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14691-88-4 Usage

Chemical Properties

Red-Brown Oil

Uses

Different sources of media describe the Uses of 14691-88-4 differently. You can refer to the following data:
1. 4-Amino-TEMPO is useful spin label for studying biological systems and polymers.
2. Useful spin label for studying biological systems, polymers, and as a building block for more elaborate spin labels.

Check Digit Verification of cas no

The CAS Registry Mumber 14691-88-4 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 8 respectively.
Calculate Digit Verification of CAS Registry Number 14691-88:
(7*1)+(6*4)+(5*6)+(4*9)+(3*1)+(2*8)+(1*8)=124
124 % 10 = 4
So 14691-88-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H20N2O/c1-8(2)5-7(10)6-9(3,4)11(8)12/h7,12H,5-6,10H2,1-4H3/p+1

14691-88-4 Well-known Company Product Price

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  • TCI America

  • (A1343)  4-Amino-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical  >97.0%(GC)

  • 14691-88-4

  • 1g

  • 915.00CNY

  • Detail
  • TCI America

  • (A1343)  4-Amino-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical  >97.0%(GC)

  • 14691-88-4

  • 5g

  • 2,650.00CNY

  • Detail
  • Fluka

  • (43967)  4-Amino-TEMPO  for ESR-spectroscopy

  • 14691-88-4

  • 43967-250MG

  • 1,539.72CNY

  • Detail
  • Aldrich

  • (163945)  4-Amino-TEMPO,freeradical  97%

  • 14691-88-4

  • 163945-1G

  • 1,254.24CNY

  • Detail
  • Aldrich

  • (163945)  4-Amino-TEMPO,freeradical  97%

  • 14691-88-4

  • 163945-5G

  • 4,105.53CNY

  • Detail

14691-88-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Amino-Tempo, Free Radical

1.2 Other means of identification

Product number -
Other names 4-Amino-2,2,6,6-tetramethylpiperidine-1-oxyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14691-88-4 SDS

14691-88-4Synthetic route

4-azido-2,2,6,6-tetramethyl-1-piperidinyloxy radical
63697-61-0

4-azido-2,2,6,6-tetramethyl-1-piperidinyloxy radical

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
With ammonium hydroxide; triphenylphosphine In pyridine for 14h; Ambient temperature;97%
Multi-step reaction with 2 steps
1: 86 percent / diethyl ether / Heating
2: 72 percent / aq. ethanol / 10 h / Heating
View Scheme
4-oxo-2,2,6,6-tetramethylpiperidin-oxyl
45985-26-0, 2896-70-0

4-oxo-2,2,6,6-tetramethylpiperidin-oxyl

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
With hydroxyammonium sulfate In sulfuric acid at 6 - 8℃; for 2.5h; electrolysis;90%
With hydrazine hydrate; lithium chloride In methanol Product distribution; electrolysis; other reagent, solvent;80%
With ammonium acetate; sodium cyanoborohydride In methanol at 20℃; for 48h; pH=7; Inert atmosphere; Schlenk technique;76%
4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy
14691-89-5, 136708-39-9

4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
With water; potassium hydroxide In methanol for 96h; Reflux;88%
With potassium hydroxide In methanol; water at 100℃; for 96h; Sealed tube;84%
With potassium hydroxide In methanol; water at 100℃; for 96h; Sealed tube;84%
C27H32N2OP
78140-47-3

C27H32N2OP

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
In ethanol for 10h; Heating;72%
4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE
36768-62-4

4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
With decanesulfonic peracid In chloroform at 19.9℃;45%
With phosphotungstic acid; dihydrogen peroxide In water for 48h; Ambient temperature;
Multi-step reaction with 3 steps
1.1: 197 g / diethyl ether / 3.5 h / 5 - 10 °C
2.1: K2CO3 / H2O / 0.25 h / 25 °C
2.2: 150.8 g / H2O2; sodium tungstate; disodium EDTA / H2O / 73 h
3.1: 49 percent / KOH / H2O / 29 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 95 percent
2: H2O2
3: KOH
View Scheme
Multi-step reaction with 3 steps
1: diethyl ether / 0.5 h / 15 °C
2: dihydrogen peroxide; sodium tungstate (VI) dihydrate; disodium ethylenediamine tetraacetic acid / water / 16 h / 20 °C
3: potassium hydroxide / water / 12 h / Reflux
View Scheme
4-amino-2,2,6,6-tetramethylpiperidin-1-ol
76462-91-4

