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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

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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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Use of Sodium Triacetoxyborohydride in Reductive Amination of Ketones and Aldehydes
Abdel-Magid et al.
ACS Symp. Ser., 641, 201-216 (1996)
Easy access to N-alkylation of N-unsubstituted [60]fulleropyrrolidines: reductive amination using sodium triacetoxyborohydride
Tetrahedron Letters, 45, 3975-3978 (2004)
Sodium Triacetoxyborohydride
Gribble GW and Abdel-Magid AF
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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