thiophenol

CAS No. 108-98-5

Formula: C6H6S
Basic Info

Thiophenol is an organosulfur compound with the formula C6H5SH, sometimes abbreviated as PhSH. This foul-smelling colourless liquid is the simplest 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, in the case of 'thiol' that the alcohol 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 the medicine thiomersal is a thiophenol.

Formula
C6H6S
Molecular Weight
110.177
Exact Mass
110.019
LogP
1.9753
PSA
38.8
Synonyms

phenyl mercaptan

Benzenethiol

benzene-thiol

thio-pheno

2-mercaptobenzene

Benzolthiol

Thiohenol

Thiophenol

FEMA 3616

Thiofenol

phenylthiol

USAF XR-19

mercaptobenzene

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Properties
Appearance & Physical State
clear liquid with a repulsive odor
Density
1.078
Boiling Point
167-169ºC
Melting Point
-15ºC
Flash Point
50ºC
Refractive Index
1.588-1.59
Water Solubility
insoluble
Stability
Stable. Flammable. May form explosive mixtures with air. Stench. Incompatible with strong oxidizing agents.
Storage Condition
Store at RT.
Vapor Density
3.8 (vs air)
Vapor Pressure
1.4 mm Hg ( 20 °C)
Safety Info
RTECS
DC0525000
Safety Statements
S16-S26-S28-S36/37/39-S45
WGK Germany
3
Risk Statements
R10; R24/25; R26; R36/37/38
HS Code
2930909090
RIDADR
UN 2337
Hazard Class
6.1
Packing Group
I
Caution Statement
P210; P280; P302 + P352 + P310; P304 + P340 + P310; P370 + P378
Hazard Codes
Spectrum
NMR Spectrum 1H NMR : 90 MHz in CDCl3
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IR Spectrum IR : liquid film
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Mass Spectrum Mass spectrum (electron ionization)
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Analysis Methods
Kovats' RI, non-polar column, isothermal
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Column Shape
Packed
Active Phase(℃)
Apiezon M
Retention index
999.
Temperature Control
130.
Method
isothermal
Comments
He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m
Reference
Garbuzov, V.G.Misharina, T.A.Aerov, A.F.Golovnya, R.V.Gas chromatographic retention indices for sulphur(II)-containing organic substancesJ. Anal. Chem. USSR (Engl. Transl.)1985, 40, 4, 576-586.
Kovats' RI, non-polar column, isothermal
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Column Shape
Packed
Active Phase(℃)
Apiezon M
Retention index
999.
Temperature Control
130.
Method
isothermal
Comments
Chromosorb W, AW/DMS; Column length: 2.1 m
Reference
Golovnya, R.V.Garbuzov, V.G.Aerov, A.F.Gas chromatographic characterization of sulfur-containing compounds. 5. Thiophene, furan, and benzene derivativesIzv. Akad. Nauk SSSR Ser. Khim.1978, 11, 2271-2274.
Kovats' RI, non-polar column, isothermal
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Column Shape
Capillary
Active Phase(℃)
Squalane
Retention index
942.
Temperature Control
120.
Method
isothermal
Comments
N2, Celite 545; Column length: 50. m; Column diameter: 0.3 mm
Reference
Agrawal, B.B.Tesarík, K.Janák, J.Gas chromatographic characterization of sulphur compounds in the 93-162° gasoline cut from Romashkino crude oil using Kováts retention indicesJ. Chromatogr.1972, 65, 1, 207-215.
Kovats' RI, non-polar column, isothermal
expand collapse
Column Shape
Capillary
Active Phase(℃)
Squalane
Retention index
933.
Temperature Control
86.
Method
isothermal
Comments
N2, Celite 545; Column length: 50. m; Column diameter: 0.3 mm
Reference
Agrawal, B.B.Tesarík, K.Janák, J.Gas chromatographic characterization of sulphur compounds in the 93-162° gasoline cut from Romashkino crude oil using Kováts retention indicesJ. Chromatogr.1972, 65, 1, 207-215.
Kovats' RI, non-polar column, isothermal
expand collapse
Column Shape
Capillary
Active Phase(℃)
Apiezon L
Retention index
966.
Temperature Control
120.
Method
isothermal
Comments
N2; Column length: 100. m; Column diameter: 0.3 mm
Reference
Agrawal, B.B.Tesarík, K.Janák, J.Gas chromatographic characterization of sulphur compounds in the 93-162° gasoline cut from Romashkino crude oil using Kováts retention indicesJ. Chromatogr.1972, 65, 1, 207-215.

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