4-amino-2,2,6,6-tetramethylpiperidin-1-ol

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
With ; sulfuric acid; potassium hexacyanoferrate(III) electrochemical, pH 8-9; Yield given;
4-acetylamino-2,2,6,6-tetramethyl-1-piperidinium acetate
136708-43-5

4-acetylamino-2,2,6,6-tetramethyl-1-piperidinium acetate

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: K2CO3 / H2O / 0.25 h / 25 °C
1.2: 150.8 g / H2O2; sodium tungstate; disodium EDTA / H2O / 73 h
2.1: 49 percent / KOH / H2O / 29 h / Heating
View Scheme
2,2,6,6-Tetramethyl-4-piperidone
826-36-8

2,2,6,6-Tetramethyl-4-piperidone

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH2OH, H2SO4 / electrochemical, Au cathode
2: , potassium ferricyanide, H2SO4 / electrochemical, pH 8-9
View Scheme
Multi-step reaction with 2 steps
1: sodium tungstate (VI) dihydrate; dihydrogen peroxide; ethylenediaminetetraacetic acid / water / 48 h / 20 °C / Darkness
2: sodium cyanoborohydride; ammonium acetate / methanol / 48 h / 20 °C / pH 7 / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 5 steps
1: hydroxylamine hydrochloride; sodium methylate / ethanol; water / 16 h / 20 °C
2: sodium / pentan-1-ol / 3 h / 90 °C
3: diethyl ether / 0.5 h / 15 °C
4: dihydrogen peroxide; sodium tungstate (VI) dihydrate; disodium ethylenediamine tetraacetic acid / water / 16 h / 20 °C
5: potassium hydroxide / water / 12 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: sodium tungstate; dihydrogen peroxide; ethylenediaminetetraacetic acid / water / 48 h / 20 °C / Darkness
2: ammonium acetate; sodium cyanoborohydride / methanol / 48 h / 20 °C / Darkness
View Scheme
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / pyridine / 4 h / 20 °C
2: 98 percent / LiN3 / hexamethylphosphoric acid triamide / 1.5 h / 80 °C
3: 97 percent / (C6H5)3P, conc. NH4OH / pyridine / 14 h / Ambient temperature
View Scheme
4-methanesulfonyl-2,2,6,6-tetramethyl-1-piperidinyloxy radical
35203-66-8

4-methanesulfonyl-2,2,6,6-tetramethyl-1-piperidinyloxy radical

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / LiN3 / hexamethylphosphoric acid triamide / 1.5 h / 80 °C
2: 97 percent / (C6H5)3P, conc. NH4OH / pyridine / 14 h / Ambient temperature
View Scheme
N-(2,2,6,6-tetramethylpiperidin-4-yl)acetamide
40908-37-0

N-(2,2,6,6-tetramethylpiperidin-4-yl)acetamide

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O2
2: KOH
View Scheme
Multi-step reaction with 2 steps
1: dihydrogen peroxide; sodium tungstate (VI) dihydrate; disodium ethylenediamine tetraacetic acid / water / 16 h / 20 °C
2: potassium hydroxide / water / 12 h / Reflux
View Scheme
4-hydroxyimino-2,2,6,6-tetramethylpiperidine
4168-79-0

4-hydroxyimino-2,2,6,6-tetramethylpiperidine

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium / pentan-1-ol / 3 h / 90 °C
2: diethyl ether / 0.5 h / 15 °C
3: dihydrogen peroxide; sodium tungstate (VI) dihydrate; disodium ethylenediamine tetraacetic acid / water / 16 h / 20 °C
4: potassium hydroxide / water / 12 h / Reflux
View Scheme
2,2,6,6-tetramethylpiperidin-1-ol
7031-93-8

