Tributyltin oxide

Tributyltin oxide
Names
	IUPAC name hexabutyldistannoxane
	Other names bis(tributyltin) oxide, bis(tri-n-butyltin)oxide, AW 75-D, Bio-Met TBTO, Biomet, Biomet 75, BTO, Butinox, C-SN-9
Identifiers
CAS Number	56-35-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL511667 ;
ChemSpider	10218152 ;
ECHA InfoCard	100.000.244
KEGG	C18149 ;
PubChem CID	16682746;
UNII	3353Q84MKM ;
CompTox Dashboard (EPA)	DTXSID9020166 ;
	InChI InChI=1S/6C4H9.O.2Sn/c61-3-4-2;;;/h61,3-4H2,2H3;;; Key: APQHKWPGGHMYKJ-UHFFFAOYSA-N ; InChI=1/6C4H9.O.2Sn/c61-3-4-2;;;/h61,3-4H2,2H3;;;/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;
	SMILES CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC;
Properties
Chemical formula	C24H54OSn2
Molar mass	596.112
Appearance	colorless oil
Melting point	−45 °C (−49 °F; 228 K)
Boiling point	180 °C (356 °F; 453 K) at 2 mm Hg
Solubility in water	0.002 g/100 mL
log P	5.02
Hazards
R-phrases (outdated)	R21 R25 R36/38 R48/23/25 R50/53
S-phrases (outdated)	S36/37/39 S45 S60 S61
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 compounds had been used as marine anti-biofouling agents. 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]

References

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

External links

National Pollutant Inventory Fact Sheet for organotins
Tributyltin oxide in the Pesticide Properties DataBase (PPDB)

[chemsrc-1] "Tributyltin oxide_msds".

[IMO-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

[1]

[2]

[3]

Names


IUPAC name hexabutyldistannoxane
Other names bis(tributyltin) oxide, bis(tri-n-butyltin)oxide, AW 75-D, Bio-Met TBTO, Biomet, Biomet 75, BTO, Butinox, C-SN-9
Identifiers
CAS Number	56-35-9
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL511667
ChemSpider	10218152
ECHA InfoCard	100.000.244
KEGG	C18149
PubChem CID	16682746
UNII	3353Q84MKM
CompTox Dashboard (EPA)	DTXSID9020166
InChI InChI=1S/6C4H9.O.2Sn/c61-3-4-2;;;/h61,3-4H2,2H3;;; Key: APQHKWPGGHMYKJ-UHFFFAOYSA-N InChI=1/6C4H9.O.2Sn/c61-3-4-2;;;/h61,3-4H2,2H3;;;/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
SMILES CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC
Properties
Chemical formula	C₂₄H₅₄OSn₂
Molar mass	596.112
Appearance	colorless oil
Melting point	−45 °C (−49 °F; 228 K)
Boiling point	180 °C (356 °F; 453 K) at 2 mm Hg
Solubility in water	0.002 g/100 mL
log P	5.02^[1]
Hazards
R-phrases (outdated)	R21 R25 R36/38 R48/23/25 R50/53
S-phrases (outdated)	S36/37/39 S45 S60 S61
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).