4-Amino-2,2,6,6-tetramethylpiperidine 1-oxide

Base Information

• Chemical Name: 4-Amino-2,2,6,6-tetramethylpiperidine 1-oxide
• CAS No.: 14691-88-4
• Deprecated CAS: 125342-82-7,26947-98-8,78774-22-8,1818888-12-8,26947-98-8,78774-22-8
• Molecular Formula: C9H19N2O
• Molecular Weight: 173.279
• Hs Code.: 29333990
• European Community (EC) Number: 238-738-2
• DSSTox Substance ID: DTXSID0065808
• Nikkaji Number: J228.180E
• ChEMBL ID: CHEMBL607022
• Mol file: 14691-88-4.mol

Synonyms:2,2,6,6-tetramethyl-4-aminopiperidine-1-oxyl;2,2,6,6-tetramethylpiperidine-N-oxyl-4-amine;4-amino-2,2,6,6-tetramethyl-1-piperidinyloxy;4-amino-2,2,6,6-tetramethylpiperidin--1-oxyl;4-amino-2,2,6,6-tetramethylpiperidine oxide;4-amino-TEMPO;4-AmTEMPO;A-TEMPO;tempamine

Chemical Property of 4-Amino-2,2,6,6-tetramethylpiperidine 1-oxide

Chemical Property:

• Appearance/Colour: Red-brown oil
• Vapor Pressure: 0.00968mmHg at 25°C
• Melting Point: 37-39 °C
• Refractive Index: 1.4480 (estimate)
• Boiling Point: 98 °C / 4mmHg
• Flash Point: 39 °C
• PSA: 29.26000
• Density: 0.9977 (rough estimate)
• LogP: 1.95040
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 171.149738234
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

4-Amino-2,2,6,6-tetramethylpiperidinyloxy ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22-34
• Safety Statements: 26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amine Oxides
• Canonical SMILES: CC1(CC(CC(N1[O])(C)C)N)C
• Uses: 4-Amino-TEMPO is useful spin label for studying biological systems and polymers. Useful spin label for studying biological systems, polymers, and as a building block for more elaborate spin labels.

Technology Process of 4-Amino-2,2,6,6-tetramethylpiperidine 1-oxide

There total 23 articles about 4-Amino-2,2,6,6-tetramethylpiperidine 1-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

4-azido-2,2,6,6-tetramethyl-1-piperidinyloxy radical (63697-61-0) → 4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl (14691-88-4,78774-22-8)

Guidance literature:

With ammonium hydroxide; triphenylphosphine; In pyridine; for 14h; Ambient temperature;

DOI:10.1055/s-1986-31841

Reference yield: 92.0%

4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl (14691-89-5) → tempamine (14691-88-4)

Guidance literature:

With potassium hydroxide; In water; for 36h; Reflux;

DOI:10.1021/jm101232t

Reference yield: 90.0%

4-oxo-2,2,6,6-tetramethylpiperidin-oxyl (45985-26-0,2896-70-0) → 4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl (14691-88-4,78774-22-8)

Guidance literature:

With hydroxyammonium sulfate; In sulfuric acid; at 6 - 8 ℃; for 2.5h; electrolysis;

DOI:10.1007/BF00954393

upstream raw materials:

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

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

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

C₂₇H₃₂N₂OP

Downstream raw materials:

bis(p-nitrophenyl) 1-oxy-2,2,6,6-tetramethyl-4-piperidinyl phosphoramidate

triethylamine hydrochloride

C₁₅H₂₇N₂O₄

N(4',-(2',2',6',6'-tetramethylpyperidine-1-oxyl)-3,5-dinitro-4-chloro)benzamide

Refernces

• 1、 G?lz, Jan Philipp,NejatyJahromy, Yaser,Bauer, Mirko,Muhammad, Ashraf,Schnakenburg, Gregor,Grimme, Stefan,Schiemann, Olav,Menche, Dirk. "Design, Synthesis, EPR-Studies and Conformational Bias of Novel Spin-Labeled DCC-Analogues for the Highly Regioselective Labeling of Aliphatic and Aromatic Carboxylic Acids". . p. 9591 - 9598. Retrieved 2016.
• 2、 Braslau, Rebecca,Rivera, Frank,Lilie, Erin,Cottman, Mariellen. "Urushiol detection using a profluorescent nitroxide". . p. 238 - 245. Retrieved 2013.
• 3、 Sultani, Haider N.,Haeri, Haleh H.,Hinderberger, Dariush,Westermann, Bernhard. "Spin-labelled diketopiperazines and peptide-peptoid chimera by Ugi-multi-component-reactions". . p. 11336 - 11341. Retrieved 2016.
• 4、 Schattling, Philipp,Jochum, Florian D.,Theato, Patrick. "Multi-responsive copolymers: Using thermo, light- and redox stimuli as three independent inputs towards polymeric information processing". . p. 8859 - 8861. Retrieved 2011.
• 5、 Nakatsuji,Mizumoto,Kitamura,Akutsu,Yamada. "Preparation and properties of biphenyl and cholesterol derivatives with nitroxide radicals". . p. 33 - 40. Retrieved 2001.
• 6、 Misharin et al.. "". . . Retrieved 1974.
• 7、 -. "Nitrogen-oxygen stable free radical with aggregation-induced emission function, and preparation method thereof". Paragraph 0022-0023. . Retrieved 2020/03/03.