Phenylselenenyl chloride

• Catalog No.: A12751
• CAS Number: 5707-04-0
• M. F.: C6H5ClSe
• M. W.: 191.5169
• Purity: 98%

SYNONYMS

• Title: 苯基氯化硒
• IUPAC name: (chloroselanyl)benzene
• IUPAC Traditional name: (chloroselanyl)benzene
• Synonyms: Benzeneselenenyl chloride

DATABASE IDS

• EC Number: 227-196-2
• MDL Number: MFCD00000478
• Beilstein Number: 1237091
• CAS Number: 5707-04-0

PROPERTIES

• Purity: 98%
• Boiling Point: 120°C/20mm
• Melting Point: 60-65°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: 23/25-33-34-50/53
• Safety Statements: 20/21-28-45-60-61
• Storage Warning: Air & Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 6.1
• UN Number: UN2928
• Packing Group: II

REFERENCES

• ɑ-Phenylselenoketones can be prepared, e.g. by reaction of Li enolates with phenylselenenyl halides, and conversion to the corresponding unsaturated ketones by selenoxide elimination: J. Am. Chem. Soc., 97, 5434 (1975). Oxidizing agents include H₂O₂, mCPBA or periodate. For application to ?-diketones, see: Org. Synth. Coll., 6, 23 (1988):
  
• ?-Keto lactones undergo a similar sequence to give unsaturated lactones: J. Org. Chem., 46, 2920 (1981). -Lactones can be converted to dihydrofurans and thence to furans: J. Org. Chem., 40, 542 (1975). Similarly, cyclohexenones can be aromatized to phenols by selenenylation of the enolate and oxidation with mCPBA: Tetrahedron Lett., 23, 51 (1982). For a comprehensive review of the preparation of ɑ?-unsaturated carbonyl compounds and nitriles byselenoxide elimination, see: Org. React., 44, 1 (1993).
• Reacts with alkenylboronic acids in ionic liquids to give (Z) and (E) vinyl selenides: Tetrahedron Lett., 43, 373 (2002).
• Adds to alkenes to give trans-chloroselenylated dervatives via a selenium bridged cation: J. Org. Chem., 39, 428 (1974); Tetrahedron Lett., 4977 (1978). Also widely applied in cyclization of various molecules containing olefinic double bonds, e.g. unsaturated alcohols undergo seleno-etherification: J. Am. Chem. Soc., 102, 3784 (1980); Tetrahedron Lett., 31, 5917 (1990).
• δ-Unsaturated ketones undergo cyclofunctionalization, providing access to vic-functionalized cyclopropanes and oxygenated heterocycles: Synlett, 965 (1994):