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Borane–tetrahydrofuran is an adduct derived from borane and tetrahydrofuran (THF). These solutions, which are colorless, are used for reductions and hydroboration, reactions that are useful in synthesis of organic compounds. A common alternative to BHF•THF is borane–dimethylsulfide, which has a longer shelf life and effects similar ...
Furthermore, it is not necessary for the hydroborane to have more than one hydrogen. For example, reagents of the type R 2 BH are commonly used, where R can represents the remainder of the molecule. Such modified hydroboration reagents include 9-BBN, catecholborane, and disiamylborane.
The advantages of BMS over other borane reagents, such as borane-tetrahydrofuran, are its increased stability and higher solubility. [1] BMS is commercially available at much higher concentrations than its tetrahydrofuran counterpart (10 M ) and does not require sodium borohydride as a stabilizer , which could result in undesired side reactions ...
Borane dimethylsulfide (BMS) is a complexed borane reagent that is widely used for hydroborations. [4] Much of the original work on hydroboration employed diborane as a source of BH 3. Usually however, borane dimethylsulfide complex BH 3 S(CH 3) 2 (BMS) is used instead. [5] It can be obtained in highly concentrated forms. [6]
Solutions containing borane dimethylsulfide and borane–tetrahydrofuran are commercially available; in tetrahydrofuran a stabilising agent is added to prevent the THF from oxidising the borane. [8] A stability sequence for several common adducts of borane, estimated from spectroscopic and thermochemical data, is as follows:
It is a colorless or white liquid but is typically marketed and used as a THF solution. [2] The related reducing agent sodium triethylborohydride is commercially available as toluene solutions. LiBHEt 3 is a stronger reducing agent than lithium borohydride and lithium aluminium hydride .
Several years later in 1987, E. J. Corey and coworkers developed the reaction between chiral amino alcohols and borane (BH 3), generating oxazaborolidine products which were shown to rapidly catalyze the enantioselective reduction of achiral ketones in the presence of BH 3 •THF.
These compounds are catalysts, reagents, and synthetic intermediates. The trialkyl and triaryl derivatives feature a trigonal-planar boron center that is typically only weakly Lewis acidic. Except a few bulky derivatives, the hydrides (n = 1 or 2) dimerize, like diborane itself. Trisubstituted derivatives, e.g. triethylboron, are monomers. [5]
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