CAS 100-68-5|thioanisole|Thioanisole 99%|(methylsulfanyl)benzene|METHYL PHENYL SULFIDE|茴香硫醚|Methyl phenyl sulfide|甲基苯基硫醚|THIOANISOLE|苯甲硫醚|Thioanisole|Methyl phenyl sulfide|茴香硫醚|甲基...

General Information

Structure

Molecular Formula

C₇H₈S

Molecular Mass

124.20342

Exact Mass

124.03467126

Charge

InChI

InChI=1S/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3

InChIKey

HNKJADCVZUBCPG-UHFFFAOYSA-N

Canonic Smiles

CSc1ccccc1

Isomeric Smiles

S(c1ccccc1)C

Calculated Properties

JChem

LogD (pH = 7.4)

2.60

LogD (pH = 5.5)

2.60

Log P

2.60

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Polar Surface Area

0.00

Polarizability

13.89

Molar Refractivity

38.82

LOG S

-2.11

Data Source

Names and Identifiers

IUPAC Traditional name

thioanisole

Synonyms

Thioanisole 99%METHYL PHENYL SULFIDE茴香硫醚Methyl phenyl sulfide甲基苯基硫醚THIOANISOLE苯甲硫醚ThioanisoleMethyl phenyl sulfide茴香硫醚甲基苯基硫醚thioanisolemethylthiobenzene(methylthio)benzenephenyl methyl sulfide1-phenyl-1-thiaethanemethyl phenyl thioethermethylphenylsulfidephenylthiomethane(1-thiaethyl)benzene

IUPAC name

(methylsulfanyl)benzene

Names and Identifiers

Registration numbers

MDL Number

MFCD00008559

Beilstein Number

1904179

PubChem SID

24900081248891022490190916206931485334057

EC Number

CAS Number

FEMA ID

Flavis Number

PubChem CID

BKMS React Database

164317433943879162805339044920622574616799

BRENDA Database

1.11.1.101.14.14.11.11.1.71.14.13.2431.14.13.841.14.14.111.14.13.921.14.13.81.14.12.111.14.13.2361.11.1.111.8.5.31.14.13.222.1.1.91.11.2.31.5.1.361.14.12.121.11.2.2

BRENDA Ligand Database

492061643174339339041628052257461679943879

Protein Data Bank

4hm8

MetaboLights Database

MTBLS2406MTBLS1642MTBLS1071

PubMed Citation Links

240920081112111321168267256822272305309521261073

SABIO-RK Database

CHEBI ID

MetaCyc Database

CompTox Database

NMRShiftDB Database

CHEMBL

Reaxys Registry

ACToR Database

PDBeChem Database

HMDB Database

SureChEMBL Database

Registration numbers

Properties

Related Proteins

PDB Bank

4HM8

Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

05216031

MP Biomedicals Rare Chemical collection

Sigma Aldrich

88470

Other Notes
Efficient promotor for the acid catalyzed cleavage of N-Z, O-benzyl and O-methyl protecting groups1,2,3

T28002

Packaging
25, 100, 500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

ChEBI

CHEBI:134281

An aryl sulfide that is thiophenol in which the hydrogen of the thiol group has been replaced by a methyl group.

Molecule Details

References

PubChem Literature

From Data Sources

• Monolithiation is thought to occur initially on the ring, but rearrangement then gives the more stable phenylthiomethyllithium: J. Org. Chem., 31, 4097 (1966); Tetrahedron Lett., 1961 (1977). Further metallation occurs at the ortho-position. See, e.g.: Tetrahedron, 46, 861 (1990). Demetallation and acylation is the basis of a route to 3-substituted benzo[b]thiophenes: Synthesis, 888 (1988):

• Cation scavenger in the acidic deprotection of peptides; see, e.g.: Int. J. Pept. Prot. Res., 36, 255 (1990). See Appendix 6. The combination of the soft nucleophile thioanisole and the hard acid triflic acid has been used for the cleavage of methyl ethers, e.g. O-methyltyrosine, resistant to other methods: J. Chem. Soc., Chem. Commun., 971 (1979). The same conditions have been used for the cleavage of Cbz, Boc, benzyl and 4-methoxybenzyl protecting groups in peptide synthesis: Chem. Pharm. Bull., 28, 1214 (1980); 29, 600 (1981); J. Chem. Soc., Chem. Commun., 101 (1980); see also: Angew. Chem. Int. Ed., 33, 1729 (1994).

References

Bioactivity

PubChem BioAssay

Bioactivity