Di-n-butyltin oxide

• Catalog No.: L14491
• CAS Number: 818-08-6
• M. F.: C8H18OSn
• M. W.: 248.92892
• Purity: 98%

SYNONYMS

• Title: 二正丁基氧化锡
• IUPAC name: dibutylstannanone
• IUPAC Traditional name: dibutyltin oxide
• Synonyms: Dibutyloxotin

DATABASE IDS

• EC Number: 212-449-1
• Beilstein Number: 4126243
• MDL Number: MFCD00001992
• CAS Number: 818-08-6

PROPERTIES

• Purity: 98%
• Melting Point: >300°C
• GHS Hazard statements: H301-H319-H411-H401
• European Hazard Symbols: Toxic (T)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P280-P301+P310-P305+P351+P338-P321-P405-P501A
• Risk Statements: 25-36-51/53
• RTECS: WH7175000
• Safety Statements: 26-36/37-45-61
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN3146
• Packing Group: II

REFERENCES

• Reacts with 1,2-diols to form 5-membered cyclic dibutylstannoxane derivatives. For use in the glycoside field, see: Synthesis, 409 (1995). Formation of these derivatives is greatly accelerated by microwave irradiation: Synlett, 89 (1994). The stannylene derivatives are activated to electrophilic attack:
• With bromine, the ɑ-hydroxy ketone is formed: J. Chem. Soc., Perkin 1, 1568 (1979). With acyl or sulfonyl chlorides, overall regioselective monoacylation of the diol at the more substituted hydroxyl can be achieved: Tetrahedron Lett., 21, 221 (1980); J. Chem. Soc., Chem. Commun., 1457 (1985); J. Org. Chem., 55, 5132 (1990); 61, 5257 (1996). Selective monotosylation of 1,2-diols has also been achieved catalytically: Tetrahedron Lett., 41, 3773 (2000).
• Catalyst for lactonization and lactamization reactions: J. Am. Chem. Soc., 102, 7578 (1980), particularly useful in the formation of macrolides: J. Am. Chem. Soc., 105, 7130 (1983). For catalysis of N-acylation of hydroxy alcohols with microwave irradiation, see: J. Org. Chem., 61, 5264 (1996).
• Promotes the cycloaddition of Trimethylsilyl azide, L00173 to nitriles to give 5-aryltetrazoles, some of which are important as angiotensin II inhibitors: J. Org. Chem., 58, 4139 (1993):
  
• Catalyst for the dehydration of amides to nitriles under neutral conditions: Synthesis, 1724 (1999); for use of microwave irradiation, see: J. Org. Chem., 64, 1713 (1999).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 1847 (2004).