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316393 Sigma-Aldrich

Sodium triacetoxyborohydride

97%

Synonym: STAB

  • CAS Number 56553-60-7

  • Linear Formula (CH3COO)3BHNa

  • Molecular Weight 211.94

  •  Beilstein Registry Number 4047608

  •  MDL number MFCD00012211

  •  PubChem Substance ID 24859012

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Properties

Related Categories Borohydrides, Chemical Synthesis, Reduction, Synthetic Reagents
InChI Key   HHYFEYBWNZJVFQ-UHFFFAOYSA-N
assay   97%
mp   116-120 °C (dec.) (lit.)

Description

Packaging

1, 10, 25 kg in steel drum

25, 100, 500 g in poly bottle

Application

Reagent used in reductive amination of ketones and aldehydes and reductive amination/lactamization of carbonyl compounds with amines.
Reagent for the reductive amination of aryl aldehydes.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Supplemental Hazard Statements 
Reacts violently with water.
RIDADR 
UN 1409 4.3 / PGII
WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Frequently Asked Questions

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.
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.
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.
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.
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.
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 orview local office numbers.
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.
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Protocols & Articles

Articles

Sodium triacetoxyborohydride

Amine synthesis is one of the most common organic transformations when designing new drug candidates, and the reductive amination of carbonyl compounds is among the most useful and important tools to...
ChemFiles Volume 5 Article 9
Keywords: Aminations, Applications, Cyclizations, Metathesis, Reductions, Reductive aminations, Ring-closing metathesis, Tools

Peer-Reviewed Papers
15

References

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