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Tributyltin chloride

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Tributyltin chloride
Names
Preferred IUPAC name Chlorotri(butyl)stannane
Other names Tributylchlorotin
TBTC
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.508 Edit this at Wikidata
EC Number
  • 215-958-7
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/3C4H9.ClH.Sn/c3*1-3-4-2;;/h3*1,3-4H2,2H3;1H;/q;;;;+1/p-1Key: GCTFWCDSFPMHHS-UHFFFAOYSA-M
SMILES
  • CCCC(CCCC)(CCCC)Cl
Properties
Chemical formula C12H27ClSn
Molar mass 325.51 g·mol
Appearance colorless viscous liquid
Density 1.20 g·cm (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 GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
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 , 100 kPa). Infobox references
Chemical compound

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 2O

Tributyltin chloride is used as a precursor to other organotin compounds 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.
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