bis(tributylstannylium) oxidandiide

• ChemBase ID: 295279
• Molecular Formular: C24H54OSn2
• Molecular Mass: 596.08696
• Monoisotopic Mass: 598.22185435
• SMILES: CCCC[Sn+](CCCC)CCCC.CCCC[Sn+](CCCC)CCCC.[O-2]
• Canonical SMILES: CCCC[Sn+](CCCC)CCCC.CCCC[Sn+](CCCC)CCCC.[O-2]
• InChI: InChI=1S/6C4H9.O.2Sn/c6*1-3-4-2;;;/h6*1,3-4H2,2H3;;;/q;;;;;;-2;2*+1
• InChIKey: VFWHRLHTRNDINW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 56-35-9
• EC Number: 200-268-0
• MDL Number: MFCD00009418
• Beilstein Number: 745057
• PubChem SID: 180680810
• PubChem CID: 9851553

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.5287
• LogD (pH = 7.4): 3.5287
• Log P: 3.5287
• Molar Refractivity: 58.4157 cm^3
• Polarizability: 27.806976 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: -45°C
• Boiling Point: 179-180°C/2mm
• Flash Point: 168°C(334°F)
• Density: 1.172
• Refractive Index: 1.4865

Safety Information

• RTECS: JN8750000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: UN2788
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 60-21-25-36/38-48/23/25-50/53-63
• Safety Statements: 36/37/39-45-60-61
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Hazard statements: H301-H311-H315-H319-H360-H372-H400-H410
• GHS Precautionary statements: P280-P273-P309-P310-P501A

Product Information

• Purity: 97%

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).