2154-70-3

Basic information

• Product Name: 3-CYANO-2,2,5,5-TETRAMETHYL-1-PYRROLIDINYLOXY
• Synonyms: 3-CYANO-PROXYL;3-CYANO-2,2,5,5-TETRAMETHYL-1-PYRROLIDINYLOXY;3-cyano-2,2,5,5-tetramethyl-1-pyrrolidinyl-n-oxyl;3-CYANO-PROXYL, FREE RADICAL;3-cyano-2,2,5,5-tetramethyl-1-pyrrolidinyloxy, free radical
• CAS NO: 2154-70-3
• Molecular Formula: C₉H₁₅N₂O
• Molecular Weight: 167.23
• Mol File: 2154-70-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 31-33 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: 113 °C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.00131mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-CYANO-2,2,5,5-TETRAMETHYL-1-PYRROLIDINYLOXY(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANO-2,2,5,5-TETRAMETHYL-1-PYRROLIDINYLOXY(2154-70-3)
• EPA Substance Registry System: 3-CYANO-2,2,5,5-TETRAMETHYL-1-PYRROLIDINYLOXY(2154-70-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 2154-70-3(Hazardous Substances Data)

Usage

Uses

3-Cyano-PROXYL is a stable free radical that can be used in the ESR technique as a nitroxide standard:For the estimation of relative concentrations of the spin adducts of 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) with ·OH and O2.- radicals.For the determination of free radicals present in an aqueous cigarette tar extract.

General Description

Spin label

InChI:InChI=1/C9H16N2O/c1-8(2)5-7(6-10)9(3,4)11(8)12/h7,12H,5H2,1-4H3/t7-/m1/s1

Upstream product

• 46147-12-0 3-carbamoyl-2,2,5,5-tetramethylpyrrolidin-1-yloxy 

Relevant articles and documents

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.