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Sodium triacetoxyborohydride

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(Redirected from 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))[1]
Melting point 116–120 °C (241–248 °F; 389–393 K)[1] decomposes
decomposition
Solubility 1,2-dichloroethane, dichloromethane, dioxane, methylene chloride, tetrahydrofuran, toluene,[2] benzene, dimethyl sulfoxide[3]
log P -2.88[4]
Structure
4 at boron atom
Tetrahedral at boron atom
Hazards
GHS labelling:[1]
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)
[4]
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)[1]
Related compounds
Other anions
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkYX markN ?)

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:[2]

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

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.[5][6][7]

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.[6]


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. [8]

Monoacetoxyborohydride

[edit]

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.[9]

References

[edit]
  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.
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