Sodium triethylborohydride is an

organoboron compound Organoborane or organoboron compounds are chemical compounds of boron and carbon that are Organic compound, organic derivatives of BH3, for example trialkyl boranes. Organoboron chemistry or organoborane chemistry is the chemistry of these compoun ...

with the formula NaBH(C₂H₅)₃. It is a colorless,

pyrophoric A substance is pyrophoric (from grc-gre, πυροφόρος, , 'fire-bearing') if it ignites spontaneously in air at or below (for gases) or within 5 minutes after coming into contact with air (for liquids and solids). Examples are organolith ...

solid that is commercially available in

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) at ...

solution, unlike the related LiBH(C₂H₅)₃ which is typically sold as a THF solution. It is commonly used for the reductive activation of

homogeneous catalyst In chemistry, homogeneous catalysis is catalysis by a soluble catalyst in a solution. Homogeneous catalysis refers to reactions where the catalyst is in the same phase as the reactants, principally in solution. In contrast, heterogeneous catalysis ...

s, converting metal halides to hydrides. Sodium triethylborohydride has been prepared by treating a hot toluene slurry of sodium hydride with triethylborane. The trimethylborohydride analogue, which is assumed to be structurally similar to the triethylborohydride, adopts a tetrameric structure in toluene solution.Bell, N. A.; Coates, G. E.; Heslop, J. A., "Sodium hydridotrimethylboronate and its ether solvate. Study of hydridotrialkylboronates as reagents for the preparation of beryllium hydrides", J. Organomet. Chem. 1987, volume 329, 287-291. {{doi, 10.1016/0022-328X(87)80062-1.

References

Sodium compounds Borohydrides Organoboranes Reducing agents