14691-89-5

Basic information

• Product Name: 4-ACETAMIDO-TEMPO
• Synonyms: 4-(acetylamino)-2,2,6,6-tetramethyl-1-Piperidinyloxy;4-Acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl;4-Acetamido-2,2,6,6-tetramethylpiperidinyloxy;N-(1-Hydroxy-2,2,6,6-tetramethyl-4-piperidinyl)acetamide;2,2,6,6-TETRAMETHYL-4-ACETAMIDO-1-PIPERIDINYLOXY;2,2,6,6-TETRAMETHYL-4-ACETAMIDOPIPERIDINE-1-OXYL;4-ACETYLAMINO-2,2,6,6-TETRAMETHYLPIPERIDIN-1-OXYL;4-ACETYLAMINO-2,2,6,6-TETRAMETHYLPIPERIDINE-N-OXYL
• CAS NO: 14691-89-5
• Molecular Formula: C₁₁H₂₁N₂O₂
• Molecular Weight: 213.3
• EINECS: 423-840-3
• Product Categories: Piperidine;Analytical Chemistry;ESR Spectrometry;Oxidation;Spin Labels;Synthetic Organic Chemistry;Radical Chemistry;Stable Radicals;TEMPO Derivatives
• Mol File: 14691-89-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 143-145 °C(lit.)
• Boiling Point: 353.29°C (rough estimate)
• Flash Point: 176.8 °C
• Appearance: Orange-red crystalline powder
• Density: 1.0451 (rough estimate)
• Vapor Pressure: 1.9E-06mmHg at 25°C
• Refractive Index: 1.4620 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in ethanol, acetone, acetonitrile, methylene chloride. I
• BRN: 3546225
• CAS DataBase Reference: 4-ACETAMIDO-TEMPO(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETAMIDO-TEMPO(14691-89-5)
• EPA Substance Registry System: 4-ACETAMIDO-TEMPO(14691-89-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-36/37
• Safety Statements: 26-36-24/25-22
• WGK Germany: 1
• F: 9
• TSCA: Yes
• Hazardous Substances Data: 14691-89-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 14691-89-5 differently. You can refer to the following data:
1. 4-Acetamido-TEMPO, free radical oxidizes alcohols to carbonyl compounds in the presence of TsOH.
2. Oxidizes alcohols to carbonyl compounds in the presence of TsOH.

General Description

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl undergoes one-electron oxidation and reduction reactions. Reaction products were analyzed by 1H, 13C and 15N NMR spectral data.

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.]

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)

Upstream product

• 40908-37-0 N-(2,2,6,6-tetramethylpiperidin-4-yl)acetamide 
• 36768-62-4 4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE 
• 4168-79-0 4-hydroxyimino-2,2,6,6-tetramethylpiperidine 
• 136708-43-5 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinium acetate 
• 73322-05-1 4-acetamino-1H-perdeutero-2,2,6,6-tetramethylpiperidine 
• 826-36-8 2,2,6,6-Tetramethyl-4-piperidone 
• 1620751-78-1 N-[2,2,6,6-tetramethyl-1-(2-nitrobenzyloxy)piperidin-4-yl]acetamide 
• 110-89-4 piperidine 
• 201415-38-5 5-phenylbenzoxazole 
• 14691-88-4 4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl 
• 64-19-7 acetic acid 
• 136708-42-4 4-(acetylamino)-2,2,6,6-tetramethyl-1-hydroxy-piperidinium p-toluenesulfonate 

Downstream Products

• 14691-88-4 tempamine 
• 342630-78-8 5'-dimethoxytrityl-N₄-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine 
• 159550-20-6 5'-dimethoxytrityl-N₄-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxycytidine 
• 342630-68-6 3',5'-diisobutyryl-2-isobutyramido-N6-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxyadenosine 
• 342630-70-0 5'-dimethoxytrityl-2-isobutyramido-N₆-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxyadenosine 
• 342630-72-2 5'-dimethoxytrityl-2-isobutyramido-N₆-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)-2'-deoxyadenosine-3'-(2-cyanoethyl-N,Ndiisopropyl) phosphoramidite 
• 1350920-13-6 4-acetamido-2,2,6,6-tetramethylpiperidine-N-hydroxyammonium tetrafluoroborate 
• 14691-88-4 4-amino-2,2,6,6-tetramethylpiperidinyloxy 
• 122586-91-8 N-(1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)acetamide 

Relevant 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

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)

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

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