(phenyldisulfanyl)benzene

• ChemBase ID: 7877
• Molecular Formular: C12H10S2
• Molecular Mass: 218.3378
• Monoisotopic Mass: 218.02239232
• SMILES: S(Sc1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)SSc1ccccc1
• InChI: InChI=1S/C12H10S2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
• InChIKey: GUUVPOWQJOLRAS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (phenyldisulfanyl)benzene
• IUPAC Traditional name: diphenyl disulfide
• Synonyms: Diphenyl disulfide; Phenyl disulfide; Diphenyl disulfide; PHENYL DISULFIDE; Phenyl disulfide; Diphenyl disulfide; Diphenyl disulphide; 二硫化二苯; 二苯二硫醚; 二苯基二硫; 二苯基二硫醚

Database IDs

• CAS Number: 882-33-7
• EC Number: 212-926-4
• MDL Number: MFCD00003065
• Beilstein Number: 639794
• PubChem SID: 24850260; 24901566; 160971184; 24866872
• PubChem CID: 13436
• CHEMBL: 462861
• Chemspider ID: 12861
• FEMA ID: 3225
• Wikipedia Title: Diphenyl_disulfide
• Council of Europe Number: 11757
• Flavis Number: 12.043

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.573745
• LogD (pH = 7.4): 4.573745
• Log P: 4.573745
• Molar Refractivity: 62.4602 cm^3
• Polarizability: 26.08982 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Diethyl ether,; Benzene,; Carbon disulfide,; THF; Insoluble in water
• Apperance: Colourless crystals
• Melting Point: 58-60 °C; 58-60 °C(lit.); 58-60°C; 58-62°C; 61–62 °C
• Boiling Point: 310°C
• Density: ? g/cm^3; 1.353
• Organoleptic: earthy; sulfurous

Safety Information

• Storage Warning: Irritant; IRRITANT, STENCH
• RTECS: SS6825000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: true; 是
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• Main Hazard: Flammable
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H400
• GHS Precautionary statements: P261-P273-P305 + P351 + P338; P280G-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥97.0% (HPLC); ≥98%; 98%; 99%
• Grade: Halal; Kosher; technical
• Linear Formula: C6H5SSC6H5

DETAILS

MP Biomedicals - 05221891

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 169021

Packaging
10, 50, 250 g in poly bottle

Sigma Aldrich - W322504

Packaging
1 kg in glass bottle
100 g in glass bottle

Sigma Aldrich - 42960

Other Notes
Reagent for the α-phenylsulfenylation of carbonyl compounds1

REFERENCES

• Also sulfenylates organolithium reagents from, e.g. lithiated furans: J. Org. Chem., 46, 2473 (1981).
• Sulfenylation agent for enolates of ketones, esters or carboxylic acid dianions: J. Am. Chem. Soc., 95, 6840 (1973); 98, 4887 (1976); Chem. Rev., 78, 363 (1978). Oxidation to the sulfoxide and thermal elimination can be used for the conversion of ketones to enones via thermal sulfoxide elimination, less frequently used than the selenoxide route (cf preceding entry), due to the higher temperatures required.
• Alkyl halides under phase-transfer conditions give alkyl phenyl sulfides in good yields,: Synth. Commun., 12, 595 (1982), and alkenyl halides in the presence of CuI give alkenyl sulfides: Chem. Lett., 769 (1989).
• For use as a catalyst in the photochemical cis-trans isomerization of olefins (used in the synthesis of the macrolide ricinelaidic acid lactone), see: Org. Synth. Coll., 7, 470 (1990).