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316393

Sigma-Aldrich

三乙酰氧基硼氢化钠

97%

别名:

STAB

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About This Item

线性分子式:
(CH3COO)3BHNa
CAS号:
56553-60-7
分子量:
211.94
Beilstein:
4047608
MDL编号:
MFCD00012211
UNSPSC代码:
12352302
PubChem化学物质编号:
24859012
NACRES:
NA.22

质量水平

200

检测方案

97%

反应适用性

reagent type: reductant

mp

116-120 °C (dec.) (lit.)

SMILES字符串

[Na+].CC(=O)O[BH-](OC(C)=O)OC(C)=O

InChI

1S/C6H10BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h7H,1-3H3;/q-1;+1

InChI key

HHYFEYBWNZJVFQ-UHFFFAOYSA-N

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相关类别

一般描述

由于其大范围、温和性和选择性，三乙酰氧基硼氢化钠（NaBH(OAc)3）是一种特别有效的还原胺化试剂。 由于合成中形成的副产物毒性较低、产率更高和可再现性，它在很多应用中都优于氰基硼氢化钠。

应用

三乙酰氧基硼氢化钠[NaBH(OAc)3]可用作以下用途试剂：
  • 酮和醛的还原胺化。
  • 与4-氧代戊酸甲酯和苄胺反应，通过还原胺化/内酰胺化制备N-苄基-γ-戊内酰胺。
  • 将亚胺和烯胺还原成相应的胺。
  • 将喹啉和异喹啉还原为相应的四氢衍生物。
  • 烯烃的硼氢化。
  • 合成氮氧双自由基，形成与树枝状大分子连接的高弛豫性末端基团。
使用三乙酰氧基硼氢化钠的应用

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说明
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警示用语：

Danger

危险分类

Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Sol. 1 - Repr. 1B - Water-react 1

补充剂危害

EUH014

WGK

WGK 2

闪点(°F)

Not applicable

闪点(°C)

Not applicable

分析证书(COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is Product 316393, Sodium triacetoxyborohydride, used for?

    Sodium triacetoxyborohydride (NaBH(OAc)3) is particularly effective in reductive aminations due to its large scope, mildness, and selectivity.

  4. Which is better to use, Product 316393, Sodium triacetoxyborohydride, or sodium cyanoborohydride?

    It is preferred to sodium cyanoborohydride (NaBH3CN) in many applications due to reduced toxicity of the side products formed, and better yields and reproducibility during synthesis. (See Chemfiles, vol 5, no. 9).   The reductive aminations of complex substrates also proceed smoothly using sodium triacetoxyborohydride.

  5. How else can Product 316393, Sodium triacetoxyborohydride, be used as a reducing agent?

    Recently, sodium triacetoxyborohydride was used to stereoselectively reduce    4-ketoprolines to the corresponding trans-hydroxy-proline in excellent yields.  By comparison, reduction of the 4-ketoproline esters failed to provide any product.

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Synlett, 537-537 (1990)
Ethan M McBride et al.
Forensic science international, 288, 278-282 (2018-05-23)
Impurity profiling has been used as a useful tool for analyzing nearly every drug class currently known on the illicit market. Impurities present within seized samples have the potential to determine source of origin, route of synthesis used, as well
Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1)
Abdel-Magid AF, Carson KG, Harris BD, Maryanoff CA, Shah RD.
The Journal of Organic Chemistry, 61(11), 3849-3862 (1996)
Methods of enhancement of reactivity and selectivity of sodium borohydride for applications in organic synthesis
Periasamy M and Thirumalaikumar M
Journal of Organometallic Chemistry, 609(1-2), 137-151 (2000)
A review on the use of sodium triacetoxyborohydride in the reductive amination of ketones and aldehydes
Abdel-Magid AF and Mehrman SJ
Organic Process Research & Development, 10(5), 971-1031 (2006)
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