Sodium triacetoxyborohydride

Sodium triacetoxyborohydride
Sodium_triacetoxyborohydride
Sodium_triacetoxyborohydride
Names
IUPAC name
Sodium tris(acetato-kappaO)(hydrido)borate(1-)
Other names
  • Borate(1-), tris(acetato-kappaO)hydro-, sodium (1:1), (T-4)-
  • STAB
  • STABH
  • Sodium triacetoxyhydroborate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.115.747 Edit this at Wikidata
EC Number
  • 611-401-0
UNII
UN number 1409
  • InChI=1S/C6H9BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h1-3H3;/q-1;+1
    Key: AGGHKNBCHLWKHY-UHFFFAOYSA-N
  • [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]
Properties
Na[(CH3COO)3BH]
Molar mass 211.94 g·mol−1
Appearance White powder
Density 1.36 g/cm3 (20.1 °C (68.2 °F; 293.2 K))
Melting point 116–120 °C (241–248 °F; 389–393 K) decomposes
decomposition
Solubility 1,2-dichloroethane, dichloromethane, dioxane, methylene chloride, tetrahydrofuran, toluene, benzene, dimethyl sulfoxide
log P -2.88
Structure
4 at boron atom
Tetrahedral at boron atom
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
H228, H260, H302, H318, H360FD
P201, P202, P210, P223, P231+P232, P240, P241, P264, P270, P280, P301+P312+P330, P305+P351+P338+P310, P308+P313, P335+P334, P370+P378, P402+P404, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 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 hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
2
2
2
W
360 °C (680 °F; 633 K)
Related compounds
Other anions
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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, sodium triacetoxyborohydride quickly decomposes upon contact with methanol. It reacts only slowly with ethanol and isopropanol and therefore can be used with these solvents.


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.

References

  1. 1 2 3 4 Sigma-Aldrich Co., Sodium triacetoxyborohydride. Retrieved on 13 March 2026.
  2. 1 2 Gribble, Gordon W.; Abdel-Magid, Ahmed F. (15 March 2007). "Sodium Triacetoxyborohydride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rs112.pub2.
  3. ↑ "Sodium triacetoxyborohydride, 95% (Product Page)". www.fishersci.com. ThermoFisher Scientific. Retrieved 13 March 2026.
  4. 1 2 "SDS - Sodium triacetoxyborohydride" (pdf). www.fishersci.com. 5. ThermoFisher Scientific. 21 December 2025 [16 January 2015]. p. 3. Retrieved 13 March 2026.
  5. ↑ 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 Procedures". The Journal of Organic Chemistry. 61 (11): 3849–3862. doi:10.1021/jo960057x. PMID 11667239.
  6. 1 2 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.
  7. ↑ 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.
  8. ↑ Pandit, C.R.; Mani, N.S. (2009). "Expedient reductive amination of aldehyde bisulfite adducts". Synthesis (23): 4032–4036. doi:10.1055/s-0029-1217050.
  9. ↑ 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.