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{{chembox |
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| verifiedrevid = 401986969 |
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| verifiedrevid = 444032680 |
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| ImageFile = Dibutyltinoxide.png |
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| ImageSize = 150px |
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| IUPACName = |
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| ImageFile = Bu2SnObetter.svg |
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| IUPACName = dibutylstannanone |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 55164 |
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| ChemSpiderID = 55164 |
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| EC_number = 212-449-1 |
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| RTECS = WH7175000 |
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| UNNumber = 3146 |
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| 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 |
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| 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 |
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| InChIKey = JGFBRKRYDCGYKD-KVGUGNSWAI |
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| InChIKey = JGFBRKRYDCGYKD-KVGUGNSWAI |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 818-08-6 |
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| CASNo = 818-08-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 61221 |
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| UNII = T435H74FO0 |
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| SMILES = O=(CCCC)CCCC |
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| PubChem = 61221 |
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| SMILES = CCCC(=O)CCCC |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>8</sub>H<sub>18</sub>OSn |
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| Formula = C<sub>8</sub>H<sub>18</sub>OSn |
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| MolarMass = 248.92 |
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| MolarMass = 248.92 |
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| Appearance = white solid |
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| Appearance = white solid |
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| Density = 1.6 g/cm<sup>3</sup> |
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| Density = 1.6 g/cm<sup>3</sup> |
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| MeltingPt = >300 °C (decomp. 210 °C) |
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| MeltingPt= > |
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| MeltingPtC = 300 |
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| MeltingPt_notes = (decomposes 210 °C) |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = 279 °C |
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| AutoignitionPtC = 279 |
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| RPhrases = R: 21-25-36/38-48/23/25-50/53 |
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| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}} |
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| SPhrases = S: 1/2-35-36/37/39-45-60-61 |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|302|315|317|318|341|360|370|372|373|410|411}} |
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| PPhrases = {{P-phrases|201|202|260|261|264|270|272|273|280|281|301+310|301+312|302+352|305+351+338|307+311|308+313|310|314|321|330|332+313|333+313|362|363|391|405|501}} |
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'''Dibutyltin oxide''', or '''dibutyloxotin''', is an ] compound used in organic synthesis. Among many synthetic applications, it is particularly useful in regioselective ], ], and ] reactions for starting materials containing ] ]. |
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'''Dibutyltin oxide''', or '''dibutyloxotin''', is an ] compound with the ] (C<sub>4</sub>H<sub>9</sub>)<sub>2</sub>SnO. It is a colorless solid that, when pure, is insoluble in organic solvents. It is used as a reagent and a ].<ref name=Davies>Davies, Alwyn G. "Organotin Chemistry", 2nd Edition, 2004, Wiley-VCH: Weinheim. {{ISBN|978-3-527-31023-4}}.</ref> |
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== Applications == |
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==Structure== |
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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 Sn<sub>2</sub>O<sub>2</sub> and eight-membered Sn<sub>4</sub>O<sub>4</sub> rings. The presence of pentacoordinate Sn centers is deduced from <sup>119</sup>Sn ]<ref>{{cite journal |last1=Harris |first1=Robin K. |last2=Sebald |first2=Angelika |title=The structure of polymeric dialkyltin oxides (R Me, nBu) as probed by high-resolution solid-state 119Sn NMR |journal=Journal of Organometallic Chemistry |date=September 1987 |volume=331 |issue=2 |pages=C9–C12 |doi=10.1016/0022-328X(87)80030-X}}</ref> and <sup>119</sup>Sn ].<ref>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}}</ref> |
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==Uses== |
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Dibutyltin oxide (DBTO) may be used in the regioselective ] (a specific type of sulfonation) of certain ] to selectively tosylate ] and ] alcohols over more sterically-hindered alcohols: |
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In organic synthesis, among its many applications, it is particularly useful in directing regioselective O-], ], and ] reactions for ]s and polyol. DBTO has been used in the regioselective ] (a specific type of sulfonation) of certain ] to selectively tosylate ] and ] alcohols over more sterically-hindered alcohols.<ref>T. V. (Babu) RajanBabu, Junzo Otera "Di-n-butyltin Oxide" eEROS, 2005. {{doi|10.1002/047084289X.rd071.pub2}}</ref> It also finds use as a ] catalyst.{{Citation needed|date=December 2024}} |
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Dibutyltin compounds, such as ] are widely used curing catalysts for the production of ]s and ]s.<ref>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}}</ref> |
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==See also== |
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