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Merck
CN

296945

Sodium cyanoborohydride solution

5.0 M in 1 M NaOH

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:
24857889
UNSPSC Code:
12352306
MDL number:
MFCD00003516

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Product Name

Sodium cyanoborohydride solution, 5.0 M in 1 M NaOH

InChI

1S/CH3BN.Na/c2-1-3;/h2H3;/q-1;+1

SMILES string

[Na+].[H][B-]([H])([H])C#N

InChI key

CVDUGUOQTVTBJH-UHFFFAOYSA-N

reaction suitability

reagent type: reductant

concentration

5.0 M in 1 M NaOH

density

1.083 g/mL at 25 °C

Quality Level

200

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Related Categories

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

General description

Sodium cyanoborohydride is a selective, mild reducing reagent for a number of functional groups such as aldehydes, ketones, acetals, epoxides and imines.

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Met. Corr. 1 - Skin Corr. 1B

supp_hazards

EUH032

Storage Class

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBQ6328
SHBP0470
SHBN8928
SHBP9520
SHBP4275

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e-EROS Encyclopedia of Reagents for Organic Synthesis (2016)
Franklin Afinjuomo et al.
Pharmaceutics, 11(5) (2019-05-28)
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Chika Wakita et al.
The Journal of biological chemistry, 284(42), 28810-28822 (2009-08-21)
4-Hydroxy-2-nonenal (HNE), a major racemic product of lipid peroxidation, preferentially reacts with cysteine residues to form a stable HNE-cysteine Michael addition adduct possessing three chiral centers. Here, to gain more insight into sulfhydryl modification by HNE, we characterized the stereochemical
Shinsuke Sando et al.
Bioorganic & medicinal chemistry letters, 13(16), 2633-2636 (2003-07-23)
We report here that unprotected carbohydrates (maltose, lactose, cellobiose, and maltoheptaose) can be attached to the aminoalkylated oligonucleotides under mild reductive-amination conditions (aqueous borate buffer, pH 8.0, NaBH(3)CN, 60 degrees C) without notable side reactions. Quadruplex-forming G-rich oligonucleotide, 5'-aminoalkyl d(TGGGGT)
Jue-Liang Hsu et al.
Electrophoresis, 27(18), 3652-3660 (2006-08-24)
Stable-isotope labeling coupled with liquid-phase separation and MS analysis is a powerful technique for comparative proteomics. We developed a dimethyl labeling strategy (Anal. Chem. 2003, 75, 6843-6852 and J. Proteome Res. 2005, 4, 101-108) to label peptide N-terminus and epsilon-amino
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