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

Tributyltin chloride
Names
Preferred IUPAC name
Chlorotri(butyl)stannane
Other names
Tributylchlorotin
TBTC
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.508 Edit this at Wikidata
EC Number
  • 215-958-7
KEGG
UNII
  • InChI=1S/3C4H9.ClH.Sn/c3*1-3-4-2;;/h3*1,3-4H2,2H3;1H;/q;;;;+1/p-1
    Key: GCTFWCDSFPMHHS-UHFFFAOYSA-M
  • CCCC[Sn](CCCC)(CCCC)Cl
Properties
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)
1.4903
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H312, H315, H317, H319, H360FD, H372, H410
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).

Preparation and reactions

edit

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

edit
  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.