19971-12-1

Usage

Uses

Used in Pharmaceutical Industry:
3,5-dibromo-2,2,6,6-tetramethyl-4-piperidone hydrobromide is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its chemical properties allow it to be a key component in the synthesis of drugs targeting various medical conditions.
Used in Chemical Synthesis:
In the chemical synthesis industry, 3,5-dibromo-2,2,6,6-tetramethyl-4-piperidone hydrobromide is used as a building block for creating more complex molecules. Its unique structure and reactivity make it a valuable asset in the development of novel chemical products.
Used in Research and Development:
3,5-dibromo-2,2,6,6-tetramethyl-4-piperidone hydrobromide is also utilized in research and development laboratories. Its properties and reactivity are studied to understand its potential applications in various fields, including material science, pharmaceuticals, and other specialized industries.
Overall, 3,5-dibromo-2,2,6,6-tetramethyl-4-piperidone hydrobromide is a versatile compound with a wide range of applications across different industries, primarily due to its unique chemical structure and properties.

InChI:InChI=1/C9H15Br2NO.BrH/c1-8(2)6(10)5(13)7(11)9(3,4)12-8;/h6-7,12H,1-4H3;1H

Upstream product

• 826-36-8 2,2,6,6-Tetramethyl-4-piperidone 

Downstream Products

• 93969-03-0 2-(2,2,5,5-tetramethyl-2,5-dihydro-3-pyrroline-3-carbonylamino)-N-(2,6-dimethyl-phenyl)-acetamide 
• 93969-04-1 2-(2,2,5,5-tetramethyl-2,5-dihydro-3-pyrroline-3-carbonylamino)-N-(2,6-dimethylphenyl)-propionamide 
• 102132-16-1 2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid [(2,6-dimethyl-phenylcarbamoyl)-phenyl-methyl]-amide 
• 66314-86-1 cis-3,5-dibromo-4-oxo-2,2,6,6-tetramethylpiperidin-1-yloxy radical 
• 102132-14-9 2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid [2-(3,4-dimethoxy-phenyl)-ethyl]-amide 
• 93968-92-4 2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid 4-methoxy-benzylamide 
• 102132-12-7 2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid benzyl-methyl-amide 
• 102132-11-6 2,2,5,5-tetramethyl-2,5-dihydro-pyrrole-3-carboxylic acid benzylamide 
• 93968-94-6 N-[(alpha-carbamoyl)-benzyl]-2,2,5,5-tetramethyl-3-pyrroline-3-carboxamide 
• 4567-22-0 2,2,5,5-tetramethylpyrrolidine 
• 76893-27-1 (1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)methyl methanesulfonate 
• 2154-32-7 methyl 1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-carboxylate radical 
• 55738-75-5 (2,5-dihydro-2,2,5,5-tetramethyl-1-oxyl-1H-pyrrol-3-yl)methanol 
• 76893-32-8 3-(bromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-oxyl 

Relevant academic research and scientific papers

Facile synthesis of 3-formyl-2,2,5,5-tetramethyl-1-oxypyrroline

The spin-label compound 3-formyl-2,2,5,5-tetramethyl-1-oxypyrroline was synthesized from inexpensive starting materials in a sequence of four experimentally undemanding, but high yield achieving transformations. The key step is reduction of an N-methoxy-N-methylcarboxamide to an aldehyde functionality.

Synthesis and Evaluation of Voltage-Gated Sodium Channel Blocking Pyrroline Derivatives Endowed with Both Antiarrhythmic and Antioxidant Activities

Under the hypothesis that cardioprotective agents might benefit from synergism between antiarrhythmic activity and antioxidant properties, a small series of mexiletine analogues were coupled with the 2,2,5,5-tetramethylpyrroline moiety, known for its antioxidant effect, in order to obtain dual-acting drugs potentially useful in the protection of the heart against post-ischemic reperfusion injury. The pyrroline derivatives reported herein were found to be more potent as antiarrhythmic agents than mexiletine and displayed antioxidant activity. The most interesting tetramethylpyrroline congener, a tert-butyl-substituted analogue, was at least 100 times more active as an antiarrhythmic than mexiletine.

Synthesis of Chiral Spin-Labeled Amino Acids

Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide synthesis.

STABILIZER COMPOUND, LIQUID CRYSTAL COMPOSITION, AND DISPLAY ELEMENT

The present invention provides a compound represented by General Formula (I). The compound according to the present invention prevents the liquid crystal composition from being deteriorated due to light, has high compatibility with the liquid crystal composition, and does not impair the storage stability of the liquid crystal composition, thus the compound is useful as a constituent member of a liquid crystal composition. Since the liquid crystal composition and the liquid crystal display element containing the compound of the present invention exhibit UV resistance and have a high VHR, it is possible to obtain a liquid crystal display element with excellent display quality in which display defects such as burn-in and display unevenness do not occur or are suppressed.

