Aldehydes, but not ketones, are smoothly reduced to alcohols with sodium triacetoxyborohydride, prepared from sodium borohydride and acetic acid in benzene. Matthews2 1national laboratory of energy and geology, estrada do paco do lumiar 22, 1649038, lisbon, portugal. Ungraded products supplied by spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use. H from the reaction of solid nabh 4 with glacial acetic. This colourless salt is prepared by protonolysis of sodium borohydride with acetic acid. Sodium borohydride is a white to grayish crystalline powder.
Review of chemical processes for the synthesis of sodium. A study of solvents for sodium borohydride and the effect of solvent. No component of this product, present at levels greater than or equal to. Sodium triacetoxyborohydride stab is a mild reducing agent that is commonly used in reductive aminations. High purity, submicron and nanopowder forms may be considered. Sciencemadness discussion board solvents for sodium. Reductiveaminationofaldehydesandketoneswithsodium triacetoxyborohydride. Reductive amination of aldehydes and ketones with sodium. Sodium borohydride is an odorless white to graywhite microcrystalline powder that often forms lumps. Triacetoxyborohydride sodium salt 56553607 suppliers. Synthesis of a histamine h3 receptor antagonistmanipulation of hydroxyproline stereochemistry, desymmetrization of homopiperazine, and nonextractive sodium triacetoxyborohydride. The information given is designed only as a guidance for safe handling, use, processing, storage, transportation, disposal and release and is not to be considered a warranty or quality specification.
The number of electrons in each of sodium s shells is 2, 8, 1 and its electron configuration is ne 3s 1. We selected sodium triacetoxyborohydride nabhoac3,4 a very mild and selective reducing agent. Nabh4 is sometimes used to reduce esters to alcohols but the reaction is generally slow. Safety data sheet according to 29cfr19101200 and ghs rev. However, the onset temperature for libh4 decomposition is 653 k and only half of. Dma is more thermally stable than dmf as a solvent for nabh4 based on consideration of the decomposition onset temperature and sensitivity to. Why sodium cyanoborohydride reactivity depends on ph. Ft05777c sodium cyanoborohydride and sodium borohydride. Kinetics of sodium borohydride hydrolysis in aqueousbasic. Sodium triacetoxyborohydride revision date mar2018 eye contact rinse immediately with plenty of water, also under the eyelids, for at least 15 minutes. The reason thf or sometimes tbutanol is used with sodium borohydride methanol is a practical one. For instance, sodium borohydride nabh4 contains 10. Sodium triacetoxyborohydride cas 56553607 appearance. Find msds or sds, a coa, data sheets and more information.
Naac3bh sodium cyanoborohydrie is a mild reducing agent useful for many reductive amination reactions but having the disadvantage of toxicity and a bit of bother to prepare. In a reductive animation, why are benzylamide, sod. Read 4 answers by scientists with 3 recommendations from their colleagues to the question asked by subhas chandra pan on nov 3, 2016. Reductive amination of ferrocenecarbaldehyde with several primary and secondary amines in the presence of sodium triacetoxyborohydride was studied. Sodium borohydride is soluble in protic solvents such as water and lower alcohols.
Sodium triacetoxyborohydride gribble major reference. Nabh4 reacts very rapidly with methanol and thus using methanol as a single solvent often requires large excesses of borohydride because of the rapid decomposition. In case of more serious fires, also alcoholresistant foam and water spray. The information provided in this safety data sheet is correct to the best of our knowledge, information and belief at the date of its publication. See table 2 sodium tetrahydridoborate, sodium borohydride, sodium.
Sodium triacetoxyborohydride solubilityies reacts with water. The thermal decomposition of sodium bisulfate to produce sodium disulfate and water. The thermal hazards associated with the original procedure to produce sodium triacetoxyborohydride stab from the reaction of nabh 4 with glacial acetic acid were. Reductions with sodium borohydridesulfur nabh 2 s 3 pdf reductions with alkyloxyaluminohydrides, redal etc. Procedures for using this mild and selective reagent have. In addition to its superior ability in effecting reductive amination of. The present research systematically investigated, for the first time, the transformation of sodium bicarbonate and co 2 into sodium formate over a series of ni based metal nanoparticles nps. Sodium triacetoxyborohydride is presented as a general reducing agent for the reductive amination of aldehydes and ketones. Selective reduction of aldehydes with sodium triacetoxyborohydride by g.
