316393

Sodium triacetoxyborohydride

97%

• Synonym(s): STAB
• Linear Formula: (CH₃COO)₃BHNa
• CAS Number: 56553-60-7
• Molecular Weight: 211.94
• Beilstein: 4047608
• MDL number: MFCD00012211
• UNSPSC Code: 12352302
• PubChem Substance ID: 24859012
• NACRES: NA.22

Properties

• Assay: 97%
• reaction suitability: reagent type: reductant
• mp: 116-120 °C (dec.) (lit.)
• SMILES string: [Na+].CC(=O)O[BH-](OC(C)=O)OC(C)=O
• InChI: 1S/C6H10BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h7H,1-3H3;/q-1;+1
• InChI key: HHYFEYBWNZJVFQ-UHFFFAOYSA-N

Description

General description

Sodium triacetoxyborohydride (NaBH(OAc)3) is particularly effective in reductive aminations due to its large scope, mildness, and selectivity. It is preferred to sodium cyanoborohydride(NaBH3CN) in many applications due to reduced toxicity of the side products formed, and better yields and reproducibility during synthesis.

Application

Sodium triacetoxyborohydride or [NaBH(OAc)₃] can be used as a reagent:

• In the reductive amination of ketones and aldehydes.
• To prepare N-benzyl-γ-valerolactam by reacting with methyl 4-oxopentanoate and benzylamine via reductive amination/lactamization.
• To reduce imines and enamines to corresponding amines.
• To reduce quinolines and isoquinolines to corresponding tetrahydro derivatives.
• In the hydroboration of alkenes.
• To synthesize nitroxide biradicals for creating high relaxivity terminal groups linkage to dendrimers.

Applications using Sodium triacetoxyborohydride

Safety Information

• Pictograms: GHS02,GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H228,H260,H302,H318,H360FD
• Precautionary Statements: P210 - P231 + P232 - P280 - P301 + P312 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Sol. 1 - Repr. 1B - Water-react 1
• Supplementary Hazards: EUH014
• Storage Class Code: 4.3 - Hazardous materials which set free flammable gases upon contact with water
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable