Tempone

Base Information

• Chemical Name: Tempone
• CAS No.: 2896-70-0
• Deprecated CAS: 26841-66-7,70939-26-3,1169497-70-4,1818888-13-9,2325667-65-8,1169497-70-4
• Molecular Formula: C₉H₁₆NO₂
• Molecular Weight: 170.232
• Hs Code.: 29333990
• European Community (EC) Number: 220-778-7
• UNII: 7W1863PEH5
• DSSTox Substance ID: DTXSID4044905
• Nikkaji Number: J162G,J2.763.955K
• ChEMBL ID: CHEMBL606972
• Mol file: 2896-70-0.mol

Synonyms:2,2,6,6-Tetramethyl-4-oxopiperidine-1-oxyl;TAN;Tempone;Triacetoneamine N Oxyl;Triacetoneamine-N-Oxyl

Chemical Property of Tempone

Chemical Property:

• Appearance/Colour: orange crystalline powder
• Vapor Pressure: 2.254Pa at 25℃
• Melting Point: 33-38 ºC
• Refractive Index: 1.4640 (estimate)
• Boiling Point: 257.5°Cat760mmHg
• Flash Point: 109.5°C
• PSA: 20.31000
• Density: 1.02g/cm³
• LogP: 1.49190
• Storage Temp.: 0-6°C
• Water Solubility.: Soluble in water (partly), acetone, DMSO, 100% ethanol, and diethylether. Insoluble in water.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 170.118103753
• Heavy Atom Count: 12
• Complexity: 189

Purity/Quality:

98% ^*data from raw suppliers

4-Oxo-TEMPO ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CC(=O)CC(N1[O])(C)C)C
• Description: 2,2,6,6-Tetramethylpiperidin-1-oxyl (TEMPO) is a stable radical that will react with reactive oxygen species (ROS). This conversion, followed by ESR, provides an indirect way to monitor ROS production in biological systems. TEMPONE is the 4-oxo derivative of TEMPO. In addition to possible uses as a spin trap, this nitroxyl radical can be used in hydrogen transfer experiments and as a polarizing agent in dynamic nuclear polarization NMR spectroscopy. TEMPONE and other nitroxyl radicals have also been shown to reduce mean arterial pressure in spontaneously hypertensive rats when administered intravenously.
• Uses: A spin label for ESR studies Free-radical nitroxide spin probe typically used for:Redox sources for anodes in lithium secondary batteriesFree-radical biological studiesRadical spin-trappingElectron paramagnetic resonance studiesPolymer chemisty and synthesis applications

Technology Process of Tempone

There total 33 articles about Tempone 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: 99.0%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl (45985-26-0,2896-70-0)

Guidance literature:

With oxone; tetrabutylammomium bromide; potassium hydroxide; In dichloromethane; water; acetone; at 0 ℃; for 3h; pH=7.5 - 8; aq. phosphate buffer;

DOI:10.1016/j.tet.2009.04.078

Reference yield: 98.0%

2,2,6,6-tetramethylpiperidin-4-one hydrochloride (33973-59-0) → 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl (45985-26-0,2896-70-0)

Guidance literature:

With sodium tungstate; dihydrogen peroxide; In water; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)92284-7

Reference yield: 97.0%

1-hydroxy-2,2,6,6-tetramethyl-piperidin-4-one (3637-11-4) → 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl (45985-26-0,2896-70-0)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; for 0.25h;

DOI:10.1007/BF00957948

upstream raw materials:

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

1-hydroxy-2,2,6,6-tetramethyl-piperidin-4-one

1,3,5-triphenylverdazyl

2-(p-tolyl)-4,6-diphenyl-3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yl

Downstream raw materials:

3-bromo-2,2,5,5-tetramethyl-Δ³-pyrrolin-1-oxyl

3,4-dibromo-2,2,5,5-tetramethyl-Δ³-pyrrolin-1-oxyl

3-bromo-4-methoxycarbonyl-2,2,5,5-tetramethyl-Δ³-pyrrolin-1-oxyl

1-hydroxy-2,2,6,6-tetramethyl-piperidin-4-one

Refernces

• 1、 Ma, Yihan,Zhang, Xiaoyan,Cheng, Yinjia,Chen, Xiaosui,Li, Yong,Zhang, Aiqing. "Mussel-inspired preparation of C60 nanoparticles as photo-driven DNA cleavage reagents". . p. 18102 - 18108. Retrieved 2018.
• 2、 Iwamoto,Yoshioka,Yanagihara. "Singlet oxygen-producing activity and photodynamic biological effects of acridine compounds". . p. 2478 - 2483. Retrieved 1987.
• 3、 Nonogawa, Mitsuru,Arai, Toshiyuki,Endo, Nobuyuki,Pack, Seung Pil,Kodaki, Tsutomu,Makino, Keisuke. "Novel 6-formylpterin derivatives: Chemical synthesis and O2 to ROS conversion activities". . p. 1811 - 1816. Retrieved 2006.
• 4、 le Noble,W.J. et al.. "-". . p. 4710 - 4713. Retrieved 1971.
• 5、 Toda et al.. "". . p. 1904. Retrieved 1972.
• 6、 Xu, Fang,Li, Jin,Zhu, Ting-Ting,Yu, Sheng-Song,Zuo, Chong,Yao, Ri-Sheng,Qian, Hai-Sheng. "A new trick (hydroxyl radical generation) of an old vitamin (B2) for near-infrared-triggered photodynamic therapy". . p. 102647 - 102656. Retrieved 2016.
• 7、 -. "Method for preparing hindered amine nitroxide free radical compound by alkaline heterogeneous catalysis system". Paragraph 0046-0049; 0058-0059. . Retrieved 2021/09/26.
• 8、 -. "Preparation method for synthesizing polymerization inhibitor 702 from acetone and ammonia gas through one-pot method". Paragraph 0036; 0038-0050. . Retrieved 2021/04/28.