Diphenyl diselenide

• Catalog No.: A13919
• CAS Number: 1666-13-3
• M. F.: C12H10Se2
• M. W.: 312.1278
• Purity: 98%

SYNONYMS

• Title: 二苯基二硒醚
• IUPAC name: (phenyldiselanyl)benzene
• IUPAC Traditional name: diphenyl diselenide
• Synonyms: Phenyl diselenide

DATABASE IDS

• CAS Number: 1666-13-3
• MDL Number: MFCD00003001
• Beilstein Number: 2047179
• EC Number: 216-780-2

PROPERTIES

• Purity: 98%
• Melting Point: 61-63°C
• GHS Hazard statements: H301-H331-H373-H400-H410
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P260-P261-P301+P310-P321-P405-P501A
• Risk Statements: 23/25-33-50/53
• RTECS: JM9152500
• Safety Statements: 20/21-28-45-60-61
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN3283
• Packing Group: II

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).