296813

Sodium cyanoborohydride solution

1.0 M in THF

• Synonym(s): Sodium borocyanohydride, Sodium cyanoborohydride, Sodium cyanotrihydroborate
• Linear Formula: NaBH₃CN
• CAS Number: 25895-60-7
• Molecular Weight: 62.84
• MDL number: MFCD00003516
• UNSPSC Code: 12352306
• PubChem Substance ID: 24857879
• NACRES: NA.22

Properties

• Quality Level: 200
• reaction suitability: reagent type: reductant
• concentration: 1.0 M in THF
• solubility: THF: soluble(lit.); alcohol: soluble(lit.); hydrocarbons: insoluble(lit.); water: soluble(lit.)
• density: 0.915 g/mL at 25 °C
• SMILES string: [Na+].[H][B-]([H])([H])C#N
• InChI: 1S/CH3BN.Na/c2-1-3;/h2H3;/q-1;+1
• InChI key: CVDUGUOQTVTBJH-UHFFFAOYSA-N

Description

General description

Sodium cyanoborohydride is a versatile reducing agent stable in aqueous solution at pH 7.2. It is a weaker reducing agent as compared to NaBH₄. It effectively reduces Schiff bases. NaCNBH₄ participates in the reductive methylation for the efficient and selective conversion of the e-amino groups of lysyl residues in proteins to the mono- and dimethyl derivatives.

Application

Reactant for:

• Direct conversion of heterocyclic aldehydes to esters (oxidizing behavior)
• Reductive amination reactions
• Intramolecular reductive cyclization reactions
• Reductions reactions
• Preparation of dicyanoborate-based ionic liquids as hypergolic fluids for bipropellants

Sodium cyanoborohydride may be used in the following studies:

• As reducing agent for the in vitro radiolabeling of proteins by reductive alkylation.
• Reduction of aldehydes and ketones.
• Selective deoxygenation of aldehydes and ketones.
• Preparation of colloidal gold particles of varying sizes.

Safety Information

• pictograms: GHS02,GHS06,GHS08,GHS05,GHS09
• signalword: Danger
• hcodes: H225,H260,H301 + H311 + H331,H314,H335,H336,H351,H410
• pcodes: P210 - P231 + P232 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 1
• target_organs: Central nervous system, Respiratory system
• supp_hazards: EUH019
• Storage Class: 4.3 - Hazardous materials which set free flammable gases upon contact with water
• wgk_germany: WGK 3
• flash_point_f: -4.0 °F
• flash_point_c: -20 °C