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Sodium Cyanoborohydride CAS 25895-60-7

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  • Appearance: White powder
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Sodium Cyanoborohydride Supplement
25895-60-7

Basic Info of Sodium Cyanoborohydride

What is Sodium Cyanoborohydride?

Sodium cyanobohydride (nabh3cn) is a discerning reductant made use of for a selection of chemical decrease, consisting of the reductive amination of aldehydes, ketones, acetals, epoxides, oximes, enamines, aldehydes as well as ketones, and the reductive alkylation of amines and also hydrazine. The stability of salt cyanobohydride under acidic conditions as well as its solubility in aprotic solvents substantially improve its use as a lowering agent. Sodium cyanobohydride is a more moderate as well as selective reductant than sodium borohydride.

Because of the electron absorption of cyano team, salt cyanobohydride is a weaker as well as even more discerning reductant than sodium borohydride. One more benefit of it is that it is stable to pH = 3 in acid and can be utilized for decrease in the presence of practical teams sensitive to the even more alkaline reduction conditions of salt borohydride.

Aldehydes and ketones are not affected by sodium cyanobohydride in neutral solution, but they are easily lowered to corresponding alcohols by protonated carbonyl at ph=3-4. By exchanging the hydrogen of borohydride right into deuterium or tritium in advance, as well as reacting with D2O or tritiated water, an efficient and also cost-effective path can be utilized for the reduction of deuterated or tritiated aldehydes as well as ketones.

Sodium Cyanoborohydride Uses

Salt cyanoborohydride is extensively made use of in the reduction of aldehydes as well as ketones, particularly the reductive amination of ketones. It is a decreasing representative for organic synthesis, reduction of aldehydes, ketones, oximes and also enamines, reduction of β-lactams to β-amino acids, as well as methylation of ammonia.

Although salt cyanoborohydride (NaBH3CN) is much less reducible than sodium borohydride, it is also steady in an acidic atmosphere of pH3. For that reason, it is typically made use of to decrease imine cations in acidic atmospheres. (Borch reductive amination).

Salt cyanoborohydride was utilized to manufacture novel phenate-bridged dilanthanum( III) facilities of rate of interest as versions for metalloproteins and also for their value in essential and also applied chemistry.

Salt cyanoborohydride is often made use of for reductive amination. Because the response rate of imide ion reduction is much faster than that of ketones and also aldehydes, reductive amination can be done as a one-pot process by introducing a decreasing representative into the mix of amine and also carbonyl compound.

  1. Contact with solid acids releases the highly poisonous gas HCN. A much safer minimizing representative that is fairly reactive is salt triacetoxyborohydride. Reduction with sodium cyanoborohydride:.
    In the visibility of sodium cyanoborohydride as well as tetrabutylammonium cyanoborohydride, the Xi-free Gies reaction of alkyl iodides with electron-deficient alkenes and the associated extreme carbonylation process proceeds efficiently. Transfer of iodine adhered to by hydride decrease of the resulting carbon-iodine bond is taken into consideration a feasible system.
  2. Borch as well as associates revealed that salt cyanoborohydride and lithium cyanoborohydride are acid-stable reagents with the ability of swiftly lowering carbonyl substances to alcohols at pH 3-4, likely through protonated carbonyl cations.
  3. Taking care to maintain a pH of 6-7, a blend of ketone or aldehyde catalysts, amine, as well as salt cyanide precisely provides the reductive amination item without competitive reduction of the carbonyl substratum. Although the Borch decrease problems are mild, salt cyanoborohydride and its spin-offs are highly harmful. Usage bromocresol green as a sign as well as maintain pH by adding HCl and/or KOH as required.

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Application of Sodium Cyanoborohydride

CN201310309028.9 provides a preparation method of a retigabine intermediate, comprising the following steps: p-fluorobenzaldehyde and 2-nitro-1,4-phenylenediamine are generated in an alcohol solvent under the action of a reducing agent After reaction, 2-amino-5-[(4-fluorobenzyl)amino]-1-nitrobenzene is obtained, and the reducing agent is sodium triacetoxyborohydride or sodium cyanoborohydride. The invention does not need to use toxic solvents and expensive catalysts, is economical and environmentally friendly, has low cost, and does not need complicated post-treatment. At the same time, the present invention uses sodium triacetoxyborohydride or sodium cyanoborohydride as a reducing agent, and the one-pot reaction is relatively complete, which greatly improves the yield of the target product. Experiments show that the yield of the preparation method provided by the present invention can reach more than 90%.

CN201310656241.7 reported a preparation method of a miglitol intermediate. The method uses tetrabenzyl glucose glycol as a raw material to obtain tetrabenzyl glucose dicarbonyl derivatives through Swern oxidation; this oxidation product is directly Double reductive amination with ethanolamine and sodium cyanoborohydride in the presence of a dehydrating agent can obtain tetrabenzyl miglitol, an important intermediate for the preparation of miglitol. The main advantage of this method is that the unstable tetrabenzyl glucose dicarbonyl derivative is directly used in the next step without separation, and in the double reductive amination reaction step, the 2-position R is directly obtained by selecting appropriate reaction conditions. The optically pure target product of the configuration saves the separation and purification step of the enantiomer mixture and the loss caused by the step, and the reaction time is short and the yield is high.

Preparation of Sodium Cyanoborohydride

  1. At a temperature of 0° C., accurately weigh 16 g of sodium borohydride (0.4 mol) and 300 ml of tetrahydrofuran into the reaction flask.
  2. The above mixture was slowly stirred for 30 min, and then 22 g (0.9 mol) of sodium hydride, 2.2 g of 15-crown-5, and 53 g (0.375 mol) of boron trifluoride ether solution were added.
  3. The mixture was refluxed and stirred for 8 hours, cooled to 20° C., the reaction was completed, filtered, and recrystallized with tetrahydrofuran to obtain 19.9 g of sodium cyanoborohydride with a yield of 91%.

Reference

  1. Sodium cyanoborohydride – PubChem
  2. [Chinese invention] CN201810649467.7 A kind of synthetic method of sodium cyanoborohydride

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