Production Method 1

504-20-1

826-36-8

Reaction Conditions

1.1 Reagents: Ammonia ,  Water

Reference

Evaluation of spin labeled tartaric and galactaric diamides as potential MRI contrast enhancing agents

Sosnovsky, Georges; et al, European Journal of Medicinal Chemistry, 1989, 24(3), 241-7

Production Method 2

2403-88-5

826-36-8

Reaction Conditions

1.1 Reagents: 3-Buten-2-one Catalysts: Palladate(2-), bis[μ-(acetato-κO:κO′)]tetrakis[(1,1-dimethylethyl)phenylphosphin… Solvents: Toluene ,  Water ;  16 h, 105 °C

Reference

Secondary Phosphine Oxides as Multitalented Preligands En Route to the Chemoselective Palladium-Catalyzed Oxidation of Alcohols

Vasseur, Alexandre; et al, ChemCatChem, 2017, 9(5), 728-732

Production Method 3

2403-88-5

826-36-8

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Isobutyraldehyde ,  (SP-4-2)-[2,18-Dimethyl 3,7,12,17-tetramethyl-21H,23H-porphine-2,18-dipropanoato… Solvents: Acetonitrile ;  60 min, 1 atm, 60 °C

Reference

Rapid aerobic oxidation of alcohols to carbonyl compounds with dioxygen using metallodeuteroporphyrin dimethyl esters as catalysts in the presence of isobutylaldehyde

Sun, Chengguo; et al, Heteroatom Chemistry, 2012, 23(3), 295-303

Production Method 4

36177-95-4

826-36-8

Reaction Conditions

1.1 Reagents: Acetyl chloride

Reference

Synthesis of 3-substituted derivatives of 2,2,6,6-tetramethylpiperidine: potential new spin labels

Rozantsev, E. G.; et al, Journal of Chemical Research, 1979, (8), 260-1

Production Method 5

556-72-9

826-36-8

Reaction Conditions

1.1 Reagents: Acetone Catalysts: Ammonium tetrafluoroborate ;  70 °C

Reference

Ammonium tetrafluoroborate

Friestad, Gregory K.; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-2

Production Method 6

556-72-9

826-36-8

Reaction Conditions

1.1 Catalysts: Acetone

Reference

A process for preparation of 2,2,6,6-tetramethyl-4-oxopiperidine

, Japan, , ,

Production Method 7

826-36-8

556-72-9

Reaction Conditions

1.1 Reagents: Ammonia Catalysts: Acetic acid (aluminum magnesium hydroxide complex)

Reference

Method for producing 2,2,6,6-tetramethyl-4-oxopiperidine and/or 2,2,4,4,6-pentamethyl-2,3,4,5-tetrahydropyrimidine

, Japan, , ,

Production Method 8

504-20-1

826-36-8

Reaction Conditions

1.1 Reagents: Ammonia Solvents: Water ;  48 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt
1.3 Reagents: Potassium hydroxide Solvents: Water ;  basified, rt

Reference

Synthesis of triacetonamine N-alkyl derivatives reinvestigated

Banert, Klaus; et al, ARKIVOC (Gainesville, 2012, (3), 379-390

Production Method 9

625-04-7

826-36-8

Reaction Conditions

1.1 Reagents: Calcium chloride ;  rt → 59 °C; 5 d, 59 °C

Reference

Synthesis of Novel Hindered Amine Light Stabilizers (HALS) and Their Copolymerization with Ethylene or Propylene over Both Soluble and Supported Metallocene Catalyst Systems

Wilen, Carl-Eric; et al, Macromolecules, 2000, 33(14), 5011-5026

Production Method 10

826-36-8

Reaction Conditions

1.1 Reagents: Ammonia ,  Calcium chloride ;  4 d, -47 °C; -47 °C → 59 °C; 4 d, 59 °C

Reference

Synthesis of Novel Hindered Amine Light Stabilizers (HALS) and Their Copolymerization with Ethylene or Propylene over Both Soluble and Supported Metallocene Catalyst Systems

Wilen, Carl-Eric; et al, Macromolecules, 2000, 33(14), 5011-5026

Production Method 11

556-72-9

826-36-8

22280-51-9

35814-33-6

Reaction Conditions

1.1 Reagents: Ammonium chloride

Reference

Oxoammonium salts. 5. A new synthesis of hindered piperidines leading to unsymmetrical TEMPO-type nitroxides. Synthesis and enantioselective oxidations with chiral nitroxides and chiral oxoammonium salts

