What is Sodium Triacetoxyborohydride CAS 56553-60-7?

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. It is a white powder with a density of 1.20 g/cm3 and a melting point of 116 to 120 °C (241 to 248 °F; 389 to 393 K). 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. 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. Sodium triacetoxyborohydride 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

Sodium Triacetoxyborohydride CAS 56553-60-7 Product Parameter

Synonyms

stab; Sodium triacetoborohydride; Sodium Triacetoxyborohyride; SODIUM TRIACETOXYHYDROBORATE; sodiumtriacetoxyborohydride,calselect?stab; Sodium triacetohydroborate, Triacetohydroborate sodium salt; Sodium; Sodium 1-[(diacetoxyboryl)oxy]ethanolate; Boric acid (H3BO3), diacetyl 1-hydroxyethyl ester, sodium salt (1:1);

Sodium Triacetoxyborohydride CAS 56553-60-7 Storage

Store sodium triacetoxyborohydride in a cool and dry place, away from heat sources and direct sunlight. The ideal storage temperature for sodium triacetoxyborohydride is generally below 25°C (77°F). Avoid extreme temperature fluctuations.

Sodium Triacetoxyborohydride CAS 56553-60-7 Application

1. Reduction of Carbonyl Compounds: Sodium triacetoxyborohydride is frequently employed for the reduction of carbonyl compounds, such as aldehydes and ketones, to their corresponding alcohols. It is especially useful for reducing sensitive or difficult-to-reduce functional groups.
2. Reductive Amination: Sodium triacetoxyborohydride is widely utilized in reductive amination reactions, where it converts carbonyl compounds (aldehydes or ketones) and primary or secondary amines into their corresponding amine products. This reaction is valuable in the synthesis of various pharmaceuticals and fine chemicals.
3. Deoxygenation: Sodium triacetoxyborohydride can be employed to remove oxygen from reaction mixtures or solvents. It is useful for creating anaerobic conditions in certain chemical reactions.
4. Allylation: Sodium triacetoxyborohydride can be utilized as a reducing agent for the allylation of carbonyl compounds. This reaction allows the introduction of allyl groups onto a carbonyl carbon.
5. Miscellaneous Applications: Sodium triacetoxyborohydride may find use in various other organic transformations, such as the reduction of imines, reductive cleavage of cyclic acetals, and the reduction of nitro compounds to amines.