Reductive amination reductive amination is a powerful and reliable strategy for the formation of cn bonds, and can avoid the problem of overalkylation that often accompanies direct alkylation of amines with alkyl halides. Reductive amination of aldehydes and ketones by using sodium. Search results for sodium triacetoxyborohydride at sigmaaldrich. American elements produces to many standard grades when applicable, including mil spec military grade. Draw the product for the reaction below involving the. Selective reduction of aldehydes with sodium triacetoxyborohydride.
Sodium triacetoxyborohydride naoac 3 bh, abbreviated as stabh is a versatile reagent in organic synthesis. The heat of this reaction may be sufficient to ignite the hydrogen. The boronhydrogen bond is stabilized by the steric and electronwithdrawing effects of the acetoxy groups, making sodium triacetoxyborohydride a mild reducing agent. The rechargeable moltensodium systems work at approx. Request pdf stability and decomposition of nabh4 we investigate the. Procedures for using this mild and selective reagent have been developed for a wide variety of substrates. Thermal decomposition can lead to release of irritating. Sodium cyanoborohydride is especially suitable for reductive aminations. Sodium borohydride nabh4 is a mild reducing agent that is typically used to reduce aldehydes and ketones to their respective alcohols. In addition to its superior ability in effecting reductive amination of aldehydes and ketones, it can reduce nheterocycles indoles, quinolines, and isoquinolines, imines, enamines, oximes, amides, aryl ketones, acetals, and other.
Safety data sheet sodium triacetoxyborohydride date prepared. Oac 3 and the related tetramethylammonium triacetoxyborohydride are commercially available as colorless powders. Why are benzylamine, sodium triacetoxyborohydride, and acetic acid used in excess relative to methyl or ethyl pyruvate. It is preferred to sodium cyanoborohydride nabh3cn in many applications due to reduced toxicity of the. Selective reduction of aldehydes with sodium triacetoxyborohydride g.
Sodium borohydride nabh4 or bh4na cid 4311764 structure, chemical names, physical. An efficient, optimized synthesis of fentanyl and related. Acetic acid may be used as catalyst with ketone reactions. It converts aldehydes chemoselective, ketones stereoselective to the corresponding alcohols in the manufacture of pharmaceuticals and other fine chemicals. Sodium triacetoxyborohydride i want to do a reductive amination with sodium triacetoxyborohydride between aniline and a ketone with dcm as solvent. Sodium borohydride is rapidly decomposed to release hydrogen gas when contacted with acid so it cannot reduce the acid alone and should be used in. Ac291820000, ac291820250, ac29182, ac291825000 synonyms. Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, is a chemical compound used as a reducing agent in organic synthesis. Sodium triacetoxyborohydride 56553607 msds report, sodium triacetoxyborohydride msds safety technical specifications search, sodium triacetoxyborohydride safety information specifications ect. Triacetoxyborohydride is a safer reducing agent than sodium cyanoborohydride with comparable reactivity. We therefore decided to explore the oxidationreduction approach, although past experience suggested that nabh4 reduction of both 7 and 16keto groups would sterically favor the retention products, 7a and 165alcohols. Sodium triacetoxyborohydride nabh oac3 is particularly effective in reductive aminations due to its large scope, mildness, and selectivity. Like other borohydrides, it is used as a reducing agent in organic synthesis.
Sodium triacetoxyborohydride, nabhoac3, produced in situ from nabh4 and three equivalents of acetic acid, exhibits such a weakening of reducing power that aldehydes are selectively reduced without ketones being affected 53. Preparation from sodium borohydride in situ prior to reduction is our preferred method. Safety data sheet creation date 29jan2010 revision date 17jan2018 revision number 4 1. An excess of nabh4 can be used to compensate for the decomposition. Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated stab, is a chemical compound with the formula nach 3 coo 3 bh. This colourless salt is prepared by protonolysis of sodium. Ungraded products supplied by tci america are generally suitable for common industrial uses.
