Chemistry:Sodium triacetoxyborohydride
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| Names | |
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| IUPAC name
Sodium tris(acetato-kappaO)(hydrido)borate(1-)
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
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PubChem CID
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| UNII | |
| UN number | 1409 |
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| Properties | |
| Na[(CH 3COO) 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 pictograms |    
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| GHS Signal word | Danger |
| H228, H260, H302, H318, H360FD | |
| P201, P202, P210, P223, P231+232, P240, P241, P264, P270, P280, P301+312+330Script error: No such module "Preview warning".Category:GHS errors, P305+351+338+310, P308+313, P335+334, P370+378, P402+404, P405, P501 | |
| NFPA 704 (fire diamond) | |
| 360 °C (680 °F; 633 K)[1] | |
| Related compounds | |
Other anions
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na[(CH
3COO)
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[BH
4] + 3 CH
3COOH → Na[(CH
3COO)
3BH] + 3 H
2
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.[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]
NaBH(OAc)
3 may also be used for reductive alkylation of secondary amines with aldehyde-bisulfite adducts. [8]
Monoacetoxyborohydride
The combination of Na[BH
4] 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
- ↑ 1.0 1.1 1.2 1.3 Sigma-Aldrich Co., Sodium triacetoxyborohydride. Retrieved on 13 March 2026.
- ↑ 2.0 2.1 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.
- ↑ "Sodium triacetoxyborohydride, 95% (Product Page)" (in en). ThermoFisher Scientific. https://www.fishersci.com/shop/products/sodium-triacetoxyborohydride-95-thermo-scientific/AAB2206006.
- ↑ 4.0 4.1 "SDS - Sodium triacetoxyborohydride" (pdf). ThermoFisher Scientific. 21 December 2025. p. 3. https://www.fishersci.com/store/msds?partNumber=AAB2206006&productDescription=SOD+TRIACETOXYBOROHYDRID+95+5G&vendorId=VN00024248&countryCode=US&language=en.
- ↑ 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.
- ↑ 6.0 6.1 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.
- ↑ 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.
- ↑ Pandit, C.R.; Mani, N.S. (2009). "Expedient reductive amination of aldehyde bisulfite adducts.". Synthesis (23): 4032–4036. doi:10.1055/s-0029-1217050.
- ↑ Gribble, Gordon W. (1998). "Sodium borohydride in carboxylic acid media: a phenomenal reduction system". Chemical Society Reviews 27 (6): 395. doi:10.1039/A827395Z.
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