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Sigma-Aldrich

Sodium triacetoxyborohydride

97%

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Synonym(s):
STAB
Linear Formula:
(CH3COO)3BHNa
CAS Number:
Molecular Weight:
211.94
Beilstein:
4047608
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

reaction suitability

reagent type: reductant

mp

116-120 °C (dec.) (lit.)

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

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1 of 4

This Item
SAB1406490Z699365HPA061642
Swabs and SwabChecks Buffer Swabs, capacity 4 mL

Z699365

Swabs and SwabChecks

reaction suitability

reagent type: reductant

reaction suitability

-

reaction suitability

-

reaction suitability

-

mp

116-120 °C (dec.) (lit.)

mp

-

mp

-

mp

-

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.

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

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Product No.
Description
Pricing

Signal Word

Danger

Hazard Classifications

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

Supplementary Hazards

Storage Class Code

4.3 - Hazardous materials, which set free flammable gases upon contact with water

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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)
Use of Sodium Triacetoxyborohydride in Reductive Amination of Ketones and Aldehydes
Abdel-Magid et al.
ACS Symp. Ser., 641, 201-216 (1996)
Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride
Abdel-Magid AF, Maryanoff CA, Carson KG
Tetrahedron Letters, 31 (39), 5595-5598 (1990)
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)
Easy access to N-alkylation of N-unsubstituted [60]fulleropyrrolidines: reductive amination using sodium triacetoxyborohydride
Tetrahedron Letters, 45, 3975-3978 (2004)

Articles

Sodium triacetoxyborohydride

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