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296813

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
NACRES:
NA.22
PubChem Substance ID:
24857879
UNSPSC Code:
12352306
MDL number:
MFCD00003516
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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

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

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.
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

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signalword

Danger

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

flash_point_f

-4.0 °F

flash_point_c

-20 °C

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

Regulatory Information

危险化学品

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN7864
SHBJ9547
SHBF6588V
65896PMV
65896PM

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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)
Selective deoxygenation of ketones and aldehydes including hindered systems with sodium cyanoborohydride.
Hutchins RO, et al.
Journal of the American Chemical Society, 95(11), 3662-3668 (1973)
Sodium cyanoborohydride-a highly selective reducing agent for organic functional groups.
Clinton F.
Synthesis, 3, 135-146 (1975)
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Global Trade Item Number

SKUGTIN
296813-PZ04061823810357
296813-100ML04061826656556
296813-800ML04061838126368