Pentachlorobenzenethiol

Pentachlorobenzenethiol
Names
	Preferred IUPAC name Pentachlorobenzenethiol
	Other names Pentachlorobenzenethiol, pentachlorothiophenol, PCBT
Identifiers
CAS Number	133-49-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	8301;
ECHA InfoCard	100.004.644
EC Number	205-107-8;
PubChem CID	8620;
UNII	92A1Z48VJB ;
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

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

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).

References

^ "Pentachlorobenzenethiol". chemindustry.com. Retrieved 9 June 2017.
^ "2,3,4,5,6-pentachlorobenzenethiol". Retrieved 9 June 2017.
^ Kulka, Marshall (1959). "Reaction of Hexachlorobenzene with Mercaptides". J. Org. Chem. 24 (4): 235–237. doi:10.1021/jo01084a021.
^ Wojcik, G.; Charbonneau, G. P.; Delugeard, Y.; Toupet, L. (1980). "The disordered crystal structure of pentachlorothiophenol". Acta Crystallogr. B36 (2): 506–507. Bibcode:1980AcCrB..36..506W. doi:10.1107/S0567740880003706.
^ Koss, G.; Koransky, W.; Steinbach, K. (June 1976). "Studies on the toxicology of hexachlorobenzene: II. Identification and determination of metabolites". Archives of Toxicology. 35 (2): 107–114. Bibcode:1976ArTox..35..107K. doi:10.1007/BF00372764. PMID 947309. S2CID 25403466.
^ "TC NES SUBGROUP ON IDENTIFICATION OF PBT AND VPVB SUBSTANCES". EChA. echa.europa.eu. Retrieved 9 June 2017.

External links

Preparation of pentachlorothiophenol US 2922820 A

[1] "Pentachlorobenzenethiol". chemindustry.com. Retrieved 9 June 2017.

[2] "2,3,4,5,6-pentachlorobenzenethiol". Retrieved 9 June 2017.

[3] Kulka, Marshall (1959). "Reaction of Hexachlorobenzene with Mercaptides". J. Org. Chem. 24 (4): 235–237. doi:10.1021/jo01084a021.

[4] Wojcik, G.; Charbonneau, G. P.; Delugeard, Y.; Toupet, L. (1980). "The disordered crystal structure of pentachlorothiophenol". Acta Crystallogr. B36 (2): 506–507. Bibcode:1980AcCrB..36..506W. doi:10.1107/S0567740880003706.

[5] Koss, G.; Koransky, W.; Steinbach, K. (June 1976). "Studies on the toxicology of hexachlorobenzene: II. Identification and determination of metabolites". Archives of Toxicology. 35 (2): 107–114. Bibcode:1976ArTox..35..107K. doi:10.1007/BF00372764. PMID 947309. S2CID 25403466.

[6] "TC NES SUBGROUP ON IDENTIFICATION OF PBT AND VPVB SUBSTANCES". EChA. echa.europa.eu. Retrieved 9 June 2017.

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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