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Sodium triacetoxyborohydride

Name: Sodium triacetoxyborohydride
Brand: ALDRICH

>95%

Synonym(s):

STAB

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About This Item

Linear Formula:

(CH₃COO)₃BHNa

CAS Number:

56553-60-7

Molecular Weight:

211.94

UNSPSC Code:

12352302

NACRES:

NA.22

PubChem Substance ID:

24859012

MDL number:

MFCD00012211

Beilstein/REAXYS Number:

4047608

Assay:

>95%

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Properties

Quality Level

200

assay

>95%

reaction suitability

reagent type: reductant

greener alternative product score

old score: 5
new score: 1
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greener alternative product characteristics

Waste Prevention
Design for Energy Efficiency
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

116-120 °C (dec.) (lit.)

greener alternative category

Re-engineered

SMILES string

[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

Description

General description

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

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives. This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Design for Energy Efficiency” and “Use of Renewable Feedstocks”. Click here to view its DOZN scorecard.

Application

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.

Applications using Sodium triacetoxyborohydride