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]
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Other names
NaBH(OAc)3; STAB; STABH; Sodium triacetoxyhydroborate
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Identifiers | |
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3D model (JSmol)
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ECHA InfoCard | 100.115.747 |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
Na[(CH3COO)3BH] | |
Molar mass | 211.94 g·mol−1 |
Appearance | White powder |
Density | 1.20 g/cm3 |
Melting point | 116 to 120 °C (241 to 248 °F; 389 to 393 K) decomposes |
decomposition | |
Structure | |
4 at boron atom | |
Tetrahedral at boron atom | |
Hazards | |
NFPA 704 (fire diamond) | |
Safety data sheet (SDS) | External MSDS |
Related compounds | |
Other anions
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Sodium cyanoborohydride |
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
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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.[2][3][4]
However, unlike sodium cyanoborohydride, the triacetoxyborohydride hydrolyzes readily, 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. [5]
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.[6]
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