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Chemical compound
Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula NaBH4 (sometimes written
Sodium_borohydride
Chemical compound
other borohydrides, it is used as a reducing agent in organic synthesis. This colourless salt is prepared by protonolysis of sodium borohydride with acetic
Sodium_triacetoxyborohydride
Chemical compound
Na[BH3(CN)] is less reducing than its counterpart sodium borohydride, containing [BH4]−. Sodium cyanoborohydride is a mild reducing agent. It is generally
Sodium_cyanoborohydride
Any chemical compound having a borohydride anion
Borohydrides find wide use as reducing agents in organic synthesis. The most important borohydrides are lithium borohydride and sodium borohydride, but
Borohydride
Chemical compound
not performed industrially, hydrolysis of sodium borohydride Na[BH4] with a suitable catalyst gives sodium metaborate and hydrogen gas: Na[BH4] + 2 H2O
Sodium_metaborate
Ultrafine particles of silver between 1 nm and 100 nm in size
including the use of reducing sugars, citrate reduction, reduction via sodium borohydride, the silver mirror reaction, the polyol process, seed-mediated growth
Silver_nanoparticle
Chemical compound
Lithium borohydride (LiBH4) is a borohydride and known in organic synthesis as a reducing agent for esters. Although less common than the related sodium borohydride
Lithium_borohydride
Conversion of a carbonyl to an amine
isolated or reacted in-situ with a suitable reducing agent (e.g., sodium borohydride) to produce the amine product. Intramolecular reductive amination
Reductive_amination
Chemical compound
with the formula KBH4. It can be obtained through the reaction of sodium borohydride with aqueous potassium hydroxide in a methanol or water solvent: NaBH4
Potassium_borohydride
Subcategory of alkaline fuel cells
Direct borohydride fuel cells (DBFCs) are a subcategory of alkaline fuel cells which are directly fed by sodium borohydride or potassium borohydride as a
Direct_borohydride_fuel_cell
Chemical element with atomic number 5 (B)
the boranes. Sodium borohydride is obtained by hydrogenation of trimethylborate: B(OCH3)3 + 4 Na + 2H2 → NaBH4 + 3 NaOCH3 Sodium borohydride is a white
Boron
Catalyst composed of nickel and boron
led by Hermann I. Schlesinger, discoverer of borohydrides. They noted that reaction ofSodium borohydride NaBH 4 with salts of certain transition metals
Nickel_boride_catalyst
Chemicals used to whiten or disinfect
used to bleach wool, either as gas or from solutions of sodium dithionite, and sodium borohydride. Bleaches generally react with many other organic substances
Bleach
American chemist (1912–2004)
separate the two products, it was discovered that sodium borohydride reduced the acetone. Sodium borohydride is a mild reducing agent that works well in reducing
Herbert_C._Brown
Boron compound, a salt of boric acid
formulations). Borax bead test John Veatch List of cleaning agents Sodium borohydride Ulexite It is also written as Na2B4O7·10H2O, which shows that it is
Borax
Chemical compound
reaction between sodium borohydride and an ammonium salt: (NH4)2SO4 + 2 NaBH4 → BH3·NH3 + Na2SO4 + 2 H2 The initially formed ammonium borohydride [NH4]+[BH4]−
Ammonia_borane
Chemical element with atomic number 11 (Na)
reaction) in organic chemistry. Metallic sodium is used mainly for the production of sodium borohydride, sodium azide, indigo, and triphenylphosphine. A
Sodium
Drug used to treat malaria
with mild hydride-reducing agents, such as sodium borohydride, potassium borohydride, and lithium borohydride to dihydroartemisinin (a lactol) in over 90%
Dihydroartemisinin
Organic reduction of any carbonyl group by a reducing agent
nucleophilic and better reducing agents relative to borohydrides. The relatively weak reducer sodium borohydride is typically used for reducing ketones and aldehydes
Carbonyl_reduction
Chemical compound
as a reducing agent. It is more powerful than the related reagent sodium borohydride owing to the weaker Al-H bond compared to the B-H bond. Often as a
Lithium_aluminium_hydride
