Tributyltin chloride

Tributyltin chloride

Names
Preferred IUPAC name Chlorotri(butyl)stannane
Other names Tributylchlorotin TBTC
Identifiers
CAS Number	1461-22-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:79734
ChemSpider	14368
ECHA InfoCard	100.014.508
EC Number	215-958-7
KEGG	C15224
PubChem CID	15096
UNII	CA82T4QR5F
CompTox Dashboard (EPA)	DTXSID3027403
InChI InChI=1S/3C4H9.ClH.Sn/c3*1-3-4-2;;/h3*1,3-4H2,2H3;1H;/q;;;;+1/p-1 Key: GCTFWCDSFPMHHS-UHFFFAOYSA-M
SMILES CCCC[Sn](CCCC)(CCCC)Cl
Properties
Chemical formula	C12H27ClSn
Molar mass	325.51 g·mol^−1
Appearance	colorless viscous liquid
Density	1.20 g·cm^−3 (20 °C
Melting point	−9 °C (16 °F; 264 K)
Boiling point	171 °C (340 °F; 444 K)
Refractive index (nD)	1.4903
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H312, H315, H317, H319, H360FD, H372, H410
Precautionary statements	P201, P273, P280, P301+P310+P330, P302+P352+P312, P305+P351+P338
Flash point	108 °C (226 °F; 381 K) (closed cup)
Safety data sheet (SDS)	External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tributyltin chloride is an organotin compound with the formula (C₄H₉)₃SnCl. It is a colorless liquid that is soluble in organic solvents.

Preparation and reactions

The compound is prepared by a redistribution reaction by combining stannic chloride and tetrabutyltin:

3 (C₄H₉)₄Sn + SnCl₄ → 4 (C₄H₉)₃SnCl

Tributyltin chloride hydrolyzes to the oxide [(C₄H₉)₃Sn]₂O

Tributyltin chloride is used as a precursor to other organotin compounds[1] and reagents, such as tributyltin hydride.

Literature

1. A. F. Renaldo; J. W. Labadie; J. K. Stille (1989). "Palladium-catalyzed Coupling Of Acid Chlorides With Organotin Reagents: Ethyl (E)-4-(4-nitrophenyl)-4-oxo-2-butenoate". Org. Synth. 67: 86. doi:10.15227/orgsyn.067.0086.