Borohydrides
Encyclopedia
A borohydride is a compound containing the tetrahydridoborate(III) ion, B
Boron
Boron is the chemical element with atomic number 5 and the chemical symbol B. Boron is a metalloid. Because boron is not produced by stellar nucleosynthesis, it is a low-abundance element in both the solar system and the Earth's crust. However, boron is concentrated on Earth by the...

H4
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

. Borohydride is a term also used for compounds containing BH3CN- (cyanotrihydroborate) and BH(C2H5)3- (triethylborohydride). Such compounds are mainly used as reducing agent
Reducing agent
A reducing agent is the element or compound in a reduction-oxidation reaction that donates an electron to another species; however, since the reducer loses an electron we say it is "oxidized"...

s in organic synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...

. The most important borohydride is sodium borohydride
Sodium borohydride
Sodium borohydride, also known as sodium tetrahydridoborate, is an inorganic compound with the formula NaBH4. This white solid, usually encountered as a powder, is a versatile reducing agent that finds wide application in chemistry, both in the laboratory and on a technical scale. Large amounts are...

, but other salts are well known (see Table).

Coordination complexes

Borohydrides are excellent ligands for metal ions. In most such compounds, the BH4- ligand is bidentate. The binary borohydrides containing only BH4- ligands are often fairly volatile. One example is uranium borohydride
Uranium borohydride
Uranium borohydride U4 is a volatile uranium complex with borohydride. This green-coloured compound is polymeric in the solid but evaporates to a tetrahedral monomer.-Preparation:...

.
Selected Properties of Various Borohydride Salts
Hydride CAS registry number Mol.Wt. Hydrogen Density Density g/cm3 m.p. (°C) solubility in water (g/100 mL, 25 °C) solubility in CH3OH (g/100 mL, 25 °C)solubility in ether (g/100 mL, 25 °C)solubility in THF (g/100 mL, 25 °C)
LiBH4
Lithium borohydride
Lithium borohydride is a tetrahydroborate and known in organic synthesis as a reducing agent for esters. Although less common than the related sodium borohydride, the lithium salt offers some advantages of being highly soluble in ethers and being a stronger reducing agent but still safer to...


[16949-15-8]
21.78 18.5 0.66 280 20.9 decomp. (44 in EtOH) 4.3 22.5
NaBH4
Sodium borohydride
Sodium borohydride, also known as sodium tetrahydridoborate, is an inorganic compound with the formula NaBH4. This white solid, usually encountered as a powder, is a versatile reducing agent that finds wide application in chemistry, both in the laboratory and on a technical scale. Large amounts are...


[16940-66-2]
37.83 10.6 1.07 505 55 16.4 (20 °C) insol. 0.1 (20 °C)
NaBH3CN
Sodium cyanoborohydride
Sodium cyanoborohydride is the inorganic compound with the formula NaBH3. This colourless salt is widely used in organic synthesis for the reduction of imines.-Preparation and use:...


[25895-60-7]
62.84 6.4 1.20 240 with deccomp. deccomp. 217 insol. 36
KBH4
[13762-51-1]
53.94 7.4 1.17 585 (under H2) 19 insol. insol. insol.
LiBH(C2H5)3
Lithium triethylborohydride
Lithium triethylborohydride , commonly abbreviated to LiTEBH or Superhydride, is a powerful and selective reducing agent used in inorganic and organic chemistry. LiTEBH is far more powerful than lithium borohydride and more powerful than lithium aluminium hydride in many cases...


[22560-16-3]
105.94 0.95 unknown unknown decomp. decomp. na high (supplied commercially)
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