2,2,6,6-tetramethylpiperidin-1-ol

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

Conditions
ConditionsYield
With dipotassium peroxodisulfate; sodium hydrogencarbonate In water; acetone at 20℃; Cooling with ice;
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
14691-88-4

4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl

4-isocyanate-2,2,6,6-tetramethylpiperidine-1-oxyl
88418-69-3

4-isocyanate-2,2,6,6-tetramethylpiperidine-1-oxyl

4,4'-(carbonyldiimino)bis(2,2,6,6-tetramethylpiperidinyl-1-oxy)
15180-53-7

4,4'-(carbonyldiimino)bis(2,2,6,6-tetramethylpiperidinyl-1-oxy)

Conditions
ConditionsYield
In diethyl ether100%
In benzene at 20℃; for 1h;88.7%
In dichloromethane for 72h;70%
In chloroform for 0.0833333h; Heating;62 mg

14691-88-4Relevant articles and documents

Immobilization of catalysts in poly(p-xylylene) nanotubes

Hepperle, Johannes A.M.,Mitschang, Fabian,Bier, Anna K.,Dettlaff, Barbara K.,Greiner, Andreas,Studer, Armido

, p. 25976 - 25981 (2013)

This paper describes the immobilization of a TEMPO-derivative and a copper catalyst in ethinyl-functionalized poly(p-xylylene) nanotubes which are readily prepared by the Tubes by Fiber Templates (TUFT) process. Catalyst conjugation to the nanotubes is achieved via the Cu-catalyzed azide alkyne cycloaddition (CuAAC). The TEMPO-functionalized nanotubes are successfully used as recyclable catalysts for oxidation of benzyl alcohol. Recycling studies show that the TEMPO-modified nanotubes can be reused 20 times without loss of catalytic activity. Conjugation of the nanotubes with a bipyridine moiety provides a material that allows for immobilization of metal catalysts. Treatment with a Cu(i)-salt leads to a hybrid material, which shows high activity as a recyclable catalyst in the CuAAC. Recycling experiments reveal that these Cu-nanotubes can be reused for 18 runs.

NEW METHOD OF ELECTROCHEMICAL PREPARATION OF 1-OXYL-2,2,6,6-TETRAMETHYL-4-AMINOPIPERIDINE

Fioshin, M. Ya.,Avrutskaya, I. A.,Bogdanova, N. P.,Kedik, S. A.,Surov, I. I.

, p. 1541 (1983)

-

Use of sodium cyanoborohydride in the preparation of biologically active nitroxides

Rosen

, p. 358 - 360 (1974)

-

EPR Studies of V-ATPase with Spin-Labeled Inhibitors DCC and Archazolid: Interaction Dynamics with Proton Translocating Subunit c

G?lz, Jan Philipp,Bockelmann, Svenja,Mayer, Kerstin,Steinhoff, Heinz-Jürgen,Wieczorek, Helmut,Huss, Markus,Klare, Johann P.,Menche, Dirk

, p. 420 - 428 (2016)

Vacuolar-type H+-ATPases (V-ATPases) have gained recent attention as highly promising anticancer drug targets, and therefore detailed structural analyses and studies of inhibitor interactions are very important research objectives. Spin labeling of the V-ATPase holoenzyme from the tobacco hornworm Manduca sexta and V-ATPase in isolated yeast (Saccharomyces cerevisiae) vacuoles was accomplished by two novel methods involving the covalent binding of a (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) derivative of N,N′-dicyclohexylcarbodiimide (DCC) to the essential glutamate residue in the active site and the noncovalent interaction of a radical analogue of the highly potent inhibitor archazolid, a natural product from myxobacteria. Both complexes were evaluated in detail by electron paramagnetic resonance (EPR) spectroscopic studies and double electron-electron resonance (DEER) measurements, revealing insight into the inhibitor binding mode, dynamics, and stoichiometry as well as into the structure of the central functional subunit c of these medicinally important hetero-multimeric proton-translocating proteins. This study also demonstrates the usefulness of natural product derived spin labels as tools in medicinal chemistry. Near and DEER: Electron paramagnetic resonance (EPR) and double electron-electron resonance (DEER) studies of V-ATPase in complex with spin-labeled inhibitors DCC and archazolid have enabled insight into the noncovalent binding dynamics and analysis of the enzyme′s key functional subunit c. These studies also demonstrate the general utility of natural product derived spin labels as innovative tools for chemical biology.