Chemical compound
compound. Aluminium borohydride is formed by the reaction between sodium borohydride with aluminium chloride: 3 NaBH4 + AlCl3 → Al(BH4)3 + 3 NaCl or as
Aluminium_borohydride
Chemical compound
lithium aluminium hydride or from boron trifluoride ether solution with sodium borohydride. Both methods result in as much as 30% yield: 4 BCl3 + 3 LiAlH4 →
Diborane
Chemical compound
burns 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
Trimethyl_borate
Organic compound (C6H5COOH)
benzaldehyde and benzyl alcohol is possible using DIBAL-H, LiAlH4 or sodium borohydride. Decarboxylation to benzene may be effected by heating in quinoline
Benzoic_acid
Chemical compound
require sodium borohydride as a stabilizer, which could result in undesired side reactions. In contrast, BH3·THF requires sodium borohydride to inhibit
Borane_dimethylsulfide
Chemical compound
used in the reduction of carboxylic acids to primary alcohols with sodium borohydride (NaBH4). Its use raises safety concerns since the carcinogenic compound
BOP_reagent
Molecule with a hydrogen bound to a more electropositive element or group
behave as hydrogen-atom donors and act as acids. Hydrides such as sodium borohydride, lithium aluminium hydride, diisobutylaluminium hydride (DIBAL) and
Hydride
Chemical compound
process: 2 SO2 + Zn → ZnS2O4 ZnS2O4 + 2 NaOH → Na2S2O4 + Zn(OH)2 The sodium borohydride method obeys the following stoichiometry: NaBH4 + 8 NaOH + 8 SO2 →
Sodium_dithionite
Chemical compound
diborane in THF. Alternatively, it can be prepared by the oxidation of sodium borohydride with iodine in THF. The complex can reduce carboxylic acids to alcohols
Borane–tetrahydrofuran
Chemical compound
Sodium hydride is the chemical compound with the empirical formula NaH. This alkali metal hydride is primarily used as a strong yet combustible base in
Sodium_hydride
Chemical compound
reducing agents commonly include lithium aluminium hydride (LAH), sodium borohydride, aluminum amalgam or Raney nickel are used in suitable solvents like
Phenyl-2-nitropropene
Motor vehicle
cell using hydrogen produced by a sodium borohydride reformer inside the car. Because the reactant (sodium borohydride, NaBH4) contained no carbon, the
Chrysler_Natrium
Chemical compound
60 °C. Uranium borohydride was discovered by Hermann Irving Schlesinger and Herbert C. Brown, who also discovered sodium borohydride. Uranium hexafluoride
Uranium_borohydride
Age-related process of deterioration occurring on paper products
documents can be repaired, with greater or lesser success, using sodium borohydride, proprietary bleaches, dilute hydrogen peroxide or lasers. Each method
Foxing
Chemical compound
of sodium molybdate, conductivity is kept at a minimum and thus galvanic corrosion potentials are decreased. When treated with sodium borohydride, molybdate
Sodium_molybdate
High-strength glass, made of silica and boron trioxide
optical clarity, but the glass can react with sodium hydride upon heating to produce sodium borohydride, a common laboratory reducing agent. Fused quartz
Borosilicate_glass
Chemical compound
for a nickel-boron catalyst obtained by reacting nickel salts with sodium borohydride. However, that product is not a well-defined compound, and its bulk
Dinickel_boride
Form of vitamin B12
can be produced in the laboratory by reducing cyanocobalamin with sodium borohydride in alkaline solution, followed by the addition of methyl iodide. This
Methylcobalamin
Chemical compound
the carbonyl group only to provide carveol (5); a combination of sodium borohydride and CeCl3 (Luche reduction) is also effective. Hydrazine and potassium
Carvone
Chemical compound
tetraoctylammonium bromide where it is then reduced with aqueous sodium borohydride in the presence of a thiol. Chloroauric acid is the precursor used
Chloroauric_acid
Chemical synthesis
investigated. Finally, the newly formed double bond was reduced by sodium borohydride to indoline 9, with the C8 hydrogen atom approaching from the least
Strychnine_total_synthesis
Chemical species that donates an electron to another species in a redox reaction
