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Sodium triacetoxyborohydride

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Sodium triacetoxyborohydride
Sodium_triacetoxyborohydride
Sodium_triacetoxyborohydride
Names
Other names NaBH(OAc)3; STAB; STABH; Sodium triacetoxyhydroborate
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.115.747 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H9BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h1-3H3;/q-1;+1Key: AGGHKNBCHLWKHY-UHFFFAOYSA-N
SMILES
  • (OC(=O)C)(OC(=O)C)OC(=O)C.
Properties
Chemical formula Na[(CH3COO)3BH]
Molar mass 211.94 g·mol
Appearance White powder
Density 1.20 g/cm
Melting point 116 to 120 °C (241 to 248 °F; 389 to 393 K) decomposes
Solubility in water decomposition
Structure
Coordination geometry 4 at boron atom
Molecular shape Tetrahedral at boron atom
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3 4 2
Safety data sheet (SDS) External MSDS
Related compounds
Other anions Sodium cyanoborohydride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na[(CH3COO)3BH]. Like other borohydrides, it is used as a reducing agent in organic synthesis. This colourless salt is prepared by protonolysis of sodium borohydride with acetic acid:

Na[BH4] + 3 CH3COOH → Na[(CH3COO)3BH] + 3 H2

Comparison with related reagents

Sodium triacetoxyborohydride is a milder reducing agent than sodium borohydride or even sodium cyanoborohydride. It reduces aldehydes but not most ketones. It is especially suitable for reductive aminations of aldehydes and ketones.

However, unlike sodium cyanoborohydride, the triacetoxyborohydride hydrolyzes readily, nor is it compatible with methanol. It reacts only slowly with ethanol and isopropanol and can be used with these.


Reductive amination with STAB
Reductive amination with STAB

NaBH(OAc)3 may also be used for reductive alkylation of secondary amines with aldehyde-bisulfite adducts.

Monoacetoxyborohydride

The combination of Na[BH4] with carboxylic acids results in the formation of acyloxyborohydride species other than sodium triacetoxyborohydride. These modified species can perform a variety of reductions not normally associated with borohydride chemistry, such as alcohols to hydrocarbons and nitriles to primary amines.

See also

References

  1. Gordon W. Gribble, Ahmed F. Abdel-Magid, "Sodium Triacetoxyborohydride" Encyclopedia of Reagents for Organic Synthesis, 2007, John Wiley & Sons.doi:10.1002/047084289X.rs112.pub2
  2. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. (1996). "Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures1". The Journal of Organic Chemistry. 61 (11): 3849–3862. doi:10.1021/jo960057x. PMID 11667239.
  3. ^ Abdel-Magid, A. F.; Mehrman, S. J. (2006). "A Review on the Use of Sodium Triacetoxyborohydride in the Reductive Amination of Ketones and Aldehydes". Organic Process Research & Development. 10 (5): 971. doi:10.1021/op0601013.
  4. Magano, Javier; Kiser, E. Jason; Shine, Russell J.; Chen, Michael H. (2013). "Oxindole Synthesis via Palladium-catalyzed C-H Functionalization". Organic Syntheses. 90: 74. doi:10.15227/orgsyn.090.0074.
  5. Pandit, C. R.; Mani, N. S. (2009). "Expedient reductive amination of aldehyde bisulfite adducts". Synthesis (23): 4032–4036.
  6. Gribble, Gordon, W. (1998). "Sodium borohydride in carboxylic acid media: a phenomenal reduction system". Chemical Society Reviews. 27 (6): 395. doi:10.1039/A827395Z. S2CID 96906861.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. Houri, Ahmad F.; Hoveyda, Amir H. (2001). "Tetramethylammonium Triacetoxyborohydride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt059. ISBN 0-471-93623-5.
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