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296813

Sigma-Aldrich

Sodium cyanoborohydride solution

1.0 M in THF

Synonym(s):

Sodium borocyanohydride, Sodium cyanoborohydride, Sodium cyanotrihydroborate

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About This Item

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

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

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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.

Signal Word

Danger

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

Supplementary Hazards

EUH019

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

-4.0 °F

Flash Point(C)

-20 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sodium cyanoborohydride-a highly selective reducing agent for organic functional groups.
Clinton F.
Synthesis, 3, 135-146 (1975)
Preparation of colloidal gold particles of various sizes using sodium borohydride and sodium cyanoborohydride.
R G DiScipio
Analytical biochemistry, 236(1), 168-170 (1996-04-05)
Radiolabeling of proteins by reductive alkylation with [14C]formaldehyde and sodium cyanoborohydride.
D Dottavio-Martin et al.
Analytical biochemistry, 87(2), 562-565 (1978-07-01)
Heather L Lord et al.
Journal of pharmaceutical and biomedical analysis, 44(2), 506-519 (2007-02-23)
Immunoaffinity solid phase microextraction (SPME) probes have been developed with antibodies specific for the benzodiazepine class of drugs, covalently immobilized to glass rods. This involved both purification of the polyclonal antibodies to isolate the drug-specific fraction, and optimization of the
Labeling of proteins by reductive methylation using sodium cyanoborohydride.
N Jentoft et al.
The Journal of biological chemistry, 254(11), 4359-4365 (1979-06-10)
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