catalyst Sodium amalgam (Na(Hg)) Sodium-lead alloy (Na + Pb) Zinc amalgam (Zn(Hg)) (reagent for Clemmensen reduction) Diborane Sodium borohydride (Na BH4)
Reducing_agent
Study of compounds containing a boron-carbon bond
borate, debatably not an organoboron compound, is an intermediate in sodium borohydride production. Boranes and borinic, boronic, and borate esters all form
Organoboron_chemistry
Chemical compound
herbicide sold under the name Assert. The reduction of quinoline with sodium borohydride in the presence of acetic acid produces kairoline A. Several anti-malarial
Quinoline
Mineral (hydrated sodium calcium borate hydroxide)
hydrogen as a fuel for cars has come to the forefront. The compound sodium borohydride (NaBH4) is currently being considered as an excellent hydrogen storage
Ulexite
Collection of bound atoms or molecules
nanoclusters. Some examples of chemical reductants are sodium borohydride (NaBH4) and sodium hypophosphite (NaPO2H2.H2O). For instance, Dickson and his
Nanocluster
Chemical compound
solution as the water evaporates in air. Sodium tetrahydroxyborate is end product of the hydrolysis of sodium borohydride Na[BH4] at 45–65 °C, through the formation
Sodium_tetrahydroxyborate
of molten methimazole (1-methylimidazole-2-thione) with sodium borohydride, giving the sodium salt of the ligand. Salts of the TmMe anion are known also
Tm_ligands
Stimulant alkaloid responsible for mouth cancers
[13221-89-1] (4). The reduction of the ketone group with sodium borohydride gave N-Methyl-3-carbomethoxy-4-hydroxypiperidine, PC3029557 (5). Reaction
Arecoline
Reduction of ketones and aldehydes to their corresponding alcohols
reductions have been described as "obsolete" owing to the development of sodium borohydride and related reagents. The MPV reduction was independently discovered
Meerwein–Ponndorf–Verley reduction
Meerwein–Ponndorf–Verley_reduction
Psychedelic drug
formaldehyde followed by reduction with sodium cyanoborohydride or sodium triacetoxyborohydride. Sodium borohydride can be used but requires a larger excess
Dimethyltryptamine
Cyclic carboxylic ester
ring-opening and finally reduction of the aldehyde to the alcohol with sodium borohydride and intramolecular lactone formation Organic Syntheses, Coll. Vol
Lactone
Chemical compound
250 °C. This catalyst is produced by reduction of nickel salts with sodium borohydride. Trinickel boride can be obtained also by compressing nickel and boron
Trinickel_boride
Chemical compound
agent than sodium borohydride due to the weaker and more polar Al-H bond compared to the B-H bond. Like LAH, it reduces esters to alcohols. Sodium aluminium
Sodium_aluminium_hydride
Methods of storing hydrogen for later use
hydrogen storage densities. Leading candidates are lithium hydride, sodium borohydride, lithium aluminium hydride and ammonia borane. A French company McPhy
Hydrogen_storage
Chemical-induced nickel coating of a surface
a patent for a general class of processes using sodium borohydride, dimethylamine borane, or sodium hypophosphite, in the presence of thallium salts
Electroless nickel-phosphorus plating
Electroless_nickel-phosphorus_plating
Chemical compound
synthesis, first, hydrazoic acid and sodium borohydride is reacted in diethyl ether at -78 °C to produce sodium tetraazidoborate (which decomposes at
Pentazenium_tetraazidoborate
Chemical reaction
accomplish this task include lithium aluminium hydride, sodium borohydride, alkoxy borohydrides, alkoxy aluminium hydrides, and boranes. Although stoichiometric
Enantioselective reduction of ketones
Enantioselective_reduction_of_ketones
Boron compound
2 B3H6N3 + 12 H2 An alternative more efficient route begins with sodium borohydride and ammonium sulfate: 6 NaBH4 + 3 (NH4)2SO4 → 2 B3N3H6 + 3 Na2SO4
Borazine
Chemical compound
two-step process that illustrates the reduction of carbonyls using sodium borohydride and the dehydration of alcohols: 4 C6H5C(O)CH3 + NaBH4 + 4 H2O → 4
Acetophenone
Organic compound containing the functional group R–CH=O
