Sodium triacetoxyborohydride

Sodium triacetoxyborohydride
Sodium_triacetoxyborohydride
Names
Other names
NaBH(OAc)3; STAB; STABH; Sodium triacetoxyhydroborate
Identifiers
3D model (JSmol)
ECHA InfoCard 100.115.747 Edit this at Wikidata
UNII
  • InChI=1S/C6H9BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h1-3H3;/q-1;+1
    Key: AGGHKNBCHLWKHY-UHFFFAOYSA-N
  • [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
4
2
Safety data sheet (SDS) External MSDS
Related compounds
Other anions
 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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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]

Na[BH4] + 3 CH3COOH → Na[(CH3COO)3BH] + 3 H2
  1. ^ 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