2403-89-6

Basic information

• Product Name: 1,2,2,6,6-Pentamethyl-4-piperidinol
• Synonyms: 1,2,2,6,6-pentamethyl-4-piperidino;1,2,2,6,6-PENTAMETHYL-4-PIPERIDINOL;1,2,2,6,6-Pentamethylpiperidin-4-ol;1,2,2,6,6-PENTAMETHYL-4-HYDROXYPIPERIDINE;4-HYDROXY-1,2,2,6,6-PENTAMETHYLPIPERIDINE;METHYL-TAA-OL;N-METHYL-2,2,6,6-TETRAMETHYL-4-PIPERIDINOL;N-METHYL-TRIACETONAMINO ALCOHOL
• CAS NO: 2403-89-6
• Molecular Formula: C₁₀H₂₁NO
• Molecular Weight: 171.28
• EINECS: 219-292-8
• Product Categories: Industrial/Fine Chemicals;API intermediates;Building Blocks;C10;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines
• Mol File: 2403-89-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: 72-76 °C
• Boiling Point: 238 °C
• Flash Point: 118 °C
• Appearance: Light yellow/Flakes
• Density: 0.967
• Vapor Pressure: 0.0129mmHg at 25°C
• Refractive Index: 1.4621 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.93±0.60(Predicted)
• Water Solubility: 4.8 g/100 mL (20 ºc)
• BRN: 1498
• CAS DataBase Reference: 1,2,2,6,6-Pentamethyl-4-piperidinol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,2,6,6-Pentamethyl-4-piperidinol(2403-89-6)
• EPA Substance Registry System: 1,2,2,6,6-Pentamethyl-4-piperidinol(2403-89-6)

Safety Data

• Hazard Codes: Xi,C,N,Xn
• Statements: 43-34-22-51/53
• Safety Statements: 36/37-45-36/37/39-26-61
• RIDADR: UN3261 - class 8 - PG 1 - EHS - Corrosive solid, acidic, organic
• WGK Germany: 2
• Hazardous Substances Data: 2403-89-6(Hazardous Substances Data)

Usage

Description

1,2,2,6,6-Pentamethyl-4-piperidinol is a light yellow flake chemical compound with a unique molecular structure that features five methyl groups and a hydroxyl group attached to a piperidine ring. It is known for its versatile applications in various chemical and pharmaceutical industries.

Uses

Used in Chemical Synthesis:
1,2,2,6,6-Pentamethyl-4-piperidinol is used as a reactant for the synthesis of various compounds, including:
1. Photostable blue emitting naphthalimides, which are important for the development of advanced materials with potential applications in optoelectronics and imaging technologies.
2. Blue fluorescent naphthalimide pH chemosensors, which can be utilized in the detection and monitoring of pH levels in different environments.
3. Crowded piperidines with intramolecularly hydrogen-bonded nitrogen, which are valuable for studying the effects of molecular crowding on chemical reactions and biological systems.
4. Spiropyrans and spirooxazines, which are photochromic compounds that can undergo reversible color changes upon exposure to light, finding applications in molecular switches and optical data storage.
5. Amine photoredox reactions, which are essential for the development of new synthetic methods and the preparation of complex organic molecules.
Used in Pharmaceutical Industry:
1,2,2,6,6-Pentamethyl-4-piperidinol is used as a reactant for the synthesis of PDGFR kinase inhibitors, which are important in the treatment of various diseases, including cancer and fibrosis. These inhibitors can help regulate cell signaling pathways and prevent uncontrolled cell growth.
Used in Polymer Industry:
1,2,2,6,6-Pentamethyl-4-piperidinol can be applied to the preparation of a new diol-functionalized amine light stabilizer, which is crucial for the development of polymer materials with enhanced stability and resistance to degradation caused by exposure to light and oxygen. This application is particularly relevant in the plastics, coatings, and elastomers industries, where the need for durable and long-lasting materials is essential.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H21NO/c1-9(2)6-8(12)7-10(3,4)11(9)5/h8,12H,6-7H2,1-5H3/p+1

Upstream product

• 2403-88-5 4-hydroxy-2,2,6,6-tetramethylpiperidine 
• 50-00-0 formaldehyd 
• 74-88-4 methyl iodide 
• 138847-19-5 C₄₄H₅₆O₄*C₁₀H₂₁NO 
• 124-38-9 carbon dioxide 
• 62421-70-9 C₁₀H₂₁NO₂ 

