Sodium triacetoxyborohydride, 95%

Name: Sodium triacetoxyborohydride, 95%
SKU: B22060.14

CAS: 56553-60-7 | C6H10BNaO6 | 211.94 g/mol

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Catalog number B22060.14

also known as B22060-14

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25 g

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Chemical Identifiers

CAS56553-60-7

IUPAC Namesodium bis(acetyloxy)boranuidyl acetate

Molecular FormulaC6H10BNaO6

InChI KeyHHYFEYBWNZJVFQ-UHFFFAOYSA-N

SMILES[Na+].CC(=O)O[BH-](OC(C)=O)OC(C)=O

Specifications

Specification Sheet

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Appearance (Color)White

Assay from Supplier's CofA≥94.0%

Sodium triacetoxyborohydride is used as a reagent in reductive amination of ketones, aldehydes and lactamization of carbonyl compounds with amines. It also serves as a reducing agent in organic synthesis.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Sodium triacetoxyborohydride is used as a reagent in reductive amination of ketones, aldehydes and lactamization of carbonyl compounds with amines. It also serves as a reducing agent in organic synthesis.

Solubility
Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride.

Notes
Moisture sensitive. Incompatible with strong oxidizing agents, water, alcohols and acids.

RUO – Research Use Only

General References:

Selective reducing agent; review: Org. Prep. Proced. Int., 17, 317 (1985). Reduces aldehydes in the presence of ketones: J. Chem. Soc., Chem. Commun., 535 (1975). For stereoselective reduction of ketones in AcOH, see: Tetrahedron Lett., 273 (1983). Reduces ß-hydroxy ketones diastereoselectively to anti-diols: J. Am. Chem. Soc., 110, 3560 (1988), and cyclic ß-enamino esters selectively to the cis-amino esters: J. Org. Chem., 59, 5328 (1994); Tetrahedron: Asymmetry, 5, 1455 (1994).
Excellent reagent for reductive amination of aldehydes and ketones with a wide variety of amines: J. Org. Chem., 61, 3849 (1996); Tetrahedron Lett., 37, 3977 (1996); review: A.C.S. Symp. Ser., 641, 201 (1996).
Tahara, Y. K.; Ito, M.; Kanyiva, K. S.; Shibata, T. Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step. Chem. Eur. J. 2015, 21 (32), 11340-11343.
Kang, B.; Oh, J. A.; Lee, J. Y.; Rhim, H.; Yune, T. Y.; Choo, H. Y. P. 3-Benzamides and 3, 4, 5-trimethoxyphenyl amines as calcium channel blockers. Bioorg. Med. Chem 2015, 23 (18), 6166-6172.