Pentachlorobenzenethiol

Pentachlorobenzenethiol is a chemical compound from the group of thiols and organochlorine compounds.^[1] The chemical formula is C
₆HCl
₅S.^[2]

Pentachlorobenzenethiol

Names
Preferred IUPAC name Pentachlorobenzenethiol
Other names Pentachlorobenzenethiol, pentachlorothiophenol, PCBT
Identifiers
CAS Number	133-49-3 Y
3D model (JSmol)	Interactive image
ChemSpider	8301
ECHA InfoCard	100.004.644
EC Number	205-107-8
PubChem CID	8620
UNII	92A1Z48VJB Y
CompTox Dashboard (EPA)	DTXSID3044540
InChI InChI=1S/C6HCl5S/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H Key: LLMLGZUZTFMXSA-UHFFFAOYSA-N
SMILES C1(=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)S
Properties
Chemical formula	C6HCl5S
Molar mass	282.38 g·mol−1
Appearance	Gray solid
Density	1.7±0.1 g/cm3
Melting point	231.5 °C (448.7 °F; 504.6 K)
Solubility in water	Insoluble
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Flash point	144.6 °C (292.3 °F; 417.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis

Pentachlorobenzenethiol can be obtained from hexachlorobenzene.^[3]

Properties

Pentachlorobenzenethiol is a combustible gray solid with an unpleasant odor, practically insoluble in water. It has a monoclinic crystal structure.^[4] The compound is not well-biodegradable and presumably bioaccumulable and toxic for aquatic organisms. Pentachlorobenzenethiol is itself a metabolite of hexachlorobenzene and is found in the urine and the excretions of animals receiving hexachlorobenzene.^[5] Pentachlorobenzenethiol has a high potential for long-range transport via air as it is very slowly degraded in atmosphere.^[6]

Applications

Pentachlorobenzenethiol is used in the rubber industry. The compound is added to rubber (both natural and synthetic) to facilitate processing (mastication).