Dibutyltin oxide

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.[1]

Dibutyltin oxide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.317
EC Number
  • 212-449-1
RTECS number
  • WH7175000
UNII
UN number 3146
  • 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
  • CCCC[Sn](=O)CCCC
Properties
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
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H302, H315, H317, H318, H341, H360, H370, H372, H373, H410, H411
P201, P202, P260, P261, P264, P270, P272, P273, P280, P281, P301+P310, P301+P312, P302+P352, P305+P351+P338, P307+P311, P308+P313, P310, P314, P321, P330, P332+P313, P333+P313, P362, P363, P391, P405, P501
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).
checkY verify (what is checkY☒N ?)
Infobox references

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[2] and 119Sn Mössbauer spectroscopy.[3]

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.[4] It also finds use as a transesterification catalyst.

Dibutyltin compounds, such as dibutyltin dilaurate are widely used curing catalysts for the production of silicones and polyurethanes.[5]

See also

Otera's catalyst

References
  1. Davies, Alwyn G. "Organotin Chemistry", 2nd Edition, 2004, Wiley-VCH: Weinheim. ISBN 978-3-527-31023-4.
  2. Harris, Robin K.; Sebald, Angelika (September 1987). "The structure of polymeric dialkyltin oxides [R2SnO] (R  Me, nBu) as probed by high-resolution solid-state 119Sn NMR". Journal of Organometallic Chemistry. 331 (2): C9–C12. doi:10.1016/0022-328X(87)80030-X.
  3. Beckmann, Jens; Jurkschat, Klaus; Rabe, Stephanie; Schuermann, Markus "Hexakis(2,4,6-triisopropylphenyl)cyclotristannoxane - a molecular diorganotin oxide with kinetically inert Sn-O bonds" Zeitschrift für Anorganische und Allgemeine Chemie 2001, volume 627, 2413-2419. doi:10.1002/1521-3749(200110)627:10<2413::AID-ZAAC2413>3.0.CO;2-H
  4. T. V. (Babu) RajanBabu, Junzo Otera "Di-n-butyltin Oxide" eEROS, 2005. doi:10.1002/047084289X.rd071.pub2
  5. Jorge Cervantes1, Ramón Zárraga, Carmen Salazar-Hernández "Organotin catalysts in Organosilicon Chemistry" Appl. Organometal. Chem. 2012, volume 26, 157–163. doi:10.1002/aoc.2832
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