Sodium borohydride: Facts, Discussion Forum, and Encyclopedia Article

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Sodium borohydride

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	Sodium borohydride
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	Topics Sodium borohydride Topic Home Sodium borohydride, also known as sodium tetrahydroborate, has the chemical formulaChemical formula A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compoun... NaSodium Sodium is a chemical element which has the symbol Na , atomic number 11, atomic mass 22.9898 g/mol, oxidation number +1.... BBoron \|-\| colspan="6" align="center" \| Boron-10 content may be as low as 19.1% and ashigh as 20.3% in natural samples.... HHydrogen \|-\| Triple point \|\| 13.8033 K, 7.042 kPa... ₄. This white solid, usually encountered as a powder, is a specialty reducing agentReducing agent A reducing agent* is the element or a compound in a redox reaction that reduces another species.... used in the manufacture of pharmaceuticalPharmacology Overview Pharmacology is the study of how substances interact with living organisms to produce a change in function.... s and other organic and inorganic compounds. It is soluble in methanol and water, but reacts with both in the absence of base. The compound was discovered in the 1940's by H. I. SchlessingerHermann Irving Schlesinger Hermann Irving Schlesinger was an American inorganic chemist, working in boron chemistry.... , who led a team that developed metal borohydrides for wartime applications. Synthesis and handling Sodium borohydride is prepared by the reaction of sodium hydrideSodium hydride Sodium hydride is the chemical compound with the formula NaH.... on trimethylborate at 250-270°C: B(OCH₃)₃ + 4 NaH ? NaBH₄ + 3 NaOCH₃ It can also be generated by the action of NaH on powdered borosilicate glassBorosilicate glass Borosilicate glass is a particular type of glass, better known under the brand names Pyrex, Kimax, and Endural.... . NaBH₄ can be recrystallized by dissolving in warm (50 °C) diglymeDiglyme Diglyme, or bis ether, is a high boiling solvent.... followed by cooling the solution. Reactivity Organic synthetic applications Sodium borohydride reduces aldehydeAldehyde Summary An aldehyde is an organic compound containing... s and ketoneKetone A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical co... s into alcoholAlcohol In chemistry, an alcohol is any organic compound in which a hydroxyl group is bound to a carbon atom of an alkyl or substit... s, as well as the more reactive carboxylic acid derivatives acyl chlorideAcyl chloride In organic chemistry, an acyl chloride is an organic compound which is a reactive derivative of a carboxylic acid.... s and thiol esters. However, unlike the powerful reducing agent lithium aluminium hydrideFacts About Lithium aluminium hydride Lithium aluminium hydride, commonly abbreviated to LAH, is a powerful reducing agent used in organic chemistry.... , sole use of NaBH₄ with gentle reaction conditions will not reduce esterEster In chemistry, esters are organic compounds in which an organic group replaces a hydrogen atom in an oxygen acid.... s, amideAmide n chemistry, an *amide* is one of two kinds of compounds: ... s, or carboxylic acidCarboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula --OH, usua... s. An example of the use of sodium borohydride is the industrial production of fexofenadineFexofenadine Fexofenadine hydrochloride is an antihistamine drug used in the treatment of hayfever and similar allergy symptoms.... which includes a reduction step: Related reagents The activity of borohydride reducing agents can be attenuated by stabilising the boron-hydride bond. This is done through attaching sterically bulky groups or electron withdrawing groups. Acetyl (sodium triacetoxyborohydride, (NaBH(OCOCH₃)₃) or cyano) groups have been used for such a purpose. As a result, they find use in the reductive aminationReductive amination Reductive amination is a type of amination reaction which involves the conversion of a carbonyl group to an amine.... reaction. Here, the imine intermediate must be selectively reduced in the presence of the aldehyde or ketone starting material. Stronger reducing agents can be generated by destabilising the boron-hydride bond. This is found in compounds such as superhydride and L-SelectrideL-selectride L-selectride, is an organic compound.... (lithium tri-sec-butylborohydride). Other reactions Oxidation of NaBH₄ with iodineIodine Iodine , is a chemical element in the periodic table that has the symbol I and atomic number 53.... in tetrahydrofuranTetrahydrofuran Tetrahydrofuran is a heterocyclic organic compound.... creates the BH₃Diborane Diborane is the chemical compound with the formula B2H6.... -THFTetrahydrofuran Tetrahydrofuran is a heterocyclic organic compound.... complex, which can reduce esters. Likewise the NaBH₄-MeOH system, formed by the addition of methanolMethanol Methanol, also known as methyl alcohol or wood alcohol, is a chemical compound with chemical formula CH3OH.... to sodium borohydride in refluxing THF reduces esters to the corresponding alcohols for instance benzyl benzoateBenzyl benzoate Benzyl benzoate is the organic compound with the formula C6H5CH2O2CC6H5.... to benzyl alcoholBenzyl alcohol Benzyl alcohol, also known as phenylmethanol, or phenylcarbinol, is a clear, colorless liquid with a mild pleasa... . BH₄^- is an excellent ligandFacts About Ligand In chemistry, a ligand is an atom, ion, or molecule that generally donates one or more of its electrons through a coordinat... for metal ions. Such borohydride complexes are often prepared by the action of NaBH₄ (or the LiBH₄) on the corresponding metal halide, e.g. Zr(BH₄)₄. Fuel cells Sodium borohydride is also used in experimental fuel cellFuel cell A fuel cell is an electrochemical energy conversion device.... systems. As a fuel it is less flammable and less volatile than gasoline but more corrosive. It is relatively environmentally friendly because of the low toxicity of borates. The hydrogen is generated for a fuel cell by catalyticCatalyst In chemistry, a catalyst is a substance that decreases the activation energy of a chemical reaction without itself being c... decomposition of the aqueous borohydride solution: NaBH₄ + 2H₂O ? NaBO₂ + 4H₂ See also Lithium borohydrideFacts About Lithium borohydride Lithium Borohydride is known in organic synthesis as a reducing agent for esters.... External links