THE OXIDATION OF SECONDARY AMINES BY ALKANESULFONIC PERACIDS

Safiullin, R. L.,Enikeeva, L. R.,Bukin, I. I.,Mukhametova, G. A.,Shishlov, N. M.,et al.

, p. 1045 - 1047 (1990)

Alkanesulfonic peracids are efficient oxidation agents for the conversion of secondary amines to the corresponding nitroxyl radicals.

Hierarchically structured, blue-emitting polymer hybrids through surface-initiated nitroxide-mediated polymerization and water templated assembly

Leone, Giuseppe,Giovanella, Umberto,Bertini, Fabio,Hoseinkhani, Sajjad,Porzio, William,Ricci, Giovanni,Botta, Chiara,Galeotti, Francesco

, p. 6585 - 6593 (2013)

A facile and robust approach for fabricating structured, blue-emitting polymer hybrids is explored by grafting poly(styrene) incorporating π-conjugated oligo(fluorene) side-chains, to fluoromica silicate layers through surface-initiated nitroxide-mediated polymerization (SI-NMP). It is expected that the polymer intercalation can effectively reduce π-stacking, chain-chain interactions, twists and bends, and interfacial effects, leading to significant difference in the electronic/optoelectronic properties, and improved optical, thermal and chemical stability of the materials. The experimental results indicate that the bottom-up strategy is rational and efficacious. The hybrids exhibit a blue photoluminescence quantum yield (PL-QY) as high as 0.90, even in the solid, which makes the materials appealing for polymer light-emitting devices (PLEDs). The materials also show significantly enhanced thermal, and chemical stabilities with respect to the organic precursors. If processed under specific controlled conditions, the hybrids spontaneously assemble into highly ordered microporous films, where an organization of matter at different length scales is obtained. Since the introduction of surface patterning in the active layer could enhance the extraction of light generated in the device, this hierarchical organization is a promising tool for the further development of optimized hybrid PLEDs.

A Simple Synthesis of 4-Amino-2,2,6,6-tetramethyl-1-piperidinyloxy Radical

Bushmakina, N. G.,Misharin, A. Yu.

, p. 966 (1986)

A simple synthesis of the title compound starting from 4-hydroxy-2,2,6,6-tetramethyl-1-piperidyloxy radical (2) based on sulfonate-azide exchange method is described.

Synthesis and fluorescence properties of six fluorescein-nitroxide radical hybrid-compounds

Sato, Shingo,Endo, Susumu,Kurokawa, Yusuke,Yamaguchi, Masaki,Nagai, Akio,Ito, Tomohiro,Ogata, Tateaki

supporting information, p. 66 - 71 (2016/07/06)

Six fluorescein-nitroxide radical hybrid-compounds (2ab, 3ab, 4, and 5) were synthesized by the condensation of 5- or 6-carboxy-fluorescein and 4-amino-TEMPO (2ab), 5- or 6-aminofluorescein and 4-carboxy-TEMPO (3ab), and fluorescein and 4-carboxy-TEMPO (4), or by reaction of the 3-hydroxyl group of fluorescein with DPROXYL-3-ylmethyl methanesulfonate (5). Fluorescence intensities (around 520 nm) after reduction of the radical increased to 1.43-, 1.38-, and 1.61-folds for 2a, 2b and 3b respectively; 3a alone exhibited a decrease in intensity on reduction. Since 4 was readily solvolyzed in PBS or even methanol to afford fluorescein and 4-carboxy-TEMPO, its fluorescence change could not be measured. Hybrid compound 5 containing an ether-linkage between the fluorescein phenol and 3-hydroxymethyl-DPROXYL hydroxyl centers, was stable and on reduction, showed a maximum increase (3.21-fold) in relative fluorescence intensity in PBS (pH 5.0), despite its remarkably low absolute fluorescence intensity.

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