Skip to Content
Merck
All Photos(1)

Documents

T32808

Sigma-Aldrich

Thiophenol

97%

Synonym(s):

Benzenethiol, Phenyl mercaptan

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
C6H5SH
CAS Number:
108-98-5
Molecular Weight:
110.18
Beilstein:
506523
EC Number:
203-635-3
MDL number:
MFCD00004826
UNSPSC Code:
12352100
PubChem Substance ID:
24900127
NACRES:
NA.22

vapor density

3.8 (vs air)

Quality Level

100

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

Looking for similar products? Visit Product Comparison Guide

General description

Thiophenol is an organosulfur compound used as an intermediate to produce polymers.

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.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 3 - Repr. 2 - Skin Irrit. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

122.0 °F - closed cup

Flash Point(C)

50 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Thiophenol additions to alkenylidenecyclopropanes. A novel synthesis of karahanaenone.
Cairns P M, et al.
Tetrahedron Letters, 23(13), 1405-1408 (1982)
Palladium-Catalyzed Regioselective Addition of Thiophenol to Conjugated Enynes. Efficient Syntheses of 2-(Phenylsulfinyl) and 2-(Phenylsulfonyl) 1, 3-Dienes.
Baeckvall J-E and Anna E
The Journal of Organic Chemistry, 59(20), 5850-5851 (1994)
A ratiometric fluorescent probe for selective detection of thiophenol derivatives
Li F, et al.
Spectrochimica Acta Part A: Molecular Spectroscopy, 271, 120870-120870 (2022)
Diastereoselective Thiophenol Addition to (S)-N-. alpha.,. beta.-Unsaturated carbonyl-. gamma.-[(trityloxy) methyl]-. gamma.-butyrolactams.
Tomioka K, et al.
The Journal of Organic Chemistry, 60(19), 6188-6190 (1995)
Ki-Jeong Kim et al.
Scientific reports, 10(1), 2119-2119 (2020-02-09)
The surface morphology and electronic structure of hexagonal graphene onion rings (HGORs), a modified graphene structure, were investigated to confirm the possibility as an efficient catalyst when compared to graphene. After confirming the formation of HGORs with a smaller width
View All Related Papers

Articles

Nicewicz Photoredox Catalysts for Anti-Markovnik

Markovnikov and anti-Markovnikov alkene reactivity differences are discussed, highlighting challenges and catalytic advancements.

Nicewicz Photoredox Catalysts for Anti-Markovnik

Markovnikov and anti-Markovnikov alkene reactivity differences are discussed, highlighting challenges and catalytic advancements.

Nicewicz Photoredox Catalysts for Anti-Markovnik

Markovnikov and anti-Markovnikov alkene reactivity differences are discussed, highlighting challenges and catalytic advancements.

Nicewicz Photoredox Catalysts for Anti-Markovnik

Markovnikov and anti-Markovnikov alkene reactivity differences are discussed, highlighting challenges and catalytic advancements.

See All

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service