3376-50-9

Basic information

• Product Name: 2,4,6-trimethylpyridine 1-oxide
• Synonyms: 2,4,6-trimethylpyridine 1-oxide;Einecs 222-169-1;2,4,6-trimethyl-1-oxidopyridin-1-ium
• CAS NO: 3376-50-9
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.17904
• EINECS: 222-169-1
• Mol File: 3376-50-9.mol

Chemical Properties

• Boiling Point: 303°Cat760mmHg
• Flash Point: 137.1°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 0.00171mmHg at 25°C
• Refractive Index: 1.507
• PKA: pK1:1.990(+1) (25°C)
• CAS DataBase Reference: 2,4,6-trimethylpyridine 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-trimethylpyridine 1-oxide(3376-50-9)
• EPA Substance Registry System: 2,4,6-trimethylpyridine 1-oxide(3376-50-9)

Safety Data

• Hazardous Substances Data: 3376-50-9(Hazardous Substances Data)

Usage

Uses

Used in Solvent Applications:
2,4,6-Trimethylpyridine 1-oxide is used as a solvent for various chemical processes due to its ability to dissolve a wide range of substances, enhancing the efficiency and effectiveness of these processes.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,4,6-trimethylpyridine 1-oxide is used as a key intermediate in the synthesis of certain drugs, contributing to the development of new medications and therapies.
Used in Agrochemical Production:
2,4,6-trimethylpyridine 1-oxide is also utilized in the production of agrochemicals, playing a crucial role in the development of pesticides and other agricultural products that help increase crop yields and protect plants from pests.
Used as a Corrosion Inhibitor:
2,4,6-Trimethylpyridine 1-oxide serves as a corrosion inhibitor, protecting metal surfaces from degradation and extending the lifespan of industrial equipment and structures.
Used in Specialty Industrial Products:
This versatile compound can be found in various specialty industrial products, where its unique properties contribute to the performance and quality of these applications.
Used in Cancer Treatment Research:
2,4,6-Trimethylpyridine 1-oxide has been studied for its potential use in treating certain types of cancer, leveraging its unique chemical properties to target and combat cancer cells, offering hope for new therapeutic approaches in oncology.

InChI:InChI=1/C8H11NO/c1-6-4-7(2)9(10)8(3)5-6/h4-5H,1-3H3

Upstream product

• 108-75-8 2,4,6-trimethyl-pyridine 
• 139-66-2 diphenyl sulfide 
• 1003-67-4 4-methylpyridine-1-oxide 
• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 
• 940-93-2 2,4,6-trimethylpyrylium chlorate(VII) 

Downstream Products

• 81540-94-5 4,6-dimethyl-2-phenacylpyridine 1-oxide 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 113708-05-7 4,6-dimethyl-2-(5-pyrimidinyl)pyridine 
• 113708-06-8 2,6-dimethyl-4-(5-pyrimidinyl)pyridine 
• 4472-55-3 4,6-dimethyl-pyridin-2-ylmethyl chloride 
• 120739-87-9 2,6-dimethyl-pyridin-4-ylmethyl chloride 
• 111172-57-7 triphenyltin isoselenocyanate * 2,4,6-collidine-N-oxide 
• 18087-99-5 4,6-dimethyl-2-(hydroxymethyl)pyridine 
• 5439-01-0 4,6-dimethylpyridine-2-carbaldehyde 

Relevant articles and documents

Chalcogen-Bonded Cocrystals of Substituted Pyridine N-Oxides and Chalcogenodiazoles: An X-ray Diffraction and Solid-State NMR Investigation

We introduce methyl, methoxy, and phenyl substituents at the para-, meta-, and ortho- positions of pyridine N-oxide to investigate the effect of chemical substitution on the resulting nine chalcogen-bonded structures formed upon cocrystallization with 3,4-dicyano-1,2,5-selenodiazole and 3,4-dicyano-1,2,5-telluradiazole. Single-crystal X-ray diffraction studies reveal the presence of double chalcogen bonding interactions in the cocrystals and demonstrate the impact of the substitution on the geometric features of the chalcogen bonds. 77Se and 125Te solid-state NMR spectroscopy is employed to measure selenium and tellurium chemical shift tensors of the products, and various trends are described. The smallest component of the 77Se chemical shift tensor (δ33) provides the strongest correlation with the chalcogen bond distance. Solution NMR provides qualitative evidence for the persistence of the chalcogen bonds in solution. Finally, 1J(77Se,14N) coupling constants in 3,4-dicyano-1,2,5-selenodiazole and its chalcogen-bonded cocrystals are measured after accounting for residual dipolar coupling between 77Se and 14N; however, changes in 1J(77Se,14N) attributable to chalcogen bonding upon cocrystallization are comparable to the experimental uncertainties. This systematic study of chalcogen-bonded cocrystals demonstrates the potential utility of the substitution effect for applications of chalcogen bonds in crystal engineering and demonstrates the value of solid-state NMR in characterizing such systems.

A mild and efficient H2O2 oxygenation of N-heteroaromatic compounds to the amine N-oxides and KI deoxygenation back to the tertiary amine with hexaphenyloxodiphosphonium triflate

A mild and efficient method for the oxidation of N-heteroaromatic compounds to the corresponding N-oxides using H2O2 in the presence of hexaphenyloxodiphosphnium triflate (Hendrickson reagent) in EtOH at room temperature was reported. This methodology presented relatively fast and selective reactions to afford the N-oxides in good yields. The reverse reactions, deoxygenation reactions, were also carried out under the same reaction conditions by KI to produce the tertiary amines.

A pyridine nitrogen oxide high-efficient, multi-phase catalytic preparation method

The invention discloses a high efficient heterogeneous catalytic preparation method of pyridine oxynitride. In the provided preparation method, mono-substituted or poly-substituted pyridines or pyridine derivatives are taken as the primary raw materials, titanium dioxide loaded on tungsten (WO3/TiO2) is taken as the catalyst, hydrogen peroxide is taken as the oxidizing agent, and reactions are carried out in a water solution at a room temperature so as to obtain the target product. Compared with the prior art, the preparation method has the following advantages: (1) the provided oxidation method, no acetic acid is used, and thus the requirements on equipment are greatly reduced; (2) a heterogeneous catalytic method is adopted to prepare pyridine oxynitride, the catalyst can be separated from the reaction system through simple filtration or centrifugation, and the operation is convenient; (3) titanium dioxide loaded on tungsten is taken as the catalyst, pyridine oxynitride is prepared by one step in a water solution at a room temperature, the reaction conditions are mild, and the pollution to the environment is little.

A lipase-glucose oxidase system for the efficient oxidation of: N -heteroaromatic compounds and tertiary amines

In this work, a lipase-glucose oxidase system has been designed and proven to be an efficient system for the oxidation of N-heteroaromatic compounds and tertiary amines. This dual-enzyme system not only displays environmental friendliness, but also demonstrates its huge potential in industrial applications.

A chemical chaperone-based drug candidate is effective in a mouse model of amyotrophic lateral sclerosis (ALS)

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the selective death of motor neurons and skeletal muscle atrophy. The majority of ALS cases are acquired spontaneously, with inherited disease accounting for only 10 % