Dibutyltin oxide

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Dibutyltin oxide
Names
IUPAC name
dibutylstannanone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.317 Edit this at Wikidata
  • InChI=1S/2C4H9.O.Sn/c2*1-3-4-2;;/h2*1,3-4H2,2H3;; checkY
    Key: JGFBRKRYDCGYKD-UHFFFAOYSA-N checkY
  • InChI=1/2C4H9.O.Sn/c2*1-3-4-2;;/h2*1,3-4H2,2H3;;/rC8H18OSn/c1-3-5-7-10(9)8-6-4-2/h3-8H2,1-2H3
    Key: JGFBRKRYDCGYKD-KVGUGNSWAI
  • O=[Sn](CCCC)CCCC
Properties
C8H18OSn
Molar mass 248.92
Appearance white solid
Density 1.6 g/cm3
Melting point >300 °C (decomp. 210 °C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Dibutyltin oxide, or dibutyloxotin, is an organotin compound used in organic synthesis. Among many synthetic applications, it is particularly useful in regioselective alkylation, acylation, and sulfonation reactions for starting materials containing alcohol functional groups.

Applications

Dibutyltin oxide (DBTO) may be used in the regioselective tosylation (a specific type of sulfonation) of certain polyols to selectively tosylate primary alcohols and exocyclic alcohols over more sterically-hindered alcohols:

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