Sodium triacetoxyborohydride
| Names | |
|---|---|
| IUPAC name
Sodium triacetoxyborohydride
| |
| Other names
NaBH(OAc)3
STAB STABH | |
| Properties | |
| C6H10BNaO6 Na(CH3COO)3BH | |
| Molar mass | 211.94 g/mol |
| Appearance | White solid |
| Odor | Odorless |
| Density | 1.20 g/cm3 |
| Melting point | 116–120 °C (241–248 °F; 389–393 K) (decomposition) |
| Boiling point | Decomposes |
| Reacts | |
| Solubility | Soluble in DMF Slightly soluble in THF Insoluble in chloroform |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
500 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
Sodium borohydride Sodium cyanoborohydride |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| 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.
Contents
Properties
Chemical
Sodium triacetoxyborohydride is a milder reducing agent than sodium borohydride or even sodium cyanoborohydride. It can reduce aldehydes but does not reduce most ketones. It is especially suitable for reductive aminations of aldehydes and ketones.
However, unlike sodium cyanoborohydride, the triacetoxyborohydride hydrolyzes readily in water, and also reacts with methanol. It also reacts with ethanol and isopropanol, albeit much slower.
STABH may also be used for reductive alkylation of secondary amines with aldehyde-bisulfite adducts.
Physical
Sodium triacetoxyborohydride is a white hygroscopic solid.
Availability
STAB is sold by chemical suppliers.
Preparation
Sodium triacetoxyborohydride can be prepared by protonolysis of sodium borohydride with acetic acid:[1]
- NaBH4 + 3 HO2CCH3 → NaBH(O2CCH3)3 + 3 H2
Projects
- Reducing agent
Handling
Safety
Sodium triacetoxyborohydride hydrolyzes in water to release hydrogen, which is flammable.
Storage
Should be kept in airtight bottles, or in a desiccator.
Disposal
Can be neutralized by careful hydrolysis.
References
- ↑ Gordon W. Gribble, Ahmed F. Abdel-Magid, "Sodium Triacetoxyborohydride" Encyclopedia of Reagents for Organic Synthesis, 2007, John Wiley & Sons.