Stoichiometric reductions are also popular, as can be effected with sodium borohydride. The formyl group readily oxidizes to the corresponding carboxyl group
Aldehyde
Organism not requiring oxygen for its growth
achieves an anaerobic environment by the reaction of water with sodium borohydride and sodium bicarbonate tablets, which produce hydrogen gas and carbon dioxide
Anaerobic_organism
anhydrous hydrogen chloride) Sulfuric acid Methyl isobutyl ketone (MIBK) Sodium permanganate All listed chemicals as specified in 21 CFR 1310.02 (a) or
DEA_list_of_chemicals
Rule in organic chemistry
of reserpine. The subsequent imine intermediate was treated with sodium borohydride, affording the wrong stereoisomer due to the Fürst–Plattner effect
Fürst–Plattner_rule
Chemical reaction of an alkene with mercuric acetate to form an alcohol
created by the oxymercuration reaction is almost always treated with sodium borohydride (NaBH4) in aqueous base in a reaction called demercuration. In demercuration
Oxymercuration_reaction
Organomolybdenum compound
is prepared by combining molybdenum pentachloride, sodium cyclopentadienide, and sodium borohydride. The dihydride converts to molybdocene dichloride upon
Molybdocene_dihydride
Cleavage of C=C, C≡C, or N=N bonds with ozone
dimethyl sulfide produces aldehydes or ketones. While the use of sodium borohydride produces alcohols. (R group can also be hydrogens) The use of hydrogen
Ozonolysis
Organic synthesis
orthoformate and boron trifluoride) and then ketone reduction with sodium borohydride produce an intermediate from which many monosaccharides can be synthesised
Achmatowicz_reaction
Chemical compound
compound is prepared by the reaction of tert-butylammonium chloride and sodium borohydride: t-BuNH3Cl + NaBH4 → t-BuNH2BH3 + H2 + NaCl In organic synthesis,
Borane_tert-butylamine
Form of vitamin B-12
cyanocobalamin by controlled potential reduction, or chemical reduction using sodium borohydride in alkaline solution, zinc in acetic acid, or by the action of thiols
Cyanocobalamin
Chemical element with atomic number 45 (Rh)
Prize-winning route to the chiral drug L-DOPA. When treated with sodium borohydride and carbon monoxide, RhCl(P(C6H5)3)3 converts to the pentacoordinate
Rhodium
Chemical compound
sodium borohydride, potassium borohydride, lithium borohydride, lithium aluminium hydride, sodium aluminium hydride. The reaction with borohydrides is
Germane
Type of refractory ceramics
and V metal diboride nanocrystals via borothermal reduction with sodium borohydride". Journal of the American Ceramic Society. 101 (6): 2627–2637. doi:10
Ultra-high temperature ceramic
Ultra-high_temperature_ceramic
Chemical compound
multiple steps: N-methylation with methyl iodide, organic reduction with sodium borohydride, and finally hydrolysis with mercury(II) chloride in water. Alkylation
Thiazole
Type of rocket engine fuel
its derivatives. Triethylene glycol dimethyl ether (Triglyme) and Sodium borohydride (8 wt%) + Hydrogen Peroxide has been tested as a green hypergolic
Hypergolic_propellant
Chemical compound
(+)-camphor gives (−)-isoborneol and (+)-borneol. Reduction of camphor with sodium borohydride (fast and irreversible) gives instead the diastereomer isoborneol
Borneol
– NaHSO4 Sodium bisulfite – NaHSO3 Sodium borate – Na2B4O7 Sodium borohydride – NaBH4 Sodium bromate – NaBrO3 Sodium bromide – NaBr Sodium bromite –
List_of_inorganic_compounds
Toxic, waxy organic compound
isoborneol using sodium borohydride. It can be converted to the alkene bornylene. Camphor forms an enolate when treated with sodium hydride. The enolate
Camphor
Chemical element with atomic number 51 (Sb)
be produced by treating Sb3+ salts with hydride reagents such as sodium borohydride. Stibine decomposes spontaneously at room temperature. Because stibine
Antimony
Suspension of gold nanoparticles in a liquid
themselves, the synthesis of them involves chemicals that are hazardous. Sodium borohydride, a harsh reagent, is used to reduce the gold ions to gold metal. The
Colloidal_gold
Compound derived from an acid
