4-Fluorothiophenol Chemical Properties

Melting point:

43-46°C

Boiling point:

164-168 °C

Density 

1.203 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.550(lit.)

Flash point:

130 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

soluble in Chloroform, Methanol

form 

Liquid

pka

6.40±0.10(Predicted)

Specific Gravity

1.203

color 

Clear colorless to light yellow

Water Solubility 

Not miscible or difficult to mix in water.

Sensitive 

Stench

BRN 

1446350

InChIKey

OKIHXNKYYGUVTE-UHFFFAOYSA-N

CAS DataBase Reference

371-42-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

10-36/37/38

Safety Statements 

26-36-45-16-7/9

RIDADR 

UN 3336 3/PG 3

WGK Germany 

3

F 

9-13-23

Hazard Note 

Irritant/Stench

TSCA 

N

HazardClass 

3

PackingGroup 

III

HS Code 

29309070

MSDS

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

4-Fluorothiophenol Usage And Synthesis

Chemical Properties

clear colorless to light yellow liquid

Uses

It is used in the synthesis of Bicalutamide, an anti-cancer drug.

Definition

ChEBI: 4-Fluorothiophenol is a thiol.

Synthesis

The general procedure for the synthesis of p-fluorothiophenol from p-bromofluorobenzene is as follows: In a Schlenk tube, pre-dried in an oven, the aryl halide p-bromofluorobenzene (0.5 mmol), sodium thiosulphate (100 mg), cesium carbonate (1 mmol, 325 mg), an appropriate amount of tris(dibenzylideneacetone)dipalladium/palladium acetate, and Xphos ligands were added in turn to the tube and placed in a magnetic stirring chamber. Sub. The Schlenk tube was evacuated and replaced three times with argon, followed by the addition of an appropriate amount of solvent. The reaction mixture was stirred at room temperature until uniformly dispersed. Next, the reaction tube was placed in an oil bath at 80°C and stirred for 24 hours. Upon completion of the reaction, the solids were separated by filtration and washed with ether. Zinc powder (0.5 g) and 10% hydrochloric acid solution (5 mL) were added to the resulting solid under cooling conditions in an ice water bath. After stirring for 1 h, the reaction mixture was extracted with ethyl acetate. The organic layers were combined, washed sequentially with water and saturated saline and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the crude product of p-fluorothiophenol of satisfactory purity. For part of the relatively stable product, it can be further purified by column chromatography.

References

[1] Tetrahedron Letters, 2011, vol. 52, # 2, p. 205 - 208
[2] Chemische Berichte, 1939, vol. 72, p. 594
[3] Journal of the Chemical Society, 1962, p. 1062 - 1067

4-Fluorothiophenol(371-42-6)Related Product Information

• 4-Fluorobenzonitrile
• 4-Chlorothiophenol
• 4-Fluoronitrobenzene
• 4-Fluoroaniline
• 4-Bromofluorobenzene
• 4-Fluorophenol
• 4-Fluorophenylacetic acid
• 4-Fluorobenzaldehyde
• 4-Fluoromandelic acid
• Methyl 4-fluorobenzoate
• Ethyl 4-fluorobenzoate
• 4-Fluorobenzoic acid
• 4-Fluorobenzylamine
• 4-Fluorobenzamide
• 4-Fluorobenzoyl chloride
• 4-FLUOROTHIOANISOLE
• 4-Fluorobenzenesulfonamide
• Thiophenol