14691-89-5 Usage
Description
4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl (4-ACETAMIDO-TEMPO) is a stable free radical compound that undergoes one-electron oxidation and reduction reactions. It is known for its ability to catalyze the oxidation of alcohols to carbonyl compounds in the presence of TsOH (p-toluenesulfonic acid). The reaction products can be analyzed using 1H, 13C, and 15N NMR spectral data.
Uses
Used in Chemical Synthesis:
4-ACETAMIDO-TEMPO is used as a catalyst for the oxidation of alcohols to carbonyl compounds in the presence of TsOH. This application is particularly useful in the synthesis of various organic compounds, as it provides a selective and efficient method for converting alcohols to their corresponding carbonyl compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-ACETAMIDO-TEMPO is used as a catalyst for the oxidation of alcohols to carbonyl compounds, which is a crucial step in the synthesis of various drugs and drug intermediates. Its ability to selectively oxidize alcohols without causing over-oxidation makes it a valuable tool in the development of new pharmaceuticals.
Used in Material Science:
4-ACETAMIDO-TEMPO can be employed in the field of material science for the synthesis of novel materials with unique properties. The selective oxidation of alcohols to carbonyl compounds can be utilized to create new polymers, coatings, and other materials with specific characteristics, such as improved stability or enhanced reactivity.
Used in Environmental Applications:
4-ACETAMIDO-TEMPO can be used in environmental applications for the oxidation of alcohols to carbonyl compounds, which can help in the degradation of pollutants and the treatment of wastewater. Its selective oxidation properties make it a promising candidate for the development of new environmental technologies and processes.
Used in Analytical Chemistry:
In analytical chemistry, 4-ACETAMIDO-TEMPO can be used as a reagent for the detection and quantification of alcohols. Its ability to selectively oxidize alcohols to carbonyl compounds can be exploited in the development of new analytical methods and techniques for the identification and measurement of alcohols in various samples, such as biological fluids, environmental samples, and industrial products.
Purification Methods
Dissolve the 1-oxyl in CH2Cl2, wash it with saturated K2CO3, then saturated aqueous NaCl, dry (Na2SO4), filter and evaporate. The red solid is recrystallised from aqueous MeOH, m 147.5o. [Ma & Bobbitt J Org Chem 56 6110 1991, Rozantsev & Kokhanov Bull Acad Sci USSR, Div Chem Sci 15 1422 1966, Beilstein 22/8 V 174.]
Check Digit Verification of cas no
The CAS Registry Mumber 14691-89-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,6,9 and 1 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 14691-89:
(7*1)+(6*4)+(5*6)+(4*9)+(3*1)+(2*8)+(1*9)=125
125 % 10 = 5
So 14691-89-5 is a valid CAS Registry Number.
InChI:InChI=1/C11H22N2O2/c1-8(14)12-9-6-10(2,3)13(15)11(4,5)7-9/h9,15H,6-7H2,1-5H3,(H,12,14)
14691-89-5Relevant articles and documents
Preparation of Some Homologous TEMPO Nitroxides and Oxoammonium Salts; Notes on the NMR Spectroscopy of Nitroxide Free Radicals; Observed Radical Nature of Oxoammonium Salt Solutions Containing Trace Amounts of Corresponding Nitroxides in an Equilibrium Relationship
Bobbitt, James M.,Eddy, Nicholas A.,Cady, Clyde X.,Jin, Jing,Gascon, Jose A.,Gelpí-Dominguez, Svetlana,Zakrzewski, Jerzy,Morton, Martha D.
, p. 9279 - 9290 (2017/09/22)
Three new homologous TEMPO oxoammonium salts and three homologous nitroxide radicals have been prepared and characterized. The oxidation properties of the salts have been explored. The direct 13C NMR and EPR spectra of the nitroxide free radicals and the oxoammonium salts, along with TEMPO and its oxoammonium salt, have been successfully measured with little peak broadening of the NMR signals. In the spectra of all ten compounds (nitroxides and corresponding oxoammonium salts), the carbons in the 2,2,6,6-tetramethylpiperidine core do not appear, implying paramagnetic properties. This unpredicted overall paramagnetism in the oxoammonium salt solutions is explained by a redox equilibrium as shown between oxoammonium salts and trace amounts of corresponding nitroxide. This equilibrium is confirmed by electron interchange reactions between nitroxides with an N-acetyl substituent and oxoammonium salts with longer acyl side chains.
Selective Aromatic C-H Hydroxylation Enabled by η6-Coordination to Iridium(III)
D'Amato, Erica M.,Neumann, Constanze N.,Ritter, Tobias
, p. 4626 - 4631 (2015/10/06)
We report an aromatic C-H hydroxylation protocol in which the arene is activated through η6-coordination to an iridium(III) complex. η6-Coordination of the arene increases its electrophilicity and allows for high positional selectivity of hydroxylation at the site of least electron density. Through investigation of intermediate η5-cyclohexadienyl adducts and arene exchange reactions, we evaluate incorporation of arene π-activation into a catalytic cycle for C-H functionalization.
Photolabile protecting groups for nitroxide spin labels
Seven, Ibrahim,Weinrich, Timo,Graenz, Markus,Gruenewald, Christian,Bruess, Silke,Krstic, Ivan,Prisner, Thomas F.,Heckel, Alexander,Goebel, Michael W.
, p. 4037 - 4043 (2014/07/08)
Nitroxide spin labels can be protected against critical conditions of DNA/RNA or peptide synthesis by reduction and alkylation with light-sensitive groups such as nitrobenzyl- or aminocoumarins. High chemical stability qualifies tetraethylisoindoline 5 an