LIQUID CRYSTAL COMPOSITION CONTAINING NITROGEN-CONTAINING CYCLIC COMPOUND AND LIQUID CRYSTAL DISPLAY DEVICE

The disclosure shows a liquid crystal composition that contains a compound having an effect of preventing photolysis of the liquid crystal composition and having high solubility in the liquid crystal composition, and that satisfies at least one of characteristics such as high maximum temperature, low minimum temperature, small viscosity, suitable optical anisotropy, large positive or negative dielectric anisotropy, large specific resistance, high stability to ultraviolet light or heat, and a suitable elastic constant, etc. and so on. The disclosure shows a liquid crystal composition that contains a compound having the following azolidine ring (Q-1) or azepane ring (Q-2), a liquid crystal display device and so on.

2′-Alkynylnucleotides: A Sequence- and Spin Label-Flexible Strategy for EPR Spectroscopy in DNA

Electron paramagnetic resonance (EPR) spectroscopy is a powerful method to elucidate molecular structure through the measurement of distances between conformationally well-defined spin labels. Here we report a sequence-flexible approach to the synthesis of double spin-labeled DNA duplexes, where 2′-alkynylnucleosides are incorporated at terminal and internal positions on complementary strands. Post-DNA synthesis copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions with a variety of spin labels enable the use of double electron-electron resonance experiments to measure a number of distances on the duplex, affording a high level of detailed structural information.

METAL AMIDES OF CYCLIC AMINES

Compounds, and oligomers of the compounds, are synthesized with cyclic amine ligands attached to a metal atom. These compounds are useful for the synthesis of materials containing metals. Examples include pure metals, metal alloys, metal oxides, metal nitrides, metal phosphides, metal sulfides, metal selenides, metal tellurides, metal borides, metal carbides, metal silicides and metal germanides. Techniques for materials synthesis include vapor deposition (chemical vapor deposition and atomic layer deposition), liquid solution methods (sol-gel and precipitation) and solid-state pyrolysis. Suitable applications include electrical interconnects in microelectronics and magnetoresistant layers in magnetic information storage devices. The films have very uniform thickness and high step coverage in narrow holes.

Facile synthesis of 3-methoxycarbonyl-2,2,5,5-tetra-methylpyrrolidine-1-oxyl and derivatives

We have achieved an efficient alternative synthesis of blood-brain-barrier permeable nitroxyl radicals 3-methoxycarbonyl-2,2,5,5-tetra-methylpyrrolidine-1-oxyl (1a) and 3-ethoxycarbonyl-2,2,5,5-tetramethylpyrroli-dine-1-oxyl (1b), which affords 1a and 1b in 65% isolated yields by four steps from 2,2,6.6-tetramethyl-4-piperidone (2), respectively. This protocol is applicable to the synthesis of 3-isopropoxy-2,2,5,5-tetramethylpyrrolidine-1-oxyl (1c) and 3-carbonyl-2,2,5,5-tetramethylpyrro-lidine-1-oxyl (6).

Synthesis of nitroxide containing polyenes: two chemically modified retinals and their interaction with bacterioopsin

The synthesis and spectroscopic characterization of two retinal analogues is described, the paramagnetic 3-pyrrolin-1-yloxy analogue 1 and its diamagnetic equivalent, the 3-pyrroline analogue 2.Various aspects of the synthesis of the aminoxy group containing polyenes are discussed.Upon interaction with bacterioopsin, both 1 and 2 are incorporated in the protein and form a system with λmax 459 nm.Neither of the two bacteriorhodopsin analogues is photoactive.ESR spectroscopy data of the system containing 1 show that the ring part of the chromophore in the protein is rigidly fixed in orientation.

ELECTROCHEMICAL CHLORINATION AND BROMINATION OF DERIVATIVES OF 2,2,6,6-TETRAMETHYLPIPERIDINE

It was shown that the direction of electrochemical chlorination and bromination in the derivatives of 2,2,6,6-tetramethylpiperidine depends on the acidity of the medium.In an acidic medium 3,5-dibromo-4-oxo-2,2,6,6-tetramethylpiperidine and 3,3,5,6-tetrachloro-4-oxo-2,2,6,6-tetramethylpiperidine respectively are formed from 4-oxo-2,2,6,6-tetramethylpiperidine; derivatives of 2,2,6,6-tetramethylpiperidine not containing a carbonyl group form perbromides during bromination under these conditions.Electrochemical chlorination and bromination in a neutral medium lead to the corresponding N-halogeno derivatives.It was established that 3,3,5,5-tetrachloro-4-oxo-2,2,6,6-tetramethylpiperidine enters into the Favorskii rearrangement with the formation of 3-hydroxy-4-oxo-2,2,5,5-tetramethylpyrrolidine-3-carboxamide.