tributyltin oxide
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470613357
| Name =
| ImageFile = Tributyltin oxide structure.svg
| ImageSize =
| ImageFile1 = Tributyltin-oxide-3D-vdW.png
| ImageSize1 =
| PIN = Hexabutyldistannoxane
| OtherNames = Bis(tributyltin) oxide, tri-n-butyltin oxide, bis(tri-n-butyltin)oxide, AW 75-D, Bio-Met TBTO, Biomet, Biomet 75, BTO, Butinox, C-SN-9
| SystematicName =
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 56-35-9
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10218152
| ChEBI = 81543
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 511667
| EC_number = 200-268-0
| RTECS = JN8750000
| UNNumber = 2788 3020 2902
| PubChem = 16682746
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C18149
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3353Q84MKM
| InChI = 1/6C4H9.O.2Sn/c6*1-3-4-2;;;/h6*1,3-4H2,2H3;;;/rC24H54OSn2/c1-7-13-19-26(20-14-8-2,21-15-9-3)25-27(22-16-10-4,23-17-11-5)24-18-12-6/h7-24H2,1-6H3
| InChIKey = APQHKWPGGHMYKJ-XAMPVVILAF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/6C4H9.O.2Sn/c6*1-3-4-2;;;/h6*1,3-4H2,2H3;;;
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = APQHKWPGGHMYKJ-UHFFFAOYSA-N
| SMILES = CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC
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| Section2 = {{Chembox Properties
| Formula = C24H54OSn2
| MolarMass = 596.112
| Appearance = colorless oil
| Density = 1.17 g/mL at 25 °C (lit.)
| MeltingPtC = -45
| BoilingPtC = 180
| BoilingPt_notes = at 2 mm Hg
| Solubility = 20 mg/L
| SolubleOther = Hydrocarbons, alcohols, ethers, THF
| LogP = 5.02{{Cite web|url=https://www.chemsrc.com/en/cas/56-35-9_743423.html|title=Tributyltin oxide_msds}}
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| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|312|315|319|331|372|373|410}}
| PPhrases = {{P-phrases|260|261|264|270|271|273|280|301+310|302+352|304+340|305+351+338|311|312|314|321|322|330|332+313|337+313|362|363|391|403+233|405|501}}
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Tributyltin oxide (TBTO) is an organotin compound chiefly used as a biocide (fungicide and molluscicide), especially a wood preservative. Its chemical formula is [(C4H9)3Sn]2O. It is a colorless viscous liquid. It is poorly soluble in water (20 ppm) but highly soluble in organic solvents. It is a potent skin irritant.
Historically, tributyltin oxide's biggest application was as a marine anti-biofouling agent. Concerns over toxicity of these compounds have led to a worldwide ban by the International Maritime Organization.{{cite news | url=http://www.imo.org/OurWork/Environment/Anti-foulingSystems/Documents/FOULING2003.pdf | title=Focus on IMO - Anti-fouling systems | publisher=International Maritime Organisation}} It is now considered a severe marine pollutant and a Substance of Very High Concern by the EU.Organotin Chemistry, Second Edition. Alwyn G. Davies, 2004, Wiley-VCH Verlag GmbH & Co. KGaA. {{ISBN|3-527-31023-1}} Today, it is mainly used in wood preservation.Davies, Alwyn George. (2004) Organotin Chemistry, 2nd Edition Weinheim: Wiley-VCH. {{ISBN|978-3-527-31023-4}}
References
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External links
- [https://web.archive.org/web/20060411081425/http://www.npi.gov.au/database/substance-info/profiles/66.html National Pollutant Inventory Fact Sheet for organotins]
- {{PPDB|2585}}