316393

Sodium triacetoxyborohydride

>95%

• Synonym(s): STAB
• Linear Formula: (CH₃COO)₃BHNa
• CAS Number: 56553-60-7
• Molecular Weight: 211.94
• UNSPSC Code: 12352302
• NACRES: NA.22
• PubChem Substance ID: 24859012
• MDL number: MFCD00012211
• Beilstein/REAXYS Number: 4047608
• Assay: >95%

Properties

• Quality Level: 200
• assay: >95%
• reaction suitability: reagent type: reductant
• greener alternative product score: old score: 5; new score: 1; Find out more about DOZN™ Scoring
• greener alternative product characteristics: Waste Prevention; Design for Energy Efficiency; Use of Renewable Feedstocks; Learn more about the Principles of Green Chemistry.
• sustainability: Greener Alternative Product
• mp: 116-120 °C (dec.) (lit.)
• greener alternative category: Re-engineered
• 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

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives. This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Design for Energy Efficiency” and “Use of Renewable Feedstocks”. Click here to view its DOZN scorecard.

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
• signalword: Danger
• hcodes: H228,H260,H302,H318,H360FD
• pcodes: P210 - P231 + P232 - P280 - P301 + P312 - P305 + P351 + P338 - P308 + P313
• supp_hazards: EUH014
• Storage Class: 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
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Sol. 1 - Repr. 1B - Water-react. 1