Ma, Zhenkun; et al, Journal of Organic Chemistry, 1993, 58(18), 4837-43

Production Method 12

504-20-1

826-36-8

Reaction Conditions

1.1 Reagents: Ammonia Solvents: Water ;  -80 °C → 85 °C

Reference

The Synthesis Of EPR Differentiable Spin-labels And Their Coupling To Uridine

Frolow, Olga; et al, Nucleosides, 2007, 26(6-7), 655-659

Production Method 13

826-36-8

Reaction Conditions

1.1 Reagents: Ammonia Catalysts: Iron acetate
1.2 Catalysts: Iron acetate

Reference

Preparation of 2,2,6,6-tetramethyl-4-oxopiperidine (triacetonamine)

, Japan, , ,

Production Method 14

5554-54-1

826-36-8

Reaction Conditions

1.1 Solvents: Acetone ,  Water
1.2 Reagents: Sulfuric acid ,  Potassium sulfate
1.3 Reagents: Sodium hydroxide

Reference

Crowded piperidines with intramolecularly hydrogen-bonded nitrogen: synthesis and conformation study

Belostotskii, Anatoly M.; et al, Chemistry - A European Journal, 2002, 8(13), 3016-3026

Production Method 15

208348-34-9

826-36-8

Reaction Conditions

1.1 Reagents: Oxygen ;  1 atm, 298 K

Reference

Solvent free mechanochemical oxygenation of fullerene under oxygen atmosphere

Watanabe, Hiroto; et al, Tetrahedron Letters, 2007, 48(46), 8132-8137

Production Method 16

38697-07-3

826-36-8

Reaction Conditions

1.1 Catalysts: Ethylenediamine ;  24 h, rt

Reference

Two-step synthesis and biological evaluation of calyxamines A and B

Meza-Leon, Rosa-L.; et al, Tetrahedron Letters, 2013, 54(50), 6852-6854

Production Method 17

556-72-9

826-36-8

Reaction Conditions

1.1 Catalysts: Ammonium tetrafluoroborate

Reference

Manufacture of 2,2,6,6-tetramethylpiperidin-4-one

, Japan, , ,

Production Method 18

556-72-9

826-36-8

Reaction Conditions

1.1 Catalysts: Ferric acetate

Reference

Preparation of 2,2,6,6-tetramethyl-4-oxopiperidine

, Japan, , ,

Production Method 19

826-36-8

Reaction Conditions

1.1 Reagents: Oxygen ;  1 h, 1 atm, 298 K
2.1 Reagents: Oxygen ;  1 atm, 298 K

Reference

Solvent free mechanochemical oxygenation of fullerene under oxygen atmosphere

Watanabe, Hiroto; et al, Tetrahedron Letters, 2007, 48(46), 8132-8137

Production Method 20

826-36-8

70-16-6

Reaction Conditions

1.1 Reagents: Thiophenol ,  Hydrochloric acid Solvents: Methanol ,  Water

Reference

Stable free radicals. III. Reactions of stable nitroxide radicals with S-radicals derived from benzenethiols and thiamine

Murayama, Keisuke; et al, Bulletin of the Chemical Society of Japan, 1969, 42(7), 1942-7

Triacetonamine Raw materials

• 2,2,6,6-tetramethylpiperidin-4-ol
• 1,2,2,6,6-Pentamethyl-4-piperidone
• Morpholine, 4-(1,2,3,6-tetrahydro-2,2,6,6-tetramethyl-4-pyridinyl)-
• 2,6-dimethylhepta-2,5-dien-4-one
• Pyrimidine,1,2,5,6-tetrahydro-2,2,4,6,6-pentamethyl-
• propan-2-imine
• 4-Amino-4-methyl-2-pentanone

Triacetonamine Preparation Products

• 1-Azaspiro[5.5]undecan-4-one, 2,2-dimethyl- (22280-51-9)
• Triacetonamine (826-36-8)
• Pyrimidine,1,2,5,6-tetrahydro-2,2,4,6,6-pentamethyl- (556-72-9)
• Thiamine ion (70-16-6)
• 7-Azadispiro[5.1.5.3]hexadecan-15-one (35814-33-6)

