316393

Sigma-Aldrich

Sodium triacetoxyborohydride

97%

Synonym(s):
STAB
Linear Formula:
(CH3COO)3BHNa
CAS Number:
Molecular Weight:
211.94
Beilstein/REAXYS Number:
4047608
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

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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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.

Packaging

25, 100, 500 g in poly bottle
1, 25 kg in steel drum

Signal Word

Danger

Supp Hazards

EUH014

RIDADR

UN 1409 4.3 / PGII

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is Product 316393, Sodium triacetoxyborohydride, used for?

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

  4. Which is better to use, Product 316393, Sodium triacetoxyborohydride, or sodium cyanoborohydride?

    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. (See Chemfiles, vol 5, no. 9).   The reductive aminations of complex substrates also proceed smoothly using sodium triacetoxyborohydride.

  5. How else can Product 316393, Sodium triacetoxyborohydride, be used as a reducing agent?

    Recently, sodium triacetoxyborohydride was used to stereoselectively reduce    4-ketoprolines to the corresponding trans-hydroxy-proline in excellent yields.  By comparison, reduction of the 4-ketoproline esters failed to provide any product.

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

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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)
ACS Symp. Ser., 641, 201-216 (1996)
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)
Tetrahedron Letters, 45, 3975-3978 (2004)
Sodium Triacetoxyborohydride
Gribble GW and Abdel-Magid AF
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Articles
Sodium triacetoxyborohydride
Read More

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