Osmium(VIII) oxide

• Catalog No.: 12103
• CAS Number: 20816-12-0
• M. F.: O4Os
• M. W.: 254.2276
• Purity: 99.8% (metals basis), Os 74.4% min

SYNONYMS

• Title: 氧化锇(VIII)
• IUPAC name: osmium(8+) ion tetraoxidandiide
• IUPAC Traditional name: osmium(8+) ion tetraoxidandiide
• Synonyms: Osmic acid; Osmium tetroxide

DATABASE IDS

• Merck Index: 146893
• MDL Number: MFCD00011150
• CAS Number: 20816-12-0
• EC Number: 244-058-7

PROPERTIES

• Purity: 99.8% (metals basis), Os 74.4% min
• Apperance: Crystalline
• Boiling Point: 130°C
• Melting Point: 40.6°C
• Solubility: Soluble in chloroform, alcohol and ethers
• GHS Hazard statements: H300-H310-H330-H314
• European Hazard Symbols: Highly toxic (T+)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A
• Risk Statements: 26/27/28-34
• Safety Statements: 7/9-26-45
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2471
• Packing Group: I

REFERENCES

• See also Potassium osmium(VI) oxide dihydrate, L18120.
• Reagent for the cis-dihydroxylation of double bonds via cyclic osmate esters. Reviews: Synthesis, 229 (1974); Chem. Rev., 80, 187 (1980). Because of the cost and toxicity of the osmium compounds, various co-oxidants have been used to regenerate the reagent, including:
• H₂O₂: J. Am. Chem. Soc., 58, 1302 (1936); 59, 2345 (1937); NaIO₄: J. Org. Chem., 21, 478 (1956); tert-BuOOH in the presence of Bu₄NOH or Bu₄NOAc: J. Am. Chem. Soc., 98, 1986 (1976); J. Org. Chem., 43, 2063 (1978); Trimethylamine N-oxide in pyridine, permitting the dihydroxylation of hindered double bonds: Tetrahedron Lett., 21, 449 (1980); N-Methylmorpholine-N-oxide (NMMO): Tetrahedron Lett., 1973 (1976); for examples using this system, with <1% catalyst, see: Org. Synth. Coll., 6, 342 (1988). Possible overoxidation of the diol can be avoided by trapping with Benzeneboronic acid, A14257: Chem. Lett., 1721 (1988). Recyclable systems for Os, utilizing the ionic liquids 1-Ethyl-3-methylimidazolium tetrafluoroborate, L19763: Tetrahedron Lett., 43, 6849 (2002), or 1-n-Butyl-3-methylimidazolium hexafluorophosphate, L19086, and DMAP: Org. Lett., 4, 2197 (2002), have been reported to give excellent results. In conjunction with NaIO₄, oxidative cleavage of alkenes can be effected. For an improved procedure, see: Org. Lett., 6, 3217 (2004).
• Sharpless and others have developed techniques for catalytic asymmetric dihydroxylation (ADH), in the presence of chiral amines such as dihydroquinidine, with NMMO as stoichiometric oxidant: J. Am. Chem. Soc., 102, 4263 (1980); 110, 1968 (1988); for practical details (stilbene to (R,R)-stilbenediol), see: Org. Synth. Coll., 9, 383 (1998). For a review of catalytic ADH, see: Chem. Rev., 94, 2483 (1994).
• Can also be used, in combination with Chloramine-T trihydrate, A12044, for vicinal oxyamination of olefins: Org. Synth. Coll., 7, 375 (1990).
• Using KClO₄ to regenerate the reagent, alkynes have been oxidized to ɑ-diketones: J. Org. Chem., 43, 4245 (1978). Terminal alkynes can be converted to ɑ-keto esters by hydroxylation of their 1-silyl derivatives: Tetrahedron, 46, 2573 (1990).