38078-71-6

Basic information

• Product Name: 4-CYANO-TEMPO
• Synonyms: 4-CYANO-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL;4-CYANO-TEMPO;4-CYANO-TEMPO, FREE RADICAL, 97%;Nsc300607;4-Cyano-2,2,6,6-tetraMethylpiperidine 1-Oxyl
• CAS NO: 38078-71-6
• Molecular Formula: C₁₀H₁₇N₂O
• Molecular Weight: 181.25
• Product Categories: Analytical Chemistry;ESR Spectrometry;Spin Labels;Radical Chemistry;Stable Radicals;TEMPO Derivatives
• Mol File: 38078-71-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 145-147 °C(lit.)
• Boiling Point: 294.923 °C at 760 mmHg
• Flash Point: 132.165 °C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 0.000383mmHg at 25°C
• Refractive Index: 1.503
• Storage Temp.: Refrigerator
• Solubility: soluble in Ethanol
• CAS DataBase Reference: 4-CYANO-TEMPO(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANO-TEMPO(38078-71-6)
• EPA Substance Registry System: 4-CYANO-TEMPO(38078-71-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 26-27-28-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 38078-71-6(Hazardous Substances Data)

Usage

Uses

4-Cyano-TEMPO (cas# 38078-71-6) is a compound useful in organic synthesis.

InChI:InChI=1/C10H18N2O/c1-9(2)5-8(7-11)6-10(3,4)12(9)13/h8,13H,5-6H2,1-4H3

Upstream product

• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 826-36-8 2,2,6,6-Tetramethyl-4-piperidone 
• 1048979-86-7 1-hydroxy-4-cyano-2,2,6,6-tetramethylpiperidinium chloride 
• 45985-26-0 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl 

Downstream Products

• 37149-18-1 1-oxyl-4-carboxyl-2,2,6,6-tetramethylpiperidine 

Relevant articles and documents

Suspending Ion Electrocatalysts in Charged Metal–Organic Frameworks to Improve the Conductivity and Selectivity in Electroorganic Synthesis

Electroorganic synthesis is an environmentally friendly alternative to traditional synthetic methods; however, the application of this strategy is heavily hindered by low product selectivity. Metal–organic frameworks (MOFs) exhibit high selectivity in numerous catalytic reactions; however, poor conductivity heavily limits the application of MOFs in electroorganic synthesis. To realize the electrocatalytic application of MOFs in selective electroorganic synthesis, a practically applicable strategy by suspending ion electrocatalysts in charged MOFs is herein reported. This approach could markedly improve the product selectivity in electroorganic synthesis. In the electrocatalytic oxidative self-coupling of benzylamine experiments, the imine product selectivity is markedly improved from 61.3 to 94.9 %, when the MOF-based electrocatalyst is used instead of the corresponding homogeneous electrocatalyst under the identical conditions. Therefore, this work opens a new route to improve the product selectivity in electroorganic synthesis.

Kinetics and thermodynamics of reversible disproportionation-comproportionation in redox triad oxoammonium cations - Nitroxyl radicals - Hydroxylamines

Kinetics and equilibrium of the acid-catalyzed disproportionation of cyclic nitroxyl radicals R2NO· to oxoammonium cations R2NO+ and hydroxylamines R2NOH is defined by redox and acid-base properties of these compounds. In a recent work (J. Phys. Org. Chem. 2014, 27, 114-120), we showed that the kinetic stability of R2NO· in acidic media depends on the basicity of the nitroxyl group. Here, we examined the kinetics of the reverse comproportionation reaction of R2NO+ and R2NOH to R2NO· and found that increasing in -I-effects of substituents greatly reduces the overall equilibrium constant of the reaction K4. This occurs because of both the increase of acidity constants of hydroxyammonium cations K3H+ and the difference between the reduction potentials of oxoammonium cations ER2NO+/R2NO· and nitroxyl radicals ER2NO·/R2NOH. pH dependences of reduction potentials of nitroxyl radicals to hydroxylamines E1/3σ and bond dissociation energies D(O-H) for hydroxylamines R2NOH inwater were determined. For a wide variety of piperidine- and pyrrolidine-1-oxyls values of pK3H+ and ER2NO+/R2NO· correlate with each other, as well aswith the equilibriumconstants K4 and the inductive substituent constants ωI. The correlations obtained allowprediction of the acid-base and redox characteristics of redox triads R2NO·-R2NO+-R2NOH.

Highly efficient polarizing agents for dynamic nuclear polarization

The invention relates to compounds of general formula (I) wherein X is C=O or SO2, M is NR2 or O, and Q1 and Q2 are nitroxide-containing radicals, and their use as a Dynamic Nuclear Polarization (DNP) agent for polarizing an NMR-active spin of a nucleus of an analyte in Nuclear Magnetic Resonance (NMR) spectroscopy.