Sodium triacetoxyborohydride

Sodium triacetoxyborohydride 속성

Sodium triacetoxyborohydride MSDS

STAB

Sodium triacetoxyborohydride C화학적 특성, 용도, 생산

화학적 성질

Sodium triacetoxyborohydride (STAB-H) is commercially available as a hygroscopic white powder with a melting point of 116-120 °C. freely soluble in benzene. It is prepared by the reaction of NaBH4 with excess acetic acid in benzene or toluene.

용도

Sodium Triacetoxyborohydride(STAB) is a hydride reagent used in stereoselective reductive amination. It is able to replace toxic sodium cyanoborohydride under most conditions. It is selective in reducing aldehydes to alcohols in the presence of ketones. STAB is also stable in anhydrous acids, which enables reductive amination of aldehydes and ketones. It used in reductive amination of ketones and aldehydes and reductive amination/lactamization of carbonyl compounds with amines. The advantage of STAB compared to sodium cyanoborohydride is evident. STAB, being non-toxic, is easier to handle and forms no toxic by-products, making the treatment of process waste after the reaction simple and less costly.

주요 응용

Sodium triacetoxyborohydride is a mild reagent that exhibits remarkable selectivity as a reducing agent. It reduces aldehydes but not ketones; however, beta-hydroxyketones can be reduced selectively to give 1,3-trans diols.The steric and the electron-withdrawing effects of the three acetoxy groups stabilize the boron-hydrogen bond and are responsible for its mild reducing properties.
Sodium triacetoxyborohydride or [NaBH(OAc)3] can be used as a reagent:
In the reductive amination of ketones and aldehydes.
To prepare N-benzyl-γ-valerolactam by reacting with methyl 4-oxopentanoate and benzylamine via reductive amination/lactamization.
To reduce imines and enamines to corresponding amines.
To reduce quinolines and isoquinolines to corresponding tetrahydro derivatives.
In the hydroboration of alkenes.
To synthesize nitroxide biradicals for creating high relaxivity terminal groups linkage to dendrimers.

화학 반응

Sodium Triacetoxyborohydride is selective reducing agent in organic synthesis. It is especially suitable for reductive aminations. Since the reaction rate for the reduction of iminium ions is much faster than for ketones or even aldehydes, the reductive amination can be carried out as a one-pot procedure by introducing the reducing agent into a mixture of the amine and carbonyl compound. The presence of a stoichiometric amount of acetic acid, which catalyzes the imine formation and provides the iminium ion, doesn't present any problem under these conditions.

Reductive amination (simplified)

Sodium triacetoxyborohydride 준비 용품 및 원자재

원자재

준비 용품

Sodium triacetoxyborohydride 공급 업체

공급자	전화	이메일	국가	제품 수	이점
Hebei Guanlang Biotechnology Co,.LTD	+8619930503252	daisy@crovellbio.com	China	5964	58
Shandong Believe Chemical PTE.LTD	+86-18553607090 +8618553607090	1093908296@qq.com	China	1684	58
Wuhan wingroup Pharmaceutical Co., Ltd	+86-13296627870; +8613296627870	info@whwingroup.com	China	703	58
Wuhan Mayue Longteng Technology Development Co., Ltd.	+undefined15171477138	helen.yan@lantu-tech.com	China	287	58
Hebei Mojin Biotechnology Co., Ltd	+8613288715578	sales@hbmojin.com	China	12456	58
Shanghai UCHEM Inc.	+862156762820 +86-13564624040	sales@myuchem.com	China	6710	58
Dorne Chemical Technology co. LTD	+86-13583358881 +86-18560316533	Ethan@dornechem.com	China	294	58
Shaanxi Haibo Biotechnology Co., Ltd	+undefined18602966907	qinhe02@xaltbio.com	China	1000	58
Anhui Ruihan Technology Co., Ltd	+8617756083858	daisy@anhuiruihan.com	China	994	58
Wuhan Ruichi Technology Co., Ltd	+8613545065237	admin@whrchem.com	China	164	58

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