NaBH(OAc)3; STAB; STABH; Sodium triacetoxyhydroborate
|Molar mass||211.96 g/mol|
|Melting point||116 to 120 °C (241 to 248 °F; 389 to 393 K) decomposes|
|EU Index||not listed|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
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:
- NaBH4 + 3 HO2CCH3 → NaBH(O2CCH3)3 + 3 H2
Owing to the steric and electronic effects of the acetoxy groups, sodium triacetoxyborohydride is a milder reducing agent than sodium borohydride or even sodium cyanoborohydride. Furthermore, NaBH(OAc)3 avoids the toxic side-products generated by sodium cyanoborohydride. Sodium triacetoxyborohydride is especially suitable for reductive aminations of aldehydes and ketones.
However, unlike sodium cyanoborohydride, the triacetoxyborohydride is water-sensitive and water cannot be used as a solvent with this reagent, neither is it compatible with methanol. It reacts only slowly with ethanol and isopropanol and can be used with these.
NaBH(OAc)3 may also be used for reductive alkylation of secondary amines with aldehyde-bisulfite adducts. 
- 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
- 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.
- 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.
- Pandit, C. R.; Mani, N. S. (2009). "Expedient reductive amination of aldehyde bisulfite adducts.". Synthesis (23): 4032–4036.
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