79-55-0

Usage

Uses

1. Pharmaceutical Industry:
1,2,2,6,6-Pentamethylpiperidine is used as a ganglionic blocker and antihypertensive agent for the treatment of high blood pressure. It functions by blocking the transmission of nerve impulses in the autonomic nervous system, leading to a reduction in blood pressure.
2. Chemical Synthesis:
In the field of chemical synthesis, 1,2,2,6,6-Pentamethylpiperidine is used in the synthesis of BN-fused polycyclic aromatic molecules, which have potential applications in electronic materials and apparatus. Its unique structure allows for the formation of stable and functionalized compounds with desirable electronic properties.
3. Catalyst in Organic Chemistry:
1,2,2,6,6-Pentamethylpiperidine also serves as a catalyst for the chemoselective silylation of benzylic alcohols. This selective reaction is crucial in the synthesis of various organic compounds, as it allows for the formation of specific products without the need for protection or deprotection steps.
4. Pharmacological Research:
1,2,2,6,6-Pentamethylpiperidine has been evaluated for its pharmacological properties, particularly in the antagonism of nicotine's central effects. In studies, it was found to increase the ED50 of nicotine, demonstrating its potential as a therapeutic agent for nicotine addiction and related disorders.
5. Fluorescent Materials:
In the development of fluorescent materials, 1,2,2,6,6-Pentamethylpiperidine is used to modify the focal 1,8-naphthalimide fluorophores in the antennae. This modification improves the photostability of the fluorophores, making them suitable for applications in sensing, imaging, and other areas where stable fluorescence is required.

InChI:InChI=1/C10H21N/c1-9(2)7-6-8-10(3,4)11(9)5/h6-8H2,1-5H3/p+1

Upstream product

• 54262-97-4 2,2,6,6-tetramethylpiperidine-1-carboxaldehyde 
• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 80-48-8 methyl p-toluene sulfonate 
• 2564-83-2 2,2,6,6-tetramethyl-piperidine-N-oxyl 
• 75-05-8 acetonitrile 
• 124-38-9 carbon dioxide 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 
• 67-68-5 dimethyl sulfoxide 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 1402724-32-6 2,2,6,6-tetramethyl-1-methylenepiperidinium tetrakis(pentafluorophenyl)borate 
• 771436-36-3 C₁₀H₂₁NO 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 

Downstream Products

• 768-66-1 2,2,6,6-tetramethyl-piperidine 
• 137124-55-1 9-hydroxy-9-(hydroxymethyl)anthrone 
• 5132-07-0 TEMPO 
• 54262-97-4 2,2,6,6-tetramethylpiperidine-1-carboxaldehyde 
• 33815-55-3 (2R,3R)-2-methyl-3-phenyl-2,3-dihydro-1H-inden-1-one 
• 960505-96-8 (2S,3S)-2-methyl-3-phenylindanone 
• 52957-74-1 2-methyl-3-phenyl-1-indanone 
• 13304-52-4 2-methyl-3-phenylinden-1-one 

Relevant academic research and scientific papers

Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO2for consecutiveN-methylation of amines

A mesoionic N-heterocyclic olefin (mNHO) was introduced as a metal-free catalyst for the reductive functionalization of CO2leading to consecutive doubleN-methylation of primary amines in the presence of 9-borabicyclo[3.3.1]nonane (9-BBN). A wide range of secondary amines and primary amines were successfully methylated under mild conditions. The catalyst sustained over six successive cycles ofN-methylation of secondary amines without compromising its activity, which encouraged us to check its efficacy towards doubleN-methylation of primary amines. Moreover, this method was utilized for the synthesis of two commercially available drug molecules. A detailed mechanistic cycle was proposed by performing a series of control reactions along with the successful characterisation of active catalytic intermediates either by single-crystal X-ray study or by NMR spectroscopic studies in association with DFT calculations.

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2

We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.

Catalyst-free selective: N -formylation and N -methylation of amines using CO2 as a sustainable C1 source

We herein describe catalyst-free selective N-formylation and N-methylation of amines using CO2 as a sustainable C1 source. By tuning the reaction solvent and temperature, the selective synthesis of formamides and methylamines is achieved in good to excellent yields using sodium borohydride (NaBH4) as a sustainable reductant.

