Tris(trimethylsilyl)silane is the

organosilicon compound Organosilicon chemistry is the study of organometallic compounds containing carbon–silicon bonds, to which they are called organosilicon compounds. Most organosilicon compounds are similar to the ordinary organic compounds, being colourless, f ...

with the formula (Me₃Si)₃SiH (where Me = CH₃). It is a colorless liquid that is classified as a hydrosilane since it contains an Si-H bond. The compound is notable as having a weak Si-H bond, with a

bond dissociation energy The bond-dissociation energy (BDE, ''D''0, or ''DH°'') is one measure of the strength of a chemical bond . It can be defined as the standard enthalpy change when is cleaved by homolysis to give fragments A and B, which are usually radical ...

estimated at 84 kcal/mol. For comparison, the Si-H bond in trimethylsilane is 94 kcal/mol. With such a weak bond, the compound is used as a

reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...

to deliver hydrogen atoms. The compound has been described as an environmentally benign analogue of

tributyltin hydride Tributyltin hydride is an organotin compound with the formula (C4H9)3SnH. It is a colorless liquid that is soluble in organic solvents. The compound is used as a source of hydrogen atoms in organic synthesis. Synthesis and characterization The c ...

Reactions

The compound can be prepared by protonation of tris(trimethylsilyl)silyl lithium, which is derived from

tetrakis(trimethylsilyl)silane Tetrakis(trimethylsilyl)silane is the organosilicon compound with the formula (Me3Si)4Si (where Me = CH3). It is a colorless sublimable solid with a high melting point. The molecule has tetrahedral symmetry. The compound is notable as having sil ...

: :(Me₃Si)₄Si + MeLi → (Me₃Si)₃SiLi + Me₄Si :(Me₃Si)₃SiLi + HCl → (Me₃Si)₃SiH + LiCl Alternatively, the reaction of

trimethylsilyl chloride Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound ( silyl halide), with the formula , often abbreviated or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely u ...

and

trichlorosilane Trichlorosilane (TCS) is an inorganic compound with the formula HCl3Si. It is a colourless, volatile liquid. Purified trichlorosilane is the principal precursor to ultrapure silicon in the semiconductor industry. In water, it rapidly decomposes ...

in the presence of lithium delivers the silane directly but in modest yield: :3 Me₃SiCl + HSiCl₃ + 6 Li → (Me₃Si)₃SiH + 6 LiCl Many coordination complexes have been prepared with (Me₃Si)₃Si⁻ (hypersilyl) ligand. Chalcogenide derivatives of (Me₃Si)₃SiLi are also well developed:{{cite book , doi=10.1002/9780470166444.ch4, chapter=The Chemistry of Metal Complexes with Selenolate and Tellurolate Ligands, title=Progress in Inorganic Chemistry, year=2007, last1=Arnold, first1=John, volume=43 , pages=353–417, isbn=978-0-470-16644-4 :3 Me₃SiLi + E → (Me₃Si)₃SiELi (E = S, Se, Te)

References

Carbosilanes Trimethylsilyl compounds