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Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, [5] is an inorganic compound with the formula Na B H 4 (sometimes written as Na[BH 4]). It is a white crystalline solid, usually encountered as an aqueous basic solution. Sodium borohydride is a reducing agent that finds application in papermaking and dye ...
The relatively weak reducer sodium borohydride is typically used for reducing ketones and aldehydes. It tolerates many functional groups (nitro group, nitrile, ester). [6] In their handling properties, lithium aluminium hydride and sodium borohydride (and their derivatives) strongly differ.
α,β-Unsaturated nitro compounds can be reduced to saturated amines by: Catalytic hydrogenation over palladium-on-carbon; Iron metal; Lithium aluminium hydride [27] (Note: Hydroxylamines and oximes are typical impurities.) Lithium borohydride or sodium borohydride and trimethylsilyl chloride [28] Red-Al [29]
Sodium borohydride and lithium aluminium hydride are commonly used for the reduction of organic compounds. [3] [4] These two reagents are on the extremes of reactivity—whereas lithium aluminium hydride reacts with nearly all reducible functional groups, sodium borohydride reacts with a much more limited range of functional groups.
Sodium triacetoxyborohydride (STAB, NaBH(OAc) 3) is a common reducing agent for reductive aminations. STAB selectively reduces the imine intermediate formed through dehydration of the molecule. [8] STAB is a weaker reductant than NaBH 4, and can preferentially reduce the imine group in the presence of other reduction-sensitive functional groups ...
Since sodium cyanoborohydride is a mild reducing agent, it gives good chemoselectivity for reaction with certain functional groups in the presence of others. For example, sodium cyanoborohydride is generally incapable of reducing amides, ethers, esters and lactones, nitriles, or epoxides. [8]
Different hydride reagents have different reactivity towards functional groups so they can be selected according to the desired outcome. [8] Examples include the greater relative chemoselectivity of sodium borohydride versus lithium aluminium hydride for the organic reduction of 4-nitro-2-chlorobenzonitrile to the corresponding aniline, 4-amino ...
Ball-and-stick model of the tetrahydroborate anion, [BH 4] −. Borohydride refers to the anion [B H 4] −, which is also called tetrahydridoborate, and its salts. [1] Borohydride or hydroborate is also the term used for compounds containing [BH 4−n X n] −, where n is an integer from 0 to 3, for example cyanoborohydride or cyanotrihydroborate [BH 3 (CN)] − and triethylborohydride or ...