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
CAS Number	56553-60-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	2007055;
ECHA InfoCard	100.115.747
EC Number	611-401-0;
PubChem CID	23676153;
UNII	4VU0JE4YSK ;
UN number	1409
CompTox Dashboard (EPA)	DTXSID8074368 ;
	InChI 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;
	SMILES [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+];
Properties
Chemical formula	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
Solubility in water	decomposition
Solubility	1,2-dichloroethane, dichloromethane, dioxane, methylene chloride, tetrahydrofuran, toluene, benzene, dimethyl sulfoxide
log P	-2.88
Structure
Coordination geometry	4 at boron atom
Molecular shape	Tetrahedral at boron atom
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H228, H260, H302, H318, H360FD
Precautionary statements	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)	2 2 2 W
Autoignition; temperature	360 °C (680 °F; 633 K)
Related compounds
Other anions	Sodium borohydride; Sodium cyanoborohydride;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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

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[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

^ ^a ^b ^c ^d Sigma-Aldrich Co., Sodium triacetoxyborohydride. Retrieved on 13 March 2026.
^ ^a ^b 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)". www.fishersci.com. ThermoFisher Scientific. Retrieved 13 March 2026.
^ ^a ^b "SDS - Sodium triacetoxyborohydride" (pdf). www.fishersci.com. 5. ThermoFisher Scientific. 21 December 2025 [16 January 2015]. p. 3. Retrieved 13 March 2026.
^ 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.
^ ^a ^b 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. S2CID 96906861.

[SigmaAldrich-1] Sigma-Aldrich Co., Sodium triacetoxyborohydride. Retrieved on 13 March 2026.

[Gribble2007-2] 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.

[FisherSDS-4] "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.

[oprd-6] 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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