Ball-and-stick model of the tetrahydroborate anion, [BH4]−
Borohydride refers to the anion [BH4]−, which is also called tetrahydridoborate, and its salts.[1] Borohydride or hydroborate is also the term used for compounds containing [BH4−nXn]−, where n is an integer from 0 to 3, for example cyanoborohydride or cyanotrihydroborate [BH3(CN)]− and triethylborohydride or triethylhydroborate [BH(CH2CH3)3]−. Borohydrides find wide use as reducing agents in organic synthesis. The most important borohydrides are lithium borohydride and sodium borohydride, but other salts are well known (see Table).[2] Tetrahydroborates are also of academic and industrial interest in inorganic chemistry.[3]
^"Tetrahydroborate". Chemspider.com. Retrieved 26 February 2013.
^Rittmeyer, P.; Wietelmann, U. "Hydrides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_199. ISBN 978-3527306732.
^Makhaev, V. D. (2000). "Borohydride". Russ. Chem. Rev. (69): 727–746. doi:10.1070/RC2000v069n09ABEH000580.
Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula NaBH4 (sometimes written...
Borohydride refers to the anion [BH4]−, which is also called tetrahydridoborate, and its salts. Borohydride or hydroborate is also the term used for compounds...
Lithium borohydride (LiBH4) is a borohydride and known in organic synthesis as a reducing agent for esters. Although less common than the related sodium...
Unlike most other metal–borohydrides, which are ionic structures, aluminium borohydride is a covalent compound. Aluminium borohydride is formed by the reaction...
nonreactive with certain molten salts such as lithium fluoride, lithium borohydride, and sodium hydride. With a molar mass of 7.95 g/mol, it is the lightest...
Beryllium borohydride is an inorganic compound with the chemical formula Be[BH4]2. Beryllium borohydride is formed by the reaction of beryllium hydride...
Uranium borohydride is the inorganic compound with the empirical formula U(BH4)4. Two polymeric forms are known, as well as a monomeric derivative that...
other borohydrides, it is used as a reducing agent in organic synthesis. This colourless salt is prepared by protonolysis of sodium borohydride with acetic...
Direct borohydride fuel cells (DBFCs) are a subcategory of alkaline fuel cells which are directly fed by sodium borohydride or potassium borohydride as a...
Alternatively, a small amount of diborane product can be added to form lithium borohydride, which will decompose the fluoroborate and make the reaction autocatalytic...
in vacuum. Although not performed industrially, hydrolysis of sodium borohydride Na[BH4] with a suitable catalyst gives sodium metaborate and hydrogen...
be isolated and reduced with a suitable reducing agent (e.g., sodium borohydride) to produce the final amine product. Intramolecular reductive amination...
mild hydride-reducing agents, such as sodium borohydride, potassium borohydride, and lithium borohydride to dihydroartemisinin (a lactol) in over 90%...
For example, Na[BH3(CN)] is less reducing than its counterpart sodium borohydride, containing [BH4]−. Sodium cyanoborohydride is a mild reducing agent...
ketones to allylic alcohols. The active reductant is described as "cerium borohydride", which is generated in situ from NaBH4 and CeCl3(H2O)7. The Luche reduction...
reacting with sulfur, phosphorus, phosphorus halides, and potassium borohydride. It dissolves exothermically in water to form dark-green solutions that...
Reitz AB (April 2004). "Reductive aminations of carbonyl compounds with borohydride and borane reducing agents". Organic Reactions. 59. Hoboken, New Jersey...
by controlled potential reduction, or chemical reduction using sodium borohydride in alkaline solution, zinc in acetic acid, or by the action of thiols...
process (see direct borohydride fuel cell) creates hydrogen as needed, but has other issues, such as the high price of the sodium borohydride that is the raw...
reagents. Prominent among these reagents are the alkali metal salts of borohydrides and aluminium hydrides. In terms of reaction mechanism, metal hydrides...
wool, either as gas or from solutions of sodium dithionite, and sodium borohydride. Bleaches generally react with many other organic substances besides...
be produced in the laboratory by reducing cyanocobalamin with sodium borohydride in alkaline solution, followed by the addition of methyl iodide. This...
with a green flame. It is an intermediate in the preparation of sodium borohydride and is a popular reagent in organic chemistry. It is a weak Lewis acid...
benzaldehyde and benzyl alcohol is possible using DIBAL-H, LiAlH4 or sodium borohydride. Decarboxylation to benzene may be effected by heating in quinoline in...
behave as hydrogen-atom donors and act as acids. Hydrides such as sodium borohydride, lithium aluminium hydride, diisobutylaluminium hydride (DIBAL) and super...
catalysts are typically prepared by reacting a salt of nickel with sodium borohydride. The composition and properties vary depending on the specific preparation...
the use of reducing sugars, citrate reduction, reduction via sodium borohydride, the silver mirror reaction, the polyol process, seed-mediated growth...
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