1-Hydroxy-2,2,6,6-tetramethylpiperidine

Base Information

• Chemical Name: 1-Hydroxy-2,2,6,6-tetramethylpiperidine
• CAS No.: 7031-93-8
• Molecular Formula: C9H19NO
• Molecular Weight: 157.256
• Mol file: 7031-93-8.mol

Synonyms:2,2,6,6-tetramethylpiperidine-N-hydroxide;1-hydroxy-2,2,6,6-tetramethyl-1-piperidinyloxy;2,2,6,6-tetramethyl-piperidinol;

Chemical Property of 1-Hydroxy-2,2,6,6-tetramethylpiperidine

Chemical Property:

• Melting Point: 39-40 °C
• Boiling Point: 208.8±7.0 °C(Predicted)
• PKA: 14.28±0.60(Predicted)
• PSA: 23.47000
• Density: 0.917±0.06 g/cm3(Predicted)
• LogP: 2.35660
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

2,2,6,6-Tetramethyl-1-hydroxypiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2,2,6,6-Tetramethyl-1-hydroxypiperidine is a reactant used in various synthesis and investigations. It was used as a reactant in the study of predicting organic hydrogen atom transfer rate constants using the Marcus cross relation. 2,2,6,6-Tetramethyl-1-hydroxypiperidine was also used as a reactant in the preparation of ammonia from an iron nitrido complex.

Technology Process of 1-Hydroxy-2,2,6,6-tetramethylpiperidine

There total 88 articles about 1-Hydroxy-2,2,6,6-tetramethylpiperidine 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: 98.0%

thiophene-2-carbaldehyde (98-03-3) + 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) → 2,2,6,6-tetramethylpiperidin-1-ol (7031-93-8) + thiophene-2-carboxylic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester (1100308-41-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1,2,4-triazolium iodide; In tetrahydrofuran; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1002/anie.200802735

Reference yield: 98.0%

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) + m-Chlorobenzaldehyde (587-04-2) → 2,2,6,6-tetramethylpiperidin-1-ol (7031-93-8) + 3-chloro-benzoic acid 2,2,6,6-tetramethyl-piperidin-1-yl ester (1100308-37-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-dimethyl-1,2,4-triazolium iodide; In tetrahydrofuran; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1002/anie.200802735

Reference yield: 96.0%

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) → 2,2,6,6-tetramethylpiperidin-1-ol (7031-93-8)

Guidance literature:

With sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; In water; at 20 ℃;

DOI:10.1002/chem.201501823

upstream raw materials:

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

2,2,6,6-tetramethylpiperidin-1-oxoammonium chloride

3-phenyl-1-(2′,2′,6′,6′-tetramethyl-1′-piperidinyloxy)-propane

N,N-dimethyl-aniline

Downstream raw materials:

2-(2-methyl-2-nitropropyl) 3-nitroimidazo<1,2-a>pyrimidine

2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphine ruthenium(II) carbonyl

Ru(ONC₅H₆(CH₃)4)(N₄C₂₀H₄(C₂H₅)8)(CO)

[Ru(II)(1,1,1-5,5,5-hexafluoro-2,4-pentanedionato)2(2-(2'-pyridyl)imidazole)]

Refernces

• 1、 Bordwell, Frederick G.,Liu, Wei-Zhong. "Solvent effects on homolytic bond dissociation energies of hydroxylic acids". . p. 10819 - 10823. Retrieved 1996.
• 2、 Huang, Min-Hua,Hong, Yu,Hu, Jian-Qiang,Yang, Shi-Zhao,Zhu, Yi-Long,Wang, De-Cai,Jiang, Bo. "Iron(III)-promoted hydrofunctionalization/bicyclization of 1,7-enynes toward benzo[a]fluoren-5-ones". . . Retrieved 2020.
• 3、 Ishizaka, Yusuke,Jheng, Nai-Yuan,Naganawa, Yuki,Nakajima, Yumiko,Sekiguchi, Akira. "Co(i) complexes with a tetradentate phenanthroline-based PNNP ligand as a potent new metal-ligand cooperation platform". . p. 14592 - 14597. Retrieved 2020.
• 4、 Baschieri, Andrea,Valgimigli, Luca,Gabbanini, Simone,Dilabio, Gino A.,Romero-Montalvo, Eduardo,Amorati, Riccardo. "Extremely Fast Hydrogen Atom Transfer between Nitroxides and HOO · Radicals and Implication for Catalytic Coantioxidant Systems". . p. 10354 - 10362. Retrieved 2018.
• 5、 Kadassery, Karthika J.,Sethi, Komal,Fanara, Paul M.,Lacy, David C.. "CO-Photolysis-Induced H-Atom Transfer from MnIO-H Bonds". . p. 4679 - 4685. Retrieved 2019.
• 6、 Uyeda, Christopher,Peters, Jonas C.. "Access to formally Ni(i) states in a heterobimetallic NiZn system". . p. 157 - 163. Retrieved 2013.
• 7、 Saouma, Caroline T.,Morris, Wesley D.,Darcy, Julia W.,Mayer, James M.. "Protonation and proton-coupled electron transfer at S-ligated [4Fe-4S] clusters". . p. 9256 - 9260. Retrieved 2015.
• 8、 Sun, Jinwei,Zhang, Yu,Mathan, Sankaran,Wang, Yi,Pan, Yi. "Metal-Free Tandem Oxidative Coupling of Primary Alcohols with Azoles for the Synthesis of Hemiaminal Ethers". . p. 3380 - 3385. Retrieved 2016.
• 9、 Dahiya, Anjali,Das, Bubul,Sahoo, Ashish Kumar,Patel, Bhisma K.. "Visible-Light-Driven Isocyanide Insertion to o-Alkenylanilines: A Route to Isoindolinone Synthesis". supporting information. p. 966 - 973. Retrieved 2022/02/07.