4-(Trifluoromethylthio)aniline Chemical Properties

Boiling point:

102-103 °C/8 mmHg (lit.)

Density 

1.351 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.528(lit.)

Flash point:

224 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

Liquid

pka

2.79±0.10(Predicted)

Specific Gravity

1.351

color 

Clear colorless to yellow

Water Solubility 

insoluble

BRN 

2208859

InChI

InChI=1S/C7H6F3NS/c8-7(9,10)12-6-3-1-5(11)2-4-6/h1-4H,11H2

InChIKey

OHHHTUXVBNGOGI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

372-16-7(CAS DataBase Reference)

NIST Chemistry Reference

Benzenamine, 4-[(trifluoromethyl)thio]-(372-16-7)

Safety Information

Hazard Codes 

Xn,T,Xi

Risk Statements 

20/21/22

Safety Statements 

36-36/37

RIDADR 

UN2810

WGK Germany 

3

Hazard Note 

Toxic

HazardClass 

6.1

PackingGroup 

III

HS Code 

29309090

MSDS

• Language:English Provider:4-Aminophenyltrifluoromethylsulfide
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-(Trifluoromethylthio)aniline Usage And Synthesis

Uses

p-Trifluoromethylthioaniline is a useful compound as a manufacturing intermediate for pesticides such as insecticides and acaricides.

Chemical Properties

clear colorless to yellow liquid

General Description

4-(Trifluoromethylthio)aniline is a 4-substituted aniline derivative.

Synthesis

General procedure for the synthesis of 4-((trifluoromethyl)thio)aniline from 4-trifluoromethylthio nitrobenzene: A palladium-carbon catalyst (10% Pd/C, 3.5 g) was added to a solution of 4-nitrophenyl trifluoromethyl sulfide (33.5 g, 0.15 mol) in ethanol (400 mL). The reaction mixture was placed in an autoclave and hydrogenated in a hydrogen atmosphere at 40 atm at room temperature for 8 hours. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filter cake was washed well with ethanol. The filtrate and washings were combined and concentrated under reduced pressure to remove the solvent. The residue was washed with water to give 28.4 g (98% yield) of 4-aminophenyl trifluoromethyl sulfide as a brown liquid. The product was characterized as follows: melting point: 110-112 °C/1.70 KPa (literature value: b.p. 113 °C/1.73 KPa); 1H NMR (300 MHz, CDCl3) δ 7.62 (d, J = 8.30 Hz, 2H), 7.42 (dd, J = 8.30 Hz, J = 1.90 Hz, 2H), 3.84 (s, 2H NH2); 19F NMR (220 MHz, CDCl3) δ 44.5 (s, 3F, SCF3); 13C NMR (75 MHz, CDCl3) δ 149.1, 138.2, 126.7, 115.3, 111.3.

References

[1] Journal of Fluorine Chemistry, 2007, vol. 128, # 6, p. 636 - 640
[2] Asian Journal of Chemistry, 2017, vol. 29, # 1, p. 91 - 93
[3] Zhurnal Obshchei Khimii, 1952, vol. 22, p. 2216,2219; engl. Ausg. S. 2273, 2276
[4] Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 1967, vol. 23, p. 1351 - 1372

4-(Trifluoromethylthio)aniline(372-16-7)Related Product Information

• o-Toluidine
• 4-(Trifluoromethoxy)aniline
• 2-Fluoroaniline
• 4-(Trifluoromethylthio)phenol
• 4-Aminobenzotrifluoride
• 3-Fluoroaniline
• p-Toluidine
• 4-Fluoroaniline
• Aniline
• p-Anisidine
• 3-Aminobenzotrifluoride
• 4-(TRIFLUOROMETHYLSULFONYL)ANILINE
• 3-CHLORO-4-(TRIFLUOROMETHYLTHIO)ANILINE
• 4-(Trifluoromethylthio)nitrobenzene
• 3-(Trifluoromethylthio)aniline, 97+%,3-(TRIFLUOROMETHYLTHIO)ANILINE
• 2-(Trifluoromethylthio)aniline, 97+%,2-(TRIFLUOROMETHYLTHIO)ANILINE
• N,N-DIMETHYL-4-(TRIFLUOROMETHYLTHIO)-ANILINE
• 4-(TRIFLUOROMETHYLTHIO)PHENYL ISOCYANATE