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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:30:22 UTC
Update Date2017-12-07 03:27:57 UTC
HMDB IDHMDB0033746
Secondary Accession Numbers
  • HMDB33746
Metabolite Identification
Common NameBenzenethiol
DescriptionBenzenethiol is a flavouring agent Thiophenol is a chemical compound with the formula C6H5SH, and sometimes abbreviated as PhSH. The foul-smelling liquid is the principal aromatic thiol. The chemical structures of thiophenols are analogous to phenols except the oxygen atom in the hydroxyl group (-OH) bonded to the aromatic ring is replaced by a sulfur atom. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, thio- commonly means that the oxygen atom is replaced by a sulfur atom. Thiophenols also describes a class of compounds formally derived from thiophenol itself. All have a sulfhydryl group (-SH) covalently bonded to an aromatic ring. The organosulfur ligand in medicine merthiolate is a thiophenol.
Structure
Thumb
Synonyms
ValueSource
MercaptobenzeneChEBI
Phenyl mercaptanChEBI
PhenylthiolChEBI
FEMA 3616HMDB
mercapto-BenzeneHMDB
PhenylmercaptanHMDB
Sodium benzenethiolateHMDB
thio-PhenolHMDB
ThiofenolHMDB
ThiophenateHMDB
ThiophenolHMDB
Thiophenol, potassium saltMeSH
Thiophenol, sodium saltMeSH
Thiophenol, copper (+1) saltMeSH
Chemical FormulaC6H6S
Average Molecular Weight110.177
Monoisotopic Molecular Weight110.019020882
IUPAC Namebenzenethiol
Traditional Namethiophenol
CAS Registry Number108-98-5
SMILES
SC1=CC=CC=C1
InChI Identifier
InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
InChI KeyRMVRSNDYEFQCLF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thiophenols. These are compounds containing a thiophenol ring, which a phenol derivative obtained by replacing the oxygen atom from the hydroxyl group (attached to the benzene) by a sulfur atom.
KingdomOrganic compounds
Super ClassBenzenoids
ClassThiophenols
Sub ClassNot Available
Direct ParentThiophenols
Alternative Parents
Substituents
  • Thiophenol
  • Monocyclic benzene moiety
  • Arylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-14.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.84 mg/mL at 25 °CNot Available
LogP2.52Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.17 g/LALOGPS
logP2.26ALOGPS
logP2.07ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)6.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.07 m³·mol⁻¹ChemAxon
Polarizability11.93 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-f00b12d067160b203ec9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-9400000000-963c74e11e0fee28cdedView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-8900000000-f00b12d067160b203ec9View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03xr-9400000000-963c74e11e0fee28cdedView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9500000000-39461b1b5833a05c75b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-902e432c58a5b48af6d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-d103552d249a6486076cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-73bb0429feae5d758aafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-08819ed59079e9d5777aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-cf3fe95c00ee01bcc740View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3900000000-0744499c38c462f82335View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011878
KNApSAcK IDNot Available
Chemspider ID7681
KEGG Compound IDNot Available
BioCyc IDCPD-8132
BiGG IDNot Available
Wikipedia LinkThiophenol
METLIN IDNot Available
PubChem Compound7969
PDB IDBT6
ChEBI ID48498
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barrese AA 3rd, Genis C, Fisher SZ, Orwenyo JN, Kumara MT, Dutta SK, Phillips E, Kiddle JJ, Tu C, Silverman DN, Govindasamy L, Agbandje-McKenna M, McKenna R, Tripp BC: Inhibition of carbonic anhydrase II by thioxolone: a mechanistic and structural study. Biochemistry. 2008 Mar 11;47(10):3174-84. doi: 10.1021/bi702385k. Epub 2008 Feb 12. [PubMed:18266323 ]
  2. Patil G, Rudolph R, Lange C: In vitro-refolding of a single-chain Fv fragment in the presence of heteroaromatic thiols. J Biotechnol. 2008 Apr 30;134(3-4):218-21. doi: 10.1016/j.jbiotec.2008.01.009. Epub 2008 Jan 18. [PubMed:18321603 ]
  3. Park G, Lee KG, Lee SJ, Park TJ, Wi R, Wang KW, Kim DH: Ultrasound-aided formation of gold nanoparticles on multi-walled carbon nanotubes functionalized with mercaptobenzene moieties. J Nanosci Nanotechnol. 2011 Jul;11(7):6222-6. [PubMed:22121689 ]
  4. Montanari L, Pavanetto F, Modena T, Mazza M: [Antifungal activity of diesters of 2-mercaptobenzene methanethiol]. Farmaco Sci. 1982 Nov;37(11):759-63. [PubMed:7152011 ]
  5. SCHNITZER RJ, KELLY DR, SOO-HOO G, GRUNBERG E, UNGER C: Chemotherapeutic studies on a new stibonic acid, 2-carboxymethyl-mercaptobenzene stibonic acid, Ro 2-1160. Arch Int Pharmacodyn Ther. 1951 Jan;85(1-2):100-11. [PubMed:14820391 ]
  6. Harnisch JA, Pris AD, Porter MD: Attachment of gold nanoparticles to glassy carbon electrodes via a mercaptobenzene film. J Am Chem Soc. 2001 Jun 20;123(24):5829-30. [PubMed:11403628 ]
  7. WAGNER G, LENK C: [On the preparation and properties of amino-mercaptobenzene-N,S-bis-glycosides]. Arch Pharm. 1962 Jun;295/67:415-27. [PubMed:14004344 ]
  8. Hochalter JB, Wattenberg LW, Coccia JB, Galbraith AR: Inhibition of beta-propiolactone-induced neoplasia of the forestomach and large bowel by 4-mercaptobenzene sulfonate in mice and rats. Cancer Res. 1988 May 15;48(10):2740-3. [PubMed:3359434 ]
  9. Mirek J, Chojnacka-Wojcik E, Tatarzynska E, Wiczynska B: Synthesis of 3-phenyl-3-phenylthiopropionic acids, amides, amines and studies on their pharmacological properties. Farmaco Sci. 1985 Sep;40(9):701-8. [PubMed:4076432 ]
  10. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .