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316393

Sigma-Aldrich

Sodium triacetoxyborohydride

97%

Synonym(s):

STAB

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About This Item

Linear Formula:
(CH3COO)3BHNa
CAS Number:
56553-60-7
Molecular Weight:
211.94
Beilstein:
4047608
MDL number:
MFCD00012211
UNSPSC Code:
12352302
PubChem Substance ID:
24859012
NACRES:
NA.22

Quality Level

200

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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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

EUH014

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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Certificates of Analysis (COA)

Lot/Batch Number
0000304347
STBL4792
STBL3642
0000264876
0000215798

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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)
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
Synlett, 537-537 (1990)
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)
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Sodium Triacetoxyborohydride

Sodium triacetoxyborohydride

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