2,2,6,6-Tetramethylpiperidine

Base Information

• Chemical Name: 2,2,6,6-Tetramethylpiperidine
• CAS No.: 768-66-1
• Molecular Formula: C9H19N
• Molecular Weight: 141.257
• Hs Code.: 29333999
• European Community (EC) Number: 212-199-3
• NSC Number: 102838
• UNII: 44N9S1YCFM
• DSSTox Substance ID: DTXSID0061113
• Nikkaji Number: J1.732I
• Wikipedia: 2,2,6,6-Tetramethylpiperidine
• Wikidata: Q4596748
• ChEMBL ID: CHEMBL2448812
• Mol file: 768-66-1.mol

Synonyms:2,2,6,6-tetramethylpiperidide;2,2,6,6-tetramethylpiperidine

Chemical Property of 2,2,6,6-Tetramethylpiperidine

Chemical Property:

• Appearance/Colour: clear colorless to light yellow-green liquid
• Vapor Pressure: 2.73mmHg at 25°C
• Melting Point: -59 °C
• Refractive Index: n20/D 1.445(lit.)
• Boiling Point: 157.6 °C at 760 mmHg
• PKA: 11.07(at 25℃)
• Flash Point: 24.4 °C
• PSA: 12.03000
• Density: 0.787 g/cm³
• LogP: 2.64590
• Storage Temp.: Flammables area
• Sensitive.: Air Sensitive
• Solubility.: MISCIBLE
• Water Solubility.: MISCIBLE
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 141.151749610
• Heavy Atom Count: 10
• Complexity: 111

Purity/Quality:

99% ^*data from raw suppliers

2,2,6,6-Tetramethylpiperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, F, C
• Hazard Codes: Xn,F,C
• Statements: 10-22-36/37/38
• Safety Statements: 26-37/39-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Cyclic
• Canonical SMILES: CC1(CCCC(N1)(C)C)C
• Uses: 2,2,6,6-Tetramethylpiperidine is used in the syntheses of HMP-Y1, Hibarimicinone and HMP-P1, tyrosine kinase inhibitors. 2,2,6,6-Tetramethylpiperidine is a hindered base used to prepare metallo-amide bases and selective generation of silylketene acetals. It is used in the preparation of hibarimicinone, (Z)-silylketene acetal and 4-substituted quinazoline. It acts as a precursor to Lithium tetramethylpiperidide and (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl radical. The lithium amide has been used to efficiently ortho deprotonate pyridine-3-carboxamides.

Technology Process of 2,2,6,6-Tetramethylpiperidine

There total 96 articles about 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: 100.0%

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 2,2,6,6-tetramethyl-piperidine (768-66-1)

Guidance literature:

With hydrogenchloride; hydrogen; platinum(IV) oxide; for 40h; under 1.5 Torr;

Reference yield: 89.6%

triacetone-amine hydrate + platinum (IV) oxide monohydrate + N-methyl-2,2,6,6-tetramethylpiperidone → 2,2,6,6-tetramethyl-piperidine (768-66-1)

Guidance literature:

In sulfuric acid; water;

Reference yield: 80.0%

2,3-bis(trimethylsilyl)-1,3-butadiene-1,4-dione (145178-53-6) → 2,2,6,6-tetramethyl-piperidine (768-66-1) + 1-benzyloxy-2,2,6,6-tetramethylpiperidine (102261-92-7) + bis(trimethylsilyl) maleic anhydride

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; In toluene; at 90 ℃; for 3h;

DOI:10.1021/ja982944i

upstream raw materials:

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

1,2,2,6,6-pentamethylpiperidine

9,10-phenanthrenequinone

2,2,6,6-tetramethyl-1-nitrosopiperidine

Downstream raw materials:

1,2,2,6,6-pentamethylpiperidine

phenyl(2,2,6,6-tetramethylpiperidin-1-yl)methanone

1-Ethyl-2,2,6,6-tetramethylpiperidine

2,2,6,6-tetramethylpiperidine-1-carbonyl chloride

Refernces

• 1、 Zhang, Ling,Zhu, Jie,Ma, Jing,Wu, Lei,Zhang, Wei-Hua. "Visible-Light-Driven α-Allenylic C-O Bond Cleavage and Alkenyl C-S Formation: Metal-Free and Oxidant-Free Thiolation of Allenyl Phosphine Oxides". . p. 6308 - 6311. Retrieved 2017.
• 2、 Kaplan, Ruth W.,Turnbull, Mark M.. "2,2,6,6-tetramethylpiperidinium chloride". . p. 2049 - 2051. Retrieved 1996.
• 3、 Xu, Jincheng,Ding, Aishun,Zhang, Yanbin,Guo, Hao. "Photochemical Synthesis of 1,4-Dicarbonyl Bifluorene Compounds via Oxidative Radical Coupling Using TEMPO as the Oxygen Atom Donor". . p. 3656 - 3666. Retrieved 2021.
• 4、 K?nig, Burkhard,Wang, Hua,Wang, Shun. "Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation". supporting information. p. 1653 - 1665. Retrieved 2021/06/17.
• 5、 Zhang, Xiao-Wei,Jiang, Guo-Qing,Lei, Shu-Hui,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao. "Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds". supporting information. p. 1611 - 1615. Retrieved 2021/03/03.