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T32808 Sigma-Aldrich

Thiophenol

97%

Synonym: Benzenethiol, Phenyl mercaptan

  • CAS Number 108-98-5

  • Linear Formula C6H5SH

  • Molecular Weight 110.18

  •  Beilstein/REAXYS Number 506523

  •  EC Number 203-635-3

  •  MDL number MFCD00004826

  •  PubChem Substance ID 24900127

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, Chemical Synthesis, Chemicals for the synthesis of candidate COVID-19 treatments, Materials Science, Micro/NanoElectronics,
Quality Level   100
vapor density   3.8 (vs air)
vapor pressure   1.4 mmHg ( 20 °C)
assay   97%
refractive index   n20/D 1.588 (lit.)
bp   169 °C (lit.)
mp   −15 °C (lit.)
density   1.073 g/mL at 25 °C (lit.)
SMILES string   Sc1ccccc1
InChI   1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
InChI key   RMVRSNDYEFQCLF-UHFFFAOYSA-N

Description

Application

Thiophenol can undergo:
• Asymmetric Michael addition to diisopropyl maleate in the presence of a catalytic amount of cinchonine to form (s)-(−)-diisopropyl phenylthiosuccinate, which can be further converted to (R)-(+)-3,4-epoxy-1-butanol.
• Regioselective and stereoselective 1,4-addition to alkenylidenecyclopropanes leading to endo- or cis-vinyl sulfide adducts, a key step in the synthesis of karahanaenone.
• Diastereoselective addition to (S)-N-(α,β-unsaturated carbonyl)-γ-[(trityloxy)methyl]-γ-butyrolactams to form the corresponding β-(phenylthio)carboxylates.

Packaging

1 kg in Sure/Seal™

100, 500 g in Sure/Seal™

Safety & Documentation

Safety Information

Signal word 
Danger
Target organs 
Kidney, Respiratory system
RIDADR 
UN 2337 3(6.1) / PGI
WGK Germany 
WGK 3
RTECS 
DC0525000
Flash Point(F) 
122.0 °F - closed cup
Flash Point(C) 
50 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Meet Synthia - Retrosynthesis Sofware
Protocols & Articles

Articles

Micro and Nanometer Scale Photopatterning of Self-Assembled Monolayers

Graham J. Leggett* Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, United Kingdom *Email: Graham.Leggett@shef.ac.uk
Keywords: Absorption, Adsorption, Degradations, Deposition, Microscopy, Optical microscopy, Oxidations, Polymerization reactions, Semiconductor, Spectroscopy

Nicewicz Photoredox Catalysts for Anti-Markovnikov Alkene Hydrofunctionalization

While Markovnikov alkene reactivity is very well developed and utilized commonly in the synthesis of commodity and research chemicals, catalytic access to the anti-Markovnikov-selective adducts is a ...
Keywords: Catalysis, Cyclizations, Cycloadditions, Decarboxylations, Hydroaminations, Infrared spectroscopy, Oxidations

Peer-Reviewed Papers
15

References

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