Date published: 2025-12-18

1-800-457-3801

SCBT Portrait Logo
Seach Input

Sodium triacetoxyborohydride (CAS 56553-60-7)

0.0(0)
Write a reviewAsk a question

Alternate Names:
Sodium tris(acetoxy)hydroborate; STAB
Application:
Sodium triacetoxyborohydride is a reagent used for reductive amination of carbonyl compounds with amines
CAS Number:
56553-60-7
Molecular Weight:
211.94
Molecular Formula:
C6H10BO6•Na
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

QUICK LINKS

Sodium triacetoxyborohydride is a reagent that has found use in organic chemistry, particularly in the field of reductive aminations, where it facilitates the conversion of aldehydes and ketones into amines. This compound is chosen for its selectivity and mild reaction conditions, which are for maintaining the integrity of sensitive substrates. Its stability and ease of handling make it a preferred choice for research involving complex molecule synthesis. In the study of catalysis, sodium triacetoxyborohydride plays a role in understanding the mechanisms of transfer hydrogenation, providing insights into efficient and selective catalytic processes. Researchers also employ this reagent in the synthesis of natural products and bioactive compounds, where the introduction of amine groups is a key step in the construction of molecular frameworks. The compound′s utility extends to materials science, where it is used to create nitrogen-doped materials with potential applications in electronics and energy storage.


Sodium triacetoxyborohydride (CAS 56553-60-7) References

  1. Synthesis and antimicrobial activity of squalamine analogue.  |  Kim, HS., et al. 2000. Bioorg Med Chem. 8: 2059-65. PMID: 11003150
  2. Total Syntheses of (-)-Papuamine and (-)-Haliclonadiamine.  |  McDermott, TS., et al. 1996. J Org Chem. 61: 700-709. PMID: 11666993
  3. Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1).  |  Abdel-Magid, AF., et al. 1996. J Org Chem. 61: 3849-3862. PMID: 11667239
  4. A Novel, One-Pot Reductive Alkylation of Amines by S-Ethyl Thioesters Mediated by Triethylsilane and Sodium Triacetoxyborohydride in the Presence of Palladium on Carbon.  |  Han, Y. and Chorev, M. 1999. J Org Chem. 64: 1972-1978. PMID: 11674291
  5. Solution-phase library synthesis of furanoses.  |  Krueger, EB., et al. 2002. J Comb Chem. 4: 229-38. PMID: 12005483
  6. Total synthesis of (-)-himgaline.  |  Shah, U., et al. 2006. J Am Chem Soc. 128: 12654-5. PMID: 17002352
  7. Synthesis of a histamine H(3) receptor antagonist-manipulation of hydroxyproline stereochemistry, desymmetrization of homopiperazine, and nonextractive sodium triacetoxyborohydride reaction workup.  |  Pippel, DJ., et al. 2010. J Org Chem. 75: 4463-71. PMID: 20536151
  8. A One-Pot Selective Synthesis of N-Boc Protected Secondary Amines: Tandem Direct Reductive Amination/N-Boc Protection.  |  Neelarapu, R. and Petukhov, PA. 2012. Tetrahedron. 68: 7056-7062. PMID: 22844160
  9. mt-tRNA components: synthesis of (2-thio)uridines modified with blocked glycine/taurine moieties at C-5,1.  |  Leszczynska, G., et al. 2013. Nucleosides Nucleotides Nucleic Acids. 32: 599-616. PMID: 24138499
  10. Synthesis and Structure-Activity Relationships of Novel Benzylamine-Type Antifungals as Butenafine-Related Antimycotics.  |  Krauss, J., et al. 2017. Arch Pharm (Weinheim). 350: PMID: 28376264
  11. N-Alkylation Using Sodium Triacetoxyborohydride with Carboxylic Acids as Alkyl Sources.  |  Tamura, S., et al. 2018. Chem Pharm Bull (Tokyo). 66: 101-103. PMID: 29311505
  12. Synthesis of Aza-acyclic Nucleoside Libraries of Purine, Pyrimidine, and 1,2,4-Triazole.  |  Pathak, V., et al. 2019. ACS Comb Sci. 21: 183-191. PMID: 30653914
  13. Quantitative GC determination of sodium triacetoxyborohydride (STAB).  |  Hale, I., et al. 2021. J Pharm Biomed Anal. 203: 114213. PMID: 34252843
  14. Density Functional Theory Study on the Selective Reductive Amination of Aldehydes and Ketones over Their Reductions to Alcohols Using Sodium Triacetoxyborohydride.  |  Oliphant, SJ. and Morris, RH. 2022. ACS Omega. 7: 30554-30564. PMID: 36061668

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Sodium triacetoxyborohydride, 25 g

sc-253600
25 g
$42.00