used to reduce esters to two primary alcohols. The related reagent sodium borohydride is slow in this reaction. DIBAH reduces esters to aldehydes. Direct
Ester
Plating process
metal cation. Common reducing agents include formaldehyde, sodium borohydride, glucose, sodium hypophosphite, hydrogen peroxide, and ascorbic acid. Other
Electroless_deposition
Chemical compound
the cyclization with good yield. The ketone is then reduced with sodium borohydride yielding a benzyl alcohol. Condensation with 4-hydroxycoumarin under
Brodifacoum
Functional group with the chemical structure R–S–S–R′
reagents, and a common laboratory demonstration "uncooks" eggs with sodium borohydride. Alkali metals effect the same reaction more aggressively: RS−SR +
Disulfide
Organic reduction
to amines include lithium aluminium hydride, lithium borohydride, diborane, or elemental sodium in alcohol solvents. Nitriles can also be converted to
Nitrile_reduction
Chemical compound containing the functional group R3NO
with Raney nickel; or acidic hydride salts (e.g. a combination of sodium borohydride and aluminum trichloride). In very rare cases, simply standing in
Amine_oxide
Chemical compound
OsH2(CO)[P(C6H5)3]3 With ethanol and sodium borohydride they react to produce OsH4[P(C6H5)3]3. Na2OsCl6•6H2O + 3(C6H5)3P borohydride ————→ OsH4[P(C6H5)3]3 With
Sodium_hexachloroosmate
Hypothetical vehicle deriving energy from water
are not precluded by the laws of nature. Aluminium, magnesium, and sodium borohydride react with water to generate hydrogen and have been used in hydrogen
Water-fuelled_car
Chemical production of a pharmaceutical drug
starting materials pyridine and acrolein. Pyridine (1) is reduced with sodium borohydride in presence of benzyl chloroformate to the Cbz protected dihydropyridine
Oseltamivir_total_synthesis
resolved. Commonly, borohydride complexes are prepared by salt metathesis reactions using potassium borohydride or sodium borohydride: CuCl(PMePh2)3 + NaBH4
Metal complexes of borohydride
Metal_complexes_of_borohydride
Chemical compound
(S)-1-pyrroline-5-carboxylic acid Reduction of glutamic acid semialdehyde with sodium borohydride gives hydroxyaminovaleric acid. Glutamate-1-semialdehyde Baich A (1971)
Glutamate-5-semialdehyde
Organic compound or functional group containing a C=N bond
m-tolylbenzylamine: Other reducing agents are lithium aluminium hydride and sodium borohydride. The asymmetric reduction of imines has been achieved by hydrosilylation
Imine
Chemical compound
agent sodium triethylborohydride is commercially available as toluene solutions. LiBHEt3 is a stronger reducing agent than lithium borohydride and lithium
Lithium_triethylborohydride
American inorganic chemist (1882–1960)
Herbert C. Brown discovered sodium borohydride in 1940 and both were involved in the further development of borohydride chemistry. Schlesinger studied
Hermann_Irving_Schlesinger
Chemical compound
C6H5S-SC6H5 + 2 H2O The disulfide can be reduced back the thiol using sodium borohydride followed by acidification. This redox reaction is also exploited in
Thiophenol
Alkaloid
finally converted to racemic N-methylphenylethanolamine by means of sodium borohydride in ethanol. An efficient, stereospecific synthesis of halostachine
Halostachine
Chemical compound
dehydrohalogenation reaction with DMF Luche reduction to alcohol with sodium borohydride elimination reaction with Burgess reagent oxidation with p-chloranil
Azulene
Chemical compound
is reduced to antimony metal. With other reducing agents such as sodium borohydride or lithium aluminium hydride, the unstable and very toxic gas stibine
Antimony_trioxide
Organic compound with at least one hydroxyl (–OH) group
Nozaki–Hiyama–Kishi reaction. Aldehydes or ketones are reduced with sodium borohydride or lithium aluminium hydride (after an acidic workup). Another reduction
Alcohol_(chemistry)
Dissociation of molecules by ionizing radiation
energy source for regeneration of spent fuel by converting sodium borate into sodium borohydride, preventing it from reacting with other products. By applying
Radiolysis
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