{[(phenylsulfanyl)methyl]sulfanyl}benzene

• ChemBase ID: 8582
• Molecular Formular: C13H12S2
• Molecular Mass: 232.36438
• Monoisotopic Mass: 232.03804238
• SMILES: c1(ccccc1)SCSc1ccccc1
• Canonical SMILES: C(Sc1ccccc1)Sc1ccccc1
• InChI: InChI=1S/C13H12S2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h1-10H,11H2
• InChIKey: ZHUPZVIALZHGGP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(phenylsulfanyl)methyl]sulfanyl}benzene
• IUPAC Traditional name: {[(phenylsulfanyl)methyl]sulfanyl}benzene
• Synonyms: Bis(phenylthio)methane; Formaldehyde diphenyl mercaptal; Diphenylthiomethane; Bis(phenylthio)methane; 1-{[(phenylthio)methyl]thio}benzene; Formaldehyde diphenyl mercapatal; 双(苯硫基)甲烷; 二苯硫基甲烷

Database IDs

• CAS Number: 3561-67-9
• EC Number: 222-624-4
• MDL Number: MFCD00003067
• Beilstein Number: 1874146
• PubChem SID: 160971889; 24871269
• PubChem CID: 77097

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.57298
• LogD (pH = 7.4): 4.57298
• Log P: 4.57298
• Molar Refractivity: 70.8579 cm^3
• Polarizability: 27.921627 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 34-37 °C(lit.); 34-37°C; 36-38°C; 36-38°C
• Boiling Point: 194 °C/8 mmHg(lit.); 194°C/8mm; 194°C/8mm
• Flash Point: 113 °C; 113°C; 235.4 °F

Safety Information

• Storage Warning: Irritant/Stench/Keep Cold; STENCH
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (GC); 97%; 98+%
• Linear Formula: CH2(SC6H5)2

DETAILS

Sigma Aldrich - 294586

Packaging
5 g in glass bottle

Sigma Aldrich - 47655

Other Notes
Acyl anion equivalent with some advantages over 1,3-dithiane;1,2 for the preparation of vinyl sulfides.3
Packaging
10 g in glass bottle

REFERENCES

• Acyl anion equivalent, compare 1,3-Dithiane, A10505. Can be metallated, e.g. with n-BuLi. Dimetallation requires a metal complexing agent, e.g. TMEDA, allowing dialkylation: Tetrahedron Lett., 21, 4763 (1980).
• The products of addition of the lithio-derivative to aldehydes and ketones undergo a pinacol-type rearrangement with CuOTf, with insertion of a one-carbon unit adjacent to the carbonyl group: J. Am. Chem. Soc., 97, 4749 (1975); see also: Org. Synth. Coll., 6, 737 (1988). An alternative method utilizes an alkyllithium to effect a carbenoid rearrangement, which has been applied to ring expansion: Tetrahedron Lett., 28, 20 (1987):