Tributyltin Hydride

Chemical properties

clear colourless liquid

The Uses of Tributyltin Hydride

Tributyltin hydride the most commonly used tin hydride，it is less toxic than the more volatile trierhyl and trimethyl analogues, and it is therefore the most widely used organostannane.
Tributyltin hydride, the reagent of choice for generating alkyl radical, is also widely used in aryl radical cyclization. Other reagents developed for this purpose include samarium diiodide, palladium reagents organosilanes as well as manganese triacetate and transition metals for carbocyclization.

The Uses of Tributyltin Hydride

A widely used radical reagent used in reductive cleavage,1 radical dehalogenation, and intramolecular radical cyclization.2

The Uses of Tributyltin Hydride

Tributyltin hydride is used to effect carbon—carbon bond formation with the displacement of halide from a suitably oriented haloalkyl group.

What are the applications of Application

Tributyltin hydride is a reducing agent acting by radical intermediates

What are the applications of Application

Has been reviewed. Catalyzes the Si-H reduction of α,β-unsaturated ketones. Useful in the reductive amination of ketones and aldehydes to form 3° amines.

Hazard

Moderately toxic by inhalation.

Safety Profile

Moderately toxic by inhalation. When heated to decomposition it emits acrid smoke and irritating fumes. See also TIN COMPOUNDS.

Purification Methods

Dissolve it in Et2O, add quinol (500mg for 300mL, to stabilize it), dry over Na2SO4, filter, evaporate and distil it under dry N2. It is a clear liquid if dry and decomposes very slowly. In the presence of H2O, traces of tributyl tin hydroxide are formed in a few days. Store it in sealed glass ampoules in small aliquots. It is estimated by reaction with aqueous NaOH when H2 is liberated. CARE: stored samples may be under pressure due to liberated H2. [Van Der Kerk et al. J Appl Chem 7 366 1937, Ono et al. Tetrahedron 41 4013 1985, Neuman Synthesis 665 1987, Curran Synthesis 417 1988, Beilstein 4 IV 4312.]