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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 ...
Sodium borohydride can, under some circumstances, be used for ester reduction, especially with additives. [ 1 ] Forming aldehydes from carboxylic acid derivatives is challenging because weaker reducing agents (NaBH 4 ) are often very slow at reducing esters and carboxylic acids, whereas stronger reducing agents (LiAlH 4 ) immediately reduce the ...
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 ...
The bond order itself is the number of electron pairs (covalent bonds) between two atoms. [3] For example, in diatomic nitrogen N≡N, the bond order between the two nitrogen atoms is 3 (triple bond). In acetylene H–C≡C–H, the bond order between the two carbon atoms is also 3, and the C–H bond order is 1 (single bond).
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]
The intermediate imine can be isolated or reacted in-situ with a suitable reducing agent (e.g., sodium borohydride) to produce the amine product. [2] Intramolecular reductive amination can also occur to afford a cyclic amine product if the amine and carbonyl are on the same molecule of starting material. [4]
Carbonyl reduction, the net addition of H 2 across a carbon-oxygen double bond, is an important way to prepare alcohols. Stoichiometric reducing agents to accomplish this task include lithium aluminium hydride, sodium borohydride, alkoxy borohydrides, alkoxy aluminium hydrides, and boranes
In hydroboration, alkenes insert into borane B-H bonds, with anti-Markovnikov stereochemistry. Hydroboration occurs stereospecifically syn — on the same alkene face. The transition state for this concerted reaction can be visualized as a square with the corners occupied by carbon, carbon, hydrogen and boron, maximizing overlap between the ...