(phenyldiselanyl)benzene

• ChemBase ID: 123413
• Molecular Formular: C12H10Se2
• Molecular Mass: 312.1278
• Monoisotopic Mass: 313.91129232
• SMILES: [Se]([Se]c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)[Se][Se]c1ccccc1
• InChI: InChI=1S/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
• InChIKey: YWWZCHLUQSHMCL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (phenyldiselanyl)benzene
• IUPAC Traditional name: diphenyl diselenide
• Synonyms: 1,2-diphenyldiselane; Phenyl diselenide; Diphenyl diselenide; Diphenyl diselenide; 二苯联硒; 二苯基二硒醚

Database IDs

• CAS Number: 1666-13-3
• EC Number: 216-780-2
• MDL Number: MFCD00003001
• Beilstein Number: 2047179
• PubChem SID: 162217766; 24850881
• PubChem CID: 15460
• Chemspider ID: 14710
• Wikipedia Title: Diphenyl_diselenide

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.499
• LogD (pH = 7.4): 3.499
• Log P: 3.499
• Molar Refractivity: 77.1784 cm^3
• Polarizability: 19.828264 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Insoluble in water
• Apperance: Orange powder
• Melting Point: 59-61 °C; 59-61 °C(lit.); 60-63 °C; 61-63°C
• Density: 1.84 g/cm^3

Safety Information

• RTECS: JM9152500
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 3283; UN3283
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 23/25-33-50/53; R23/25 R33 R50/53
• Safety Statements: 20/21-28-45-60-61; S20/21 S28 S45 S60 S61
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• Main Hazard: Toxic
• GHS Hazard statements: H301-H331-H373-H400-H410; H301-H331-H373-H410
• GHS Precautionary statements: P260-P261-P301+P310-P321-P405-P501A; P261-P273-P301 + P310-P311-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3283 6.1/PG 2

Product Information

• Purity: ≥97.0% (GC); 95+%; 97%; 98%
• Grade: purum
• Impurities: <2% diphenyl selenide
• Linear Formula: C6H5SeSeC6H5

DETAILS

Sigma Aldrich - 180629

Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 42944

Other Notes
Reagent for introducing the phenylselenyl group, used for elimination and oxidation reactions, review1

REFERENCES

• Reagent for ɑ-phenylselenation of enolates. The products are readily oxidized to the selenoxides which undergo ambient temperature Cope-type elimination, providing a mild method for the introduction of ɑ?-unsaturation into, e.g. ketones: J. Am. Chem. Soc., 97, 5434 (1975):
  
• For a comprehensive review of the preparation of ɑ?-unsaturated carbonyl compounds and nitriles by selenoxide elimination, see: Org. React., 44, 1 (1993). Compare also Phenylselenenyl bromide, A11906 and Phenylselenenyl chloride, A12751.
• Oxidation of diphenyl diselenide by persulfate in the absence of a nucleophilic counter-ion generates the phenylselenium cation, which adds to alkenes. Molecules with a suitably placed nucleophilic site (alkene, hydroxyl, carbonyl, carboxyl, etc.) can then undergo intramolecular cyclization: J. Org. Chem., 55, 429 (1990); J. Chem. Soc. Perkin 1, 1989 (1993); Synlett, 373 (1994):
  
• For reviews of the application of organoselenium reagents in organic synthesis, see: Tetrahedron, 34, 1049 (1978); Acc. Chem. Res., 12, 22 (1979); 17, 28 (1984). Monograph: Organoselenium Chemistry, D. Liotta, ed., Wiley, N.Y. (1987).
• For introduction of the phenylseleno group by Michael addition, phenylselenol can be generated in situ by borohydride cleavage: Synthesis, 664 (1980).