View source for Chemistry:Pentachlorobenzenethiol

{{Chembox
<!-- Images -->
| ImageFile = Pentachlorbenzolthiol.svg
| ImageSize = 200px
| ImageAlt =
<!-- Names -->
| PIN = Pentachlorobenzenethiol
| OtherNames = Pentachlorobenzenethiol, pentachlorothiophenol, PCBT
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo = 133-49-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 92A1Z48VJB
| PubChem = 8620
| ChemSpiderID = 8301
| EINECS = 205-107-8
| SMILES = C1(=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)S
| StdInChI= 1S/C6HCl5S/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
| StdInChIKey= LLMLGZUZTFMXSA-UHFFFAOYSA-N
  }}
| Section2 = {{Chembox Properties
| C=6|H=1|Cl=5|S=1
| Appearance = Gray solid
| Density = 1.7±0.1 g/cm<sup>3</sup>
| Solubility = Insoluble 
| MeltingPtC = 231.5
| BoilingPtC = 
| VaporPressure = 
  }}
| Section3 = {{Chembox Hazards
| MainHazards = 
| GHSPictograms = {{GHS05}}
| GHSSignalWord = WARNING
| HPhrases = 
| PPhrases = 
| FlashPtC = 144.6 
| AutoignitionPt =
  }}
}}

'''Pentachlorobenzenethiol''' is a chemical compound from the group of thiols and organochlorine compounds.<ref>{{cite web|title=Pentachlorobenzenethiol|url=http://www.chemindustry.com/chemicals/0268505.html|publisher=chemindustry.com|accessdate=9 June 2017}}</ref> The chemical formula is {{chem|C|6|H|Cl|5|S}}.<ref>{{cite web|title=2,3,4,5,6-pentachlorobenzenethiol|url=http://www.chemsynthesis.com/base/chemical-structure-23939.html|accessdate=9 June 2017}}</ref>

==Synthesis==
Pentachlorobenzenethiol can be obtained from [[Chemistry:Hexachlorobenzene|hexachlorobenzene]].<ref>{{cite journal|last1=Kulka|first1=Marshall|title=Reaction of Hexachlorobenzene with Mercaptides|journal=J. Org. Chem.|date=1959|volume=24|issue=4|pages=235–237|doi=10.1021/jo01084a021}}</ref>

==Properties==
Pentachlorobenzenethiol is a combustible gray solid with an unpleasant odor, practically insoluble in water. It has a monoclinic crystal structure.<ref>{{cite journal|last1=Wojcik|first1=G.|last2=Charbonneau|first2=G. P.|last3=Delugeard|first3=Y.|last4=Toupet|first4=L.|title=The disordered crystal structure of pentachlorothiophenol|journal=Acta Crystallogr.|date=1980|volume=B36|issue=2|pages=506–507|doi=10.1107/S0567740880003706}}</ref> 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.<ref>{{cite journal|last1=Koss|first1=G.|last2=Koransky|first2=W.|last3=Steinbach|first3=K.|title=Studies on the toxicology of hexachlorobenzene: II. Identification and determination of metabolites.|journal=Archives of Toxicology|date=June 1976|volume=35|issue=2|pages=107–114|doi=10.1007/BF00372764|pmid=947309|s2cid=25403466 }}</ref> Pentachlorobenzenethiol has a high potential for long-range transport via air as it is very slowly degraded in atmosphere.<ref>{{cite web|title=TC NES SUBGROUP ON IDENTIFICATION OF PBT AND VPVB SUBSTANCES|url=https://echa.europa.eu/documents/10162/be8c1c49-af6e-4b6f-9927-b4e1bc7f50f5|website=EChA|publisher=echa.europa.eu|accessdate=9 June 2017}}</ref>

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

==See also==
*[[Chemistry:Chlorobenzene|Chlorobenzene]]
*[[Chemistry:Dichlorobenzene|Dichlorobenzene]]
*[[Chemistry:Trichlorobenzene|Trichlorobenzene]]
*[[Chemistry:Pentachlorobenzene|Pentachlorobenzene]]
*[[Chemistry:Hexachlorobenzene|Hexachlorobenzene]]

==References==
{{Reflist}}

==External links==
*[https://www.google.ch/patents/US2922820 Preparation of pentachlorothiophenol US 2922820 A]

[[Category:Benzene derivatives]]
[[Category:Thiols]]
[[Category:Organochlorides]]
[[Category:Foul-smelling chemicals]]

{{Sourceattribution|Pentachlorobenzenethiol}}