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Pentachlorobenzenethiol

From Wikipedia, the free encyclopedia
Pentachlorobenzenethiol
Names
Preferred IUPAC name
Pentachlorobenzenethiol
Other names
Pentachlorobenzenethiol, pentachlorothiophenol, PCBT
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.644 Edit this at Wikidata
EC Number
  • 205-107-8
UNII
  • InChI=1S/C6HCl5S/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
    Key: LLMLGZUZTFMXSA-UHFFFAOYSA-N
  • C1(=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)S
Properties
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)
Insoluble
Hazards
GHS labelling:
GHS05: Corrosive
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).

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

Synthesis

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Pentachlorobenzenethiol can be obtained from hexachlorobenzene.[3]

Properties

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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

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

See also

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References

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  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. 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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