• 1. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409
• 2. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739
• 3. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
  Erika A. Cobar,Paul R. Horn,Robert G. Bergman,Martin Head-Gordon Phys. Chem. Chem. Phys., 2012,14, 15328-15339
• 4. Evolution study of photo-synthesized gold nanoparticles by spectral deconvolution model: a quantitative approach
  Chung-Sung Yang,Mong-Shian Shih,Fang-Yi Chang New J. Chem., 2006,30, 729-735
• 5. Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors
  Tengfei Yu,Yuehan Wu,Wei Li,Bin Li RSC Adv., 2014,4, 34134-34143

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Piperidines Piperidinones
• Solvents and Organic Chemicals Organic Compounds Aldehyde/Ketone

Triacetonamine (CAS No. 826-36-8): A Comprehensive Overview of Its Applications and Recent Research Developments

Triacetonamine, with the chemical formula C?H??NO, is a significant compound in the field of organic chemistry and pharmaceutical research. Its CAS number, 826-36-8, uniquely identifies it in scientific literature and industrial applications. This compound has garnered considerable attention due to its versatile reactivity and its role as a precursor in the synthesis of various pharmacologically active molecules.

The structural framework of Triacetonamine consists of an acetyl group attached to a secondary amine, making it a valuable intermediate in the formation of more complex molecules. This unique structure allows it to participate in a wide range of chemical reactions, including nucleophilic additions, condensations, and reductions, which are pivotal in drug development.

In recent years, Triacetonamine has been extensively studied for its potential applications in medicinal chemistry. One of the most notable areas of research involves its use as a building block in the synthesis of antibiotics and antiviral agents. The compound's ability to undergo facile functionalization makes it an attractive candidate for modifying existing drug molecules or creating novel therapeutic agents.

A particularly intriguing aspect of Triacetonamine is its role in the development of protease inhibitors. Proteases are enzymes that play crucial roles in various biological processes, including virus replication and inflammation. By inhibiting specific proteases, Triacetonamine-derived compounds have shown promise in treating conditions such as HIV/AIDS and certain types of cancer. Recent studies have highlighted its efficacy in targeting viral proteases, thereby preventing the maturation of viral particles and reducing viral load in infected individuals.

Moreover, Triacetonamine has found applications in the field of materials science. Its derivatives exhibit interesting properties that make them suitable for use as catalysts and ligands in organic synthesis. For instance, certain complexes formed with transition metals have demonstrated enhanced catalytic activity in cross-coupling reactions, which are fundamental to constructing complex organic molecules.

The pharmaceutical industry has also explored the use of Triacetonamine in the development of central nervous system (CNS) drugs. Its structural motif is reminiscent of several neuroactive compounds, suggesting potential interactions with neurotransmitter receptors. Preliminary research indicates that derivatives of Triacetonamine may modulate the activity of serotonin and dopamine receptors, offering a possible avenue for treating neurological disorders such as depression and Parkinson's disease.

In conclusion, the multifaceted applications of Triacetonamine underscore its importance as a versatile intermediate in chemical synthesis. Its role in pharmaceutical research, particularly in the development of antibiotics, antivirals, and CNS drugs, highlights its significance in addressing global health challenges. As research continues to uncover new methodologies for functionalizing this compound, its potential applications are expected to expand further, solidifying its place as a cornerstone molecule in modern chemistry and medicine.

• 54156-50-2(9-Azabicyclo[3.3.1]nonan-3-one, 1,5,7-trimethyl-)
• 10581-38-1(2,2,6,6-Tetramethyl-4-piperidone monohydrate)
• 33973-59-0(2,2,6,6-Tetramethylpiperidin-4-one hydrochloride)
• 15486-23-4(9-Azabicyclo[3.3.1]nonan-3-one,1-methyl-, (1S,5R)-)
• 362053-34-7(6-azaspiro4.5decan-9-one)
• 52168-48-6(4-Oxo-2,2,6,6-tetramethylpiperidine-d17)
• 686778-07-4( )
• 77515-68-5(1-Azaspiro[5.5]undecan-8-one)
• 80404-11-1(4-oxo-2,2,6,6-tetramethylpiperidine (d17, 15n))
• 133568-79-3(2-Ethyl-2,6,6-trimethylpiperidin-4-one)