Bis(tri-n-butyltin) oxide

• Catalog No.: A13242
• CAS Number: 56-35-9
• M. F.: C24H54OSn2
• M. W.: 596.08696
• Purity: 97%

SYNONYMS

• Title: 双(三正丁基锡)氧化物
• IUPAC name: bis(tributylstannylium) oxidandiide
• IUPAC Traditional name: bis(tributylstannylium) oxidandiide
• Synonyms: Tri-n-butyltin oxide; Hexabutyl distannoxane

DATABASE IDS

• CAS Number: 56-35-9
• Beilstein Number: 745057
• EC Number: 200-268-0
• MDL Number: MFCD00009418

PROPERTIES

• Purity: 97%
• Boiling Point: 179-180°C/2mm
• Density: 1.172
• Flash Point: 168°C(334°F)
• Melting Point: -45°C
• Refractive Index: 1.4865
• GHS Hazard statements: H301-H311-H315-H319-H360-H372-H400-H410
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P280-P273-P309-P310-P501A
• Risk Statements: 60-21-25-36/38-48/23/25-50/53-63
• RTECS: JN8750000
• Safety Statements: 36/37/39-45-60-61
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2788
• Packing Group: III

REFERENCES

• Reacts with alcohols to give tri-n-butylstannyl ethers which, for simple alcohols, are very susceptible to hydrolysis: Synthesis, 56 (1969); J. Organomet. Chem., 110, C57 (1976). In combination with bromine or NBS, allylic, benzylic and secondary alcohols are oxidized to carbonyl compounds, enabling the selective oxidation of secondary, in the presence of primary, alcohols: Bull. Chem. Soc. Jpn., 49, 1656 (1976); Tetrahedron Lett., 4597 (1976); J. Am. Chem. Soc., 98, 1629 (1976). Similarly, sulfides give sulfoxides with no over-oxidation to sulfones: Tetrahedron Lett., 2413 (1977).
• Reacts with terminal alkynes to give alkynyl tin reagents. Where these reagents have electron-withdrawing substituents, they undergo regioselective cycloaddition with 1,3-dienes: Tetrahedron, 45, 1145 (1989):
  
• Converts thioamides to nitriles, as does Di-n-butyltin oxide, L14491: J .Org. Chem., 47, 4594 (1982).
• Reagent for mild, selective non-hydrolytic deprotection of esters: Tetrahedron Lett., 32, 4239 (1991); J. Org. Chem., 59, 7259 (1994); Tetrahedron Lett., 36, 3311 (1995).