H a detailed study of the process for in situ production of stab. This reaction takes place at a temperature of 250230c. Your new online msds binder is a place for you to store the material safety data sheets you need to deploy. Since the reaction rate for the reduction of iminium ions is. Callery, llc offers reducing agents including sodium triacetoxyborohydride. Sodium triacetoxyborohydride 56553607 nmr spectrum, sodium triacetoxyborohydride hnmr spectral analysis, sodium triacetoxyborohydride cnmr spectral analysis ect. Which is better to use, product 316393, sodium triacetoxyborohydride, or sodium cyanoborohydride. Sodium cyanoborohydride, sodium cyanotrihydroborate. Sodium triacetoxyborohydride is used as a reagent in reductive amination of ketones, aldehydes and lactamization of carbonyl compounds with amines. Very interesting information on nabh4, hive methods. Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated stab, is a chemical compound with the formula nach3coo3bh.
Ni nps and eight nim m stands for a second metal nps were prepared by a facile wet chemical process and then their catalytic performance were evaluated in sodium. This white solid, usually encountered as a powder, is a reducing agent that finds application in chemistry, both in the laboratory and on an industrial scale. It is used in the reductive alkylation of amines, novel metals and oximes. Organometallic substance, solid, waterreactive, flammable contains. Optical grade, usp and epbp european pharmacopoeiabritish. Sodium triacetoxyborohydride is a general, mild, and selective reducing agent for the reductive amination of various aldehydes and ketones.
This method was used for the synthesis of new ferrocenylmethylamines, viz. Sigmaaldrich offers a number of sodium triacetoxyborohydride products. Safety data sheet 112030 sodium triacetoxyborohydride. It also reacts with these protic solvents to produce h 2, however, these reactions are fairly slow complete decomposition. In a reductive animation, why are benzylamide, sodium triacetoxyborohydride. Structure, properties, spectra, suppliers and links for. Sodium triacetoxyborohydride,and acetic acid used in excess relative to methyl pyrivate.
Sciencemadness discussion board sodium borohydride to. Sodium triacetoxyborohydride 56553607 msds, safety. The company operates in more than 30 countries and delivers an extensive portfolio of products and services. Stability and decomposition of nabh4 request pdf researchgate. Pdf selective reduction of aldehydes with sodium triacetoxyborohydride. Sodium triacetoxyborohydride sodium triacetoxyborohydride is very likely to work. Sodium triacetoxyborohydride wikimili, the free encyclopedia. Sciencemadness discussion board naac3bh powered by xmb. Identification product name sodium borohydride cat no. Kinetics of sodium borohydride hydrolysis in aqueousbasic solutions rajasree retnamma1, c.
It is rather surprising that this synthesis works at all, as the decomposition. Hydrogen production from solid sodium borohydride with hydrogen. Reductive amination involves a one or twostep procedure in which an amine and a carbonyl. Very interesting information on nabh4, hive methods discourse. Alfa aesar sodium triacetoxyborohydride, 95% fisher. Commercially practiced sodium borohydride synthesis process. Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula na bh 4. Sodium borohydride and boron trifluoride in diglyme or thf yield diborane. Recent advances in the use of sodium borohydride as a. Safety evaluation of sodium borohydride in dimethylacetamide.
A safe process for production of sodium triacetoxyborohydride stab. Sodium triacetoxyborohydride 56553607 s1476 spectrum. Asian journal of organic chemistry 2015, 4 4, 333336. Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated stab, is a chemical compound with the formula na ch 3 coo 3 bh.
Transformation of sodium bicarbonate and co2 into sodium. Identification of the substancemixture and of the companyundertaking. Sodium triacetohydroborate, triacetohydroborate sodium salt. Ionpaircatalyzed sodium borohydride reduction in aprotic organic solvents. Sodium triacetoxyborohydride safety data sheet page 1 8 creation date 16jan2015 revision date mar2018 version 1. Reductive amination chem 115 with care to maintain a ph of 67, a mixture of a ketone or aldehyde reactant, an amine, and sodium. Studiesondirectandindirectreductive aminationprocedures1 ahmedf. Stab has the advantage over sodium cyanoborohydride nabh3cn of not producing toxic sidepdts. Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, is used as a reducing agent in organic synthesis. Sodium triacetoxyborohydride organic chemistry portal. It is decomposed by water to form sodium hydroxide, a corrosive material, and hydrogen, a flammable gas. One reagent lane fair lawn, nj 07410 for information in north america, call.
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