Sodium triacetoxyborohydride
CAS:56553-60-7
MF:C6H10BNaO6
Sodium Triacetoxyborohydride(STAB) is a hydride reagent used in stereoselective reductive amination. It is able to replace toxic sodium cyanoborohydride under most conditions. It is selective in reducing aldehydes to alcohols in the presence of ketones.
- Description
- Additional information
Description
Sodium triacetoxyborohydride CAS 56553-60-7 Product Information
| Product Name: | Sodium Triacetoxyborohydride (Technical Grade) |
| Synonyms: | SODIUM TRIACETOXYBOROHYDRIDE;sodiumtriacetoxyborohydride,calselect?stab;Sodium triacetohydroborate, Triacetohydroborate sodium salt;Sodiumtriacetoxyborohydride,95%;Sodium tris(acetoxy)borohydride, Tris(acetoxy)hydroborate sodium salt;Sodium tris(acetoxy)hydroborate 97%;Sodium Triacetoxyborohydride (Technical Grade);SodiuM triacetoxyborohydride 97% |
| CAS NO: | 56553-60-7 |
| Molecular Weight: | 211.94 |
| Molecular Formula: | C6H10BNaO6 |
| Boiling Point: | 111.1℃[at 101 325 Pa] |
| Melting point: | 116-120 °C (dec.) (lit.) |
| Density: | 1.36[at 20℃] |
| Appearance: | White to Off-White Solid |
| Applications: | Sodium triacetoxyborohydride is a mild reagent that exhibits remarkable selectivity as a reducing agent. It reduces aldehydes but not ketones. |
| Solubility: | Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride. |
| Storage: | Inert atmosphere, Room Temperature |
sodium cyanoborohydride vs sodium triacetoxyborohydride
TriAcetOxyBorohydride is a safer reducing agent than Sodium cyanoborohydride with comparable reactivity . The boron-hydrogen bond is stabilized by the steric and electron-withdrawing effects of the acetoxy groups, making sodium triacetoxyborohydride a mild reducing agent.
sodium triacetoxyborohydride synthesis
Sodium triacetoxyborohydride can be prepared by protonolysis of sodium borohydride with acetic acid: NaBH4 + 3 HO2CCH3 → NaBH(O2CCH3)3 + 3 H.
sodium triacetoxyborohydride safety/sodium triacetoxyborohydride hazards
Avoid contact with skin, eyes or clothing. Avoid ingestion and inhalation. Keep away from open flames, hot surfaces and sources of ignition. Handle under inert gas, protect from moisture.
sodium triacetoxyborohydride reductive amination
Sodium triacetoxyborohydride is presented as a general reducing agent for the reductive amination of aldehydes and ketones. Procedures for using this mild and selective reagent have been developed for a wide variety of substrates.
sodium triacetoxyborohydride solubility/sodium triacetoxyborohydride solubility in organic solvents
Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride.
sodium triacetoxyborohydride mechanism/reductive amination mechanism sodium triacetoxyborohydride
The boron-hydrogen bond is stabilized by the steric and electron-withdrawing effects of the acetoxy groups, making sodium triacetoxyborohydride a mild reducing agent. Sodium triacetoxyborohydride is especially suitable for reductive aminations.
sodium triacetoxyborohydride reaction with water
Sodium triacetoxyborohydride hydrolyzes in water to release hydrogen, which is flammable.
sodium triacetoxyborohydride decomposition
n case of an uptake via oral, inhalation or dermal route, Sodium triacetoxyborohydride comes into contact with wet mucosa in the mouth, respiratory tract or sweat on the skin, and consequently decomposes to final products hydrogen and boric acid.
Additional information
| Melting Point | 116-120 °C (dec.) (lit.) |
|---|---|
| Solubility | Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride. |
| Color | White |
| Form | Powder |
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