Skip to Content

Key Documents

View All Documentation

316393

Sodium triacetoxyborohydride

>95%

greener alternative

Greener Alternative

Synonym(s):

STAB

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

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%
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Segment

200

assay

>95%

reaction suitability

reagent type: reductant

greener alternative product score

old score: 5
new score: 1
Find out more about DOZN™ Scoring

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

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

Still not finding the right product?

Explore all of our products under Sodium triacetoxyborohydride

signalword

Danger

supp_hazards

EUH014

Storage Class

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

Hazard Classifications

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library