CAS 108-98-5|Thiophenol|硫酚|benzenethiol|苯硫酚|硫酚|Benzenethiol|Thiophenol|Benzenethiol|巯基苯|苯硫酚|Phenyl mercaptan|thiophenol|Thiophenol 99%|Phenyl mecaptan|Thiophenol|Phenylthiol|mercaptoben...

General Information

Structure

Molecular Formula

C₆H₆S

Molecular Mass

110.17684

Exact Mass

110.01902119

Charge

InChI

InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H

InChIKey

RMVRSNDYEFQCLF-UHFFFAOYSA-N

Canonic Smiles

Sc1ccccc1

Isomeric Smiles

Sc1ccccc1

Calculated Properties

JChem

LogD (pH = 7.4)

1.32

LogD (pH = 5.5)

2.04

Log P

2.07

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

6.64

Polar Surface Area

0.00

Polarizability

11.93

Molar Refractivity

34.07

LOG S

-1.97

Data Source

Names and Identifiers

Synonyms

Thiophenol硫酚苯硫酚硫酚BenzenethiolThiophenolBenzenethiol巯基苯苯硫酚Phenyl mercaptanThiophenol 99%Phenyl mecaptanThiophenolPhenylthiolmercaptobenzenethiophenolphenyl mercaptan

IUPAC name

benzenethiol

IUPAC Traditional name

thiophenol

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

Wikipedia Title

CHEMBL

Chemspider ID

Unique Ingredient Identifier

CHEBI ID

MDL Number

FEMA ID

Flavis Number

Council of Europe Number

11585

Merck Index

149355

PubChem SID

2490181124846302249001272485441116204023749693626

EC Number

203-635-3

Beilstein Number

506523

BKMS React Database

1367469818384013916016288030342115320

BRENDA Ligand Database

8401362880981833034291601115320136746

PubMed Citation Links

2390200423961762

Protein Data Bank

3hsr7a0z

Patent number

EP1179530EP1466911US2002058660WO2005005432US2006116422EP0895991WO2006117762EP1707188EP0972770US2003175848WO2006025859WO2008129562US2005043401US2007203192

BRENDA Database

1.14.13.71.13.12.163.1.1.12.4.1.173.1.1.532.5.1.484.4.1.94.5.1.53.5.1.884.1.99.22.1.1.93.1.1.473.2.1.1471.1.1.14.4.1.15

ACToR Database

NMRShiftDB Database

CompTox Database

MetaCyc Database

Reaxys Registry

SureChEMBL Database

MetaboLights Database

MTBLS2224

HMDB Database

HMDB0033746

Registration numbers

Properties

Safety Information

Very Toxic/Flammable

Air Sensitive

R10 24/25 26 41

10-24/25-26-41

Pharmacology Properties

no known allergens

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Wikipedia

Thiophenol

Sigma Aldrich

240249

Packaging
10 g in glass bottle
50 g in Sure/Seal™
Application
Used in the preparation of β-lactones.1
Protocols & Applications
The Progress in Development of Dental Restorative Materials

T32808

Packaging
1 kg in Sure/Seal™
100, 500 g in Sure/Seal™

W361607

Packaging
1 kg in glass bottle
1 sample in glass bottle

ChEBI

CHEBI:48498

A thiol in which the sulfanyl group is attached to a phenyl group.

Molecule Details

References

PubChem Literature

From Data Sources

• Interception of the DMF adduct provides a source of the unstable 2-mercaptobenzaldehyde. Alternatively, ortho-metallated thiophenols can be formed by lithiation of the THP ether, in which coordination by oxygen favors ortho-lithiation: J. Am. Chem. Soc., 111, 658 (1989).

• Chlorination of PhSH with NCS: J. Org. Chem., 37, 1367 (1972), or SO₂Cl₂: Org. Synth. Coll., 8, 550 (1993), gives the useful reagent benzenesulfenyl chloride, PhSCl.

• For a detailed investigation of alkylation using, e.g. K₂CO₃ in acetone, see: Synth. Commun., 22, 1691 (1992). Unactivated aryl chlorides undergo nucleophilic substitution in the presence of K₂CO₃ in NMP to give aryl sulfides: J. Org. Chem., 56, 862 (1991).

• Dilithiation of PhSH with n-BuLi and TMEDA gives exclusive ortho-metallation: J. Am. Chem. Soc., 111, 654, 665, 2327 (1989). Subsequent treatment of the dilithio species with DMF, followed by in situ reaction with chloroacetone provides a useful route to the benzo[b]thiophene system: J. Org. Chem., 58, 1293 (1993):

• Michael additions occur readily with electron deficient alkenes. Subsequent chlorination with NCS and dehydrochlorination provides a stereoselective route to vinyl thioethers: J. Org. Chem., 46, 235 (1981):

• The Cu(I) derivative, phenylthiocopper forms complexes with alkyllithiums, which are useful alkyl transfer reagents, undergoing conjugate addition to enones, coupling with alkyl iodides to alkanes, and converting acid halides to ketones: J. Am. Chem. Soc., 95, 7788 (1973); Synthesis, 662 (1974); Org. Synth. Coll., 6, 248 (1988).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

Thiophenol硫酚苯硫酚硫酚BenzenethiolThiophenolBenzenethiol巯基苯苯硫酚Phenyl mercaptanThiophenol 99%Phenyl mecaptanThiophenolPhenylthiolmercaptobenzenethiophenolphenyl mercaptan

IUPAC name

benzenethiol

IUPAC Traditional name

thiophenol

Molecule Details

Wikipedia

Thiophenol

Sigma Aldrich

240249

Packaging
10 g in glass bottle
50 g in Sure/Seal™
Application
Used in the preparation of β-lactones.1
Protocols & Applications
The Progress in Development of Dental Restorative Materials

T32808

Packaging
1 kg in Sure/Seal™
100, 500 g in Sure/Seal™

W361607

Packaging
1 kg in glass bottle
1 sample in glass bottle

ChEBI

CHEBI:48498

A thiol in which the sulfanyl group is attached to a phenyl group.

References

PubChem Literature

From Data Sources

• Chlorination of PhSH with NCS: J. Org. Chem., 37, 1367 (1972), or SO₂Cl₂: Org. Synth. Coll., 8, 550 (1993), gives the useful reagent benzenesulfenyl chloride, PhSCl.