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:

99.9% ^*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

Synthetic studies on N-alkoxyamines: A mild and broadly applicable route starting from nitroxide radicals and aldehydes

10.1021/jo802403j

The research explores a novel method for synthesizing a variety of 2,2,6,6-tetramethylpiperidine-based N-alkoxyamines using a copper-catalyzed fragmentation reaction of aldehyde peroxides in the presence of TEMPO or its derivatives. The purpose of this study is to develop a simple, selective, scalable, and cost-efficient route for producing N-alkoxyamines, which have applications in controlled radical polymerizations, polymer light stabilization, and as fireproofing agents. The study concludes that this method is mild, broadly applicable, and tolerates a wide range of functional groups. It allows reactions to be performed in wet solvents and under aerobic conditions, simplifying operations. The process generates minimal byproducts and requires only small excesses of aldehyde and hydrogen peroxide, making it suitable for industrial-scale applications. The findings suggest that this method could open new opportunities in living radicalization polymer and natural product synthesis, potentially reducing the need for certain protecting groups.