Downstream Products

• 2403-88-5 4-hydroxy-2,2,6,6-tetramethylpiperidine 
• 85111-09-7 1-(2-Hydroxy-2,3-diphenylpropyl)2,2,6,6-tetramethyl-4-piperidol 
• 80784-66-3 4,4'-Dihydroxy-2,2,2',2',6,6,6',6'-octamethyl-1,1'-ethylenebispiperidine 
• 464-72-2 tetraphenylethane-1,2-diol 
• 80784-67-4 1-(2-Hydroxy-2,2-diphenylethylethyl)-2,2,6,6-tetramethyl-4-piperidol 
• 85111-08-6 1-(9-Hydroxy-9-xanthenyl)methyl-2,2,6,6-tetramethyl-4-piperidol 
• 85111-10-0 1-(2-Hydroxy-2,4-diphenylbutyl)-2,2,6,6-tetramethyl-4-piperidol 
• 137124-55-1 9-hydroxy-9-(hydroxymethyl)anthrone 
• 1636-34-6 2,3-diphenyl-2,3-butanediol 
• 80784-68-5 1-(2-Hydroxy-2-phenylpropyl)-2,2,6,6-tetramethyl-4-piperidol 
• 85111-11-1 1-(2-Hydroxy-2-methylpropyl)-2,2,6,6-tetramethyl-4-piperidol 
• 3225-30-7 hydroquinone radical 
• 468103-26-6 1,2,2,6,6-pentamethylpiperidin-4-yl 3-(5-chlorobenzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate 
• 1027092-45-0 1,2,2,6,6-pentamethylpiperidin-4-yl 3-(5-phenylsulfonylbenzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate 

Relevant articles and documents

A sterically controlled recyclable system: Reversible photoredox reactions between anthraquinone and hindered tertiary amines

Photochemical reactions of 9,10-anthraquinone (AQ) with sterically hindered tertiary amines have been studied. The reactivity and products are strongly dependent on the structure of the tertiary amine. Irradiation of AQ in the presence of the sterically hindered amine 1,2,2,6,6-pentamethyl-4-piperidinol (3) (or 1,2,2,6,6-pentamethylpiperidine (5)) in degassed dry benzene leads chiefly to the formation of 9-hydroxy-9-[N-(2,2,6,6-tetramethyl-4-piperidinol)-methyl]anthrone (8), which is found to be metastable at room temperature under vacuum. The reaction may be thermally reversed to regenerate the starting materials. The photolysis products and thermal reversion are solvent dependent. While in dry benzene adduct 8 is the major product, in dry acetonitrile the ionic redox products AQH-and iminium cation are detected and no thermal reversal occurs. The results are explained in terms of equilibrium between a product ion pair (AQH-, iminium+) and a metastable adduct 8. In the presence of water, the reaction leads to the formation of a stable product, 9-hydroxy-9-(hydroxymethyl)anthrone (6). Different reactivity is observed upon irradiation of AQ in the presence of the sterically less hindered tertiary amine trans-tropine (1).

Synthetic method of light stabilizer intermediate of 1,2,2,6,6-pentamethyl-4-pipradrol

The invention provides a synthetic method of a light stabilizer intermediate of 1,2,2,6,6-pentamethyl-4-pipradrol, and particularly relates to the technical field of light stabilizer preparation. Themethod comprises two step reactions; in the first step, 2,2,6,6-tetramethyl-4-pipradrol and paraformaldehyde are mixed according to a certain proportion and are added into a solvent; stirring is performed for a certain time at the ordinary pressure and a certain reaction temperature, so that the 2,2,6,6-tetramethyl-4-pipradrol completely reacts; then, cooling is performed to reach room temperature; filtering is performed to remove excessive paraformaldehyde; a hydroxymethylated product is obtained; in the second step, a reduction type solid catalyst is charged into a fixed bed reactor; the solvent is added into the reaction liquid; the mixture is continuously introduced into the fixed bed reactor at a certain feeding speed; hydrogen gas is introduced; heating is performed; the reaction liquid continuously flows out from the lower end of the fixed bed reactor; flowing-out reaction liquid is subjected to cooling, gas-liquid separation, liquid filtering, filter liquid solvent steaming removal and purification; the target product is obtained. The synthetic method has the advantages that the preparation is simple and convenient; economic performance and environment-friendly effects areachieved; the product quality is high; the yield is high; the method is suitable for industrial production.

N-Methylation of amine and nitro compounds with CO2/H2 catalyzed by Pd/CuZrOx under mild reaction conditions

An active Pd/ZrCuOx catalyst was prepared for the reductive amination of CO2. The N-methylation of amines and nitro compounds with CO2/H2 can be realized with up to 97% yield under relatively mild reaction condi