Dibutyltin oxide

Dibutyltin oxide

Identifiers
CAS Number	818-08-6 Y
ChemSpider	55164 Y
ECHA InfoCard	100.011.317
PubChem CID	61221
CompTox Dashboard (EPA)	DTXSID4027315
InChI InChI=1S/2C4H9.O.Sn/c2*1-3-4-2;;/h2*1,3-4H2,2H3;; Y Key: JGFBRKRYDCGYKD-UHFFFAOYSA-N Y 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
Properties
Chemical formula	C8H18OSn
Molar mass	248.92
Appearance	white solid
Density	1.6 g/cm3
Melting point	> 300 °C (572 °F; 573 K) (decomposes 210 °C)
Hazards
Autoignition temperature	279 °C (534 °F; 552 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Dibutyltin oxide, or dibutyloxotin, is an organotin compound with the chemical formula (C₄H₉)₂SnO. It is a colorless solid that, when pure, is insoluble in organic solvents. It is used as a reagent and a catalyst.

Structure

The structure of diorganotin oxides depends on the size of the organic groups. For smaller substituents, the materials are assumed to be polymeric with five-coordinate Sn centers and 3-coordinate oxide centers. The result is a net of interconnected four-membered Sn₂O₂ and eight-membered Sn₄O₄ rings. The presence of pentacoordinate Sn centers is deduced from ¹¹⁹Sn NMR spectroscopy and ¹¹⁹Sn Mössbauer spectroscopy.

Uses

In organic synthesis, among its many applications, it is particularly useful in directing regioselective O-alkylation, acylation, and sulfonation reactions for diols and polyol. DBTO has been 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.

Dibutyltin compounds, such as dibutyltin dilaurate are widely used curing catalysts for the production of silicones and polyurethanes.

See also

Otera's catalyst