Tributyltin oxide

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.

Tributyltin oxide
Names
Preferred IUPAC name
Hexabutyldistannoxane
Other names
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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.244
EC Number
  • 200-268-0
KEGG
RTECS number
  • JN8750000
UNII
UN number 2788 3020 2902
  • InChI=1S/6C4H9.O.2Sn/c6*1-3-4-2;;;/h6*1,3-4H2,2H3;;; checkY
    Key: APQHKWPGGHMYKJ-UHFFFAOYSA-N checkY
  • 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
    Key: APQHKWPGGHMYKJ-XAMPVVILAF
  • CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC
Properties
C24H54OSn2
Molar mass 596.112
Appearance colorless oil
Density 1.17 g/mL at 25 °C (lit.)
Melting point −45 °C (−49 °F; 228 K)
Boiling point 180 °C (356 °F; 453 K) at 2 mm Hg
20 mg/L
Solubility Hydrocarbons, alcohols, ethers, THF
log P 5.02[1]
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H312, H315, H319, H331, H372, H373, H410
P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P362, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

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.[2] It is now considered a severe marine pollutant and a Substance of Very High Concern by the EU.[3] Today, it is mainly used in wood preservation[4]

References
  1. "Tributyltin oxide_msds".
  2. "Focus on IMO - Anti-fouling systems" (PDF). International Maritime Organisation.
  3. Organotin Chemistry, Second Edition. Alwyn G. Davies, 2004, Wiley-VCH Verlag GmbH & Co. KGaA. ISBN 3-527-31023-1
  4. Davies, Alwyn George. (2004) Organotin Chemistry, 2nd Edition Weinheim: Wiley-VCH. ISBN 978-3-527-31023-4
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