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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 ...
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 ...
Sodium borohydride: a versatile reducing agent; converts ketones and aldehydes to alcohols Sodium chlorite: in organic synthesis, used for the oxidation of aldehydes to carboxylic acids Sodium hydride: a strong base used in organic synthesis Sodium hydroxide
They discovered that sodium hydride and methyl borate reacted to produce sodium trimethoxyborohydride, which was viable as a substitute for the lithium hydride. [12] Soon they were informed that there was no longer a need for uranium borohydride, but it appeared that sodium borohydride could be useful in generating hydrogen. They began to look ...
Stoichiometric reducing agents to accomplish this task include lithium aluminium hydride, sodium borohydride, alkoxy borohydrides, alkoxy aluminium hydrides, and boranes. Although stoichiometric chiral reducing agents often afford products with high enantioselectivity, the necessity of a stoichiometric amount of chiral material is a disadvantage.
Trimethyl borate is the main precursor to sodium borohydride by its reaction with sodium hydride in the Brown-Schlesinger process: 4 NaH + B(OCH 3) 3 → NaBH 4 + 3 NaOCH 3. It is a gaseous anti-oxidant in brazing and solder flux. Otherwise, trimethyl borate has no announced commercial applications.
Hydrogenation (Adams' catalyst) gave alcohol 30, chromic acid oxidation gave ketone 31, sodium borohydride reduction stereoselectively gave alcohol 32, hydrolysis followed by acylation gave acetate 33, thionyl chloride treatment gave acyl chloride 34 and methyl cadmium the ketone 35. Cholesterol synthesis Woodward 2
The borohydride anion is susceptible to reaction with even weak acids, resulting protonolysis of one or more B-H bonds. Protonolysis of sodium borohydride with acetic acid gives triacetoxyborohydride: [1] NaBH 4 + 3 HO 2 CCH 3 → NaBH(O 2 CCH 3) 3 + 3 H 2. Related reactions occur for hydrides of other electropositive elements, e.g. lithium ...