5544. Lithium Triethylborohydride

Nomenclature

CAS number: 22560-16-3
(T-4)-Lithium triethylhydroborate(1); Super-Hydride (Aldrich).
C6H16BLi; mol wt 105.94.
C 68.02%, H 15.22%, B 10.20%, Li 6.55%.
LiBH(C2H5)3.

Description and references

Commercial product is available in THF solution. Prepn: H. C. Brown et al., J. Am. Chem. Soc. 75, 192 (1953); P. Binger et al., Ann. 717, 21 (1968); H. C. Brown et al., Inorg. Chem. 16, 2229 (1977). Mechanism of reduction of organic halides: E. C. Ashby et al., J. Org. Chem. 49, 4505 (1984). Use as a reducing agent in organic and inorganic synthesis: H. C. Brown et al., J. Org. Chem. 45, 1 (1980); S. Krishnamurthy, H. C. Brown, ibid. 48, 3085 (1983); H. C. Brown, S.-C. Kim, ibid. 49, 1064 (1984); B. E. Blough, F. I. Carroll, Tetrahedron Lett. 34, 7239 (1993); C. K. Yee et al., Langmuir 15, 3486 (1999); H. Tanaka, K. Ogasawara, Tetrahedron Lett. 43, 4417 (2002).

Properties

Colorless crystals, mp 66-67° (Binger). Also reported as white needles from benzene, mp 78-83° (dec) (Brown, 1977). Moderately sol in benzene, toluene, n-hexane. Unstable in air. Reacts violently with water.

Use

Powerful and selective reducing agent.