Sodium triacetoxyborohydride
| Sodium_triacetoxyborohydride | |
| Names | |
|---|---|
| Other names
NaBH(OAc)3; STAB; STABH; Sodium triacetoxyhydroborate
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| Identifiers | |
| 56553-60-7 | |
| PubChem | 23676153 |
| Properties | |
| C6H10BNaO6 | |
| Molar mass | 211.96 g/mol |
| Appearance | white powder |
| Density | 1.20 g/cm3 |
| Melting point | 116 to 120 °C (241 to 248 °F; 389 to 393 K) decomposes |
| decomposition | |
| Vapor pressure | {{{value}}} |
| Related compounds | |
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Other anions
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Sodium cyanoborohydride |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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:[1]
- 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.[2][3]
However, unlike sodium cyanoborohydride, the triacetoxyborohydride is water-sensitive, and water cannot be used as a solvent with this reagent, nor is it compatible with methanol. It reacts only slowly with ethanol and isopropanol and can be used with these.[3]
NaBH(OAc)3 may also be used for reductive alkylation of secondary amines with aldehyde-bisulfite adducts. [4]
References
- ↑ 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
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