Pentachlorobenzenethiol
{{Chembox
| ImageFile = Pentachlorbenzolthiol.svg
| ImageSize = 200px
| ImageAlt =
| PIN = Pentachlorobenzenethiol
| OtherNames = Pentachlorobenzenethiol, pentachlorothiophenol, PCBT
| 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/cm3
| 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.{{cite web|title=Pentachlorobenzenethiol|url=http://www.chemindustry.com/chemicals/0268505.html|publisher=chemindustry.com|accessdate=9 June 2017}} The chemical formula is {{chem|C|6|H|Cl|5|S}}.{{cite web|title=2,3,4,5,6-pentachlorobenzenethiol|url=http://www.chemsynthesis.com/base/chemical-structure-23939.html|accessdate=9 June 2017}}
Synthesis
Properties
Pentachlorobenzenethiol is a combustible gray solid with an unpleasant odor, practically insoluble in water. It has a monoclinic crystal structure.{{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|bibcode=1980AcCrB..36..506W }} 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.{{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|bibcode=1976ArTox..35..107K |s2cid=25403466 }} Pentachlorobenzenethiol has a high potential for long-range transport via air as it is very slowly degraded in atmosphere.{{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}}
Applications
Pentachlorobenzenethiol is used in the rubber industry. The compound is added to rubber (both natural and synthetic) to facilitate processing (mastication).
See also
References
{{Reflist}}
External links
- [https://www.google.ch/patents/US2922820 Preparation of pentachlorothiophenol US 2922820 A]