench

BRN 

4672885

InChI

InChI=1S/C8H6F3NS/c9-8(10,11)6-3-1-5(2-4-6)7(12)13/h1-4H,(H2,12,13)

InChIKey

IPRFNMJROWWFBH-UHFFFAOYSA-N

SMILES

C1(C(N)=S)=CC=C(C(F)(F)F)C=C1

CAS DataBase Reference

72505-21-6(CAS DataBase Reference)

NIST Chemistry Reference

4-(Trifluoromethyl)thiobenzamide(72505-21-6)

Safety

Hazard Codes 

Xn,Xi,T

Risk Statements 

20/21/22-36/37/38

Safety Statements 

36/37/39-26-22-36

RIDADR 

2811

Hazard Note 

Irritant/Stench

HazardClass 

6.1

PackingGroup 

III

HS Code 

29309090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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-(Trifluoromethyl)thiobenzamide Chemical Properties,Usage,Production

Chemical Properties

Yellow crystalline powder

Synthesis

The general procedure for the synthesis of 4-(trifluoromethyl)thiobenzamide from 4-trifluoromethylbenzonitrile was as follows: 500 mg (2.92 mmol) of 4-trifluoromethylbenzonitrile was reacted with 702 mg (8.7 mmol) of sodium thiohydride for 3 hr at 60 °C. Ethanol was used as a solvent during the reaction, and the ethanol was removed by distillation after the reaction was completed. Subsequently, ethyl acetate was added to the reaction mixture and the resulting solution was washed with water. The organic layer was dried with anhydrous magnesium sulfate and then the solvent was removed by distillation. The residue was purified by column chromatography to give 517 mg (95% yield) of 4-(trifluoromethyl)thiobenzamide. The product could be used in the next step of the reaction without further purification. Mass spectrometry (EI) showed a molecular ion peak of 152 (M++1).

References

[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 8, p. 3213 - 3222
[2] Patent: WO2005/40127, 2005, A1. Location in patent: Page/Page column 100-101
[3] Journal of Fluorine Chemistry, 2006, vol. 127, # 1, p. 63 - 67
[4] Patent: WO2004/6922, 2004, A1. Location in patent: Page/Page column 27; 28
[5] RSC Advances, 2018, vol. 8, # 1, p. 170 - 175