UiO-type metal-organic frameworks with NHC or metal-NHC functionalities for: N-methylation using CO2 as the carbon source

We demonstrate the first metal-organic framework (MOF) that catalyzes N-methylation of amines using 1 atm CO2 and phenylsilane under ambient conditions. Compared with its homogeneous analog, the incorporation of N-heterocyclic carbene (NHC) into the MOF provides more efficient catalysis with improved reaction kinetics, turnover numbers and recyclability. Moreover, the metalated NHC functionalized MOF achieves direct N-methylation of amines bearing carboxylate moieties, which are common building blocks in pharmaceutical chemistry.

Selective formylation or methylation of amines using carbon dioxide catalysed by a rhodium perimidine-based NHC complex

Carbon dioxide can play a vital role as a sustainable feedstock for chemical synthesis. To be viable, the employed protocol should be as mild as possible. Herein we report a methodology to incorporate CO2 into primary, secondary, aromatic or alkyl amines catalysed by a Rh(i) complex bearing a perimidine-based NHC/phosphine pincer ligand. The periminide-based ligand belongs to a class of 6-membered NHC ligand accessed through chelate-assisted double C-H activation. N-Formylation and -methylation of amines were performed using a balloon of CO2, and phenylsilane as the reducing agent. Product selectivity between formylated and methylated products was tuned by changing the solvent, reaction temperature and the quantity of phenylsilane used. Medium to excellent conversions, as well as tolerance to a range of functional groups, were achieved. Stoichiometric reactions with reactants employed in catalysis and time course studies suggested that formylation and methylation reactions of interest begin with hydrosilylation of CO2 followed by reaction with amine substrates.

Diverse catalytic reactivity of a dearomatized PN3P?-nickel hydride pincer complex towards CO2 reduction

A dearomatized PN3P?-nickel hydride complex has been prepared using an oxidative addition process. The first nickel-catalyzed hydrosilylation of CO2 to methanol has been achieved, with unprecedented turnover numbers. Selective methylation and formylation of amines with CO2 were demonstrated by such a PN3P?-nickel hydride complex, highlighting its versatile functions in CO2 reduction.

Use for Boron Formates for Reducing Unsaturated Organic Functions

The present invention relates to a method for reducing unsaturated organic compounds chosen from the group formed by the aldehydes, the ketones, the imines, the carboxylic acids, the amides, and the esters with a boron formate having the formula (I) in the presence of a solvent and optionally a base. The invention also relates to the use of the method for reducing unsaturated organic compounds chosen from the group formed by the aldehydes, the ketones, the imines, the carboxylic acids, the amides, and the esters according to the invention in the preparation of methanol, methylated amines, formaldehyde and alcohols; for the preparation of reactants for Suzuki coupling reactions; and in the manufacturing of vitamins, pharmaceutical products, glues, acrylic fibres, synthetic leather, pesticides.

Catalyst-free N-methylation of amines using CO2

Recently, utilizing CO2 as a methylation reagent to construct functional chemicals has attracted significant attention. However, the conversion of CO2 is still a challenge due to its inherent inertness. In this study, we have developed a catalyst-free N-methylation of amines to prepare numerous methylamines using CO2 as a methyl source. By utilizing 2 eq. PhSiH3 as the reductant, amines could undergo N-methylation under 1 atm of CO2 in DMF at 90 °C. Aliphatic and aromatic amines were compatible, generating the desired products in up to 95% yield.

Metal-free disproportionation of formic acid mediated by organoboranes

In the presence of dialkylboranes, formic acid can be converted to formaldehyde and methanol derivatives without the need for an external reductant. This reactivity, in which formates serve as the sole carbon and hydride sources, represents the first exam

One-pot three-component synthesis of quinazolines: Via a copper-catalysed oxidative amination reaction

A copper-catalysed three-component reaction for constructing a series of quinazoline derivatives has been developed. In this system, solvents act as the reactants and different functional groups are well tolerated to obtain corresponding products in moderate to good yields.