Sodium Triacetoxyborohydride

Abstract

[56553-60-7] C6H10BNaO6 (MW 211.96) InChI = 1S/C6H10BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h7H,1-3H3;/q-1;+1 InChIKey = HHYFEYBWNZJVFQ-UHFFFAOYSA-N (the prototype of a class of NaBH(OCOR)3 reagents that are selective reducing agents for a number of functional groups1 and heterocycles;1 alkylation of amines;1-4 hydroboration1) Physical Data: mp 116–120 °C (dec); the related NaBH3OAc has not been fully characterized. Solubility: NaBH(OAc)3 and related acyloxyborohydrides are rapidly destroyed by H2O and protic solvents; H2 is liberated. Cosolvents that have been employed are benzene, toluene, THF, dioxane, CH2Cl2, ClCH2CH2Cl. Form Supplied in: NaBH(OAc)3 and the related Tetramethylammonium Triacetoxyborohydride are commercially available as colorless powders. Preparative Method: NaBH(OAc)3 and NaBH3OAc can be easily prepared in situ from the appropriate amount of acetic acid and NaBH4. Analysis of Reagent Purity: NaBH(OAc)3 has been characterized by elemental analysis, IR, and 1H, 13C, and 11B NMR. Handling, Storage, and Precautions: because H2 is liberated during the preparation of these reagents, all handling and storage of acyloxyborohydrides should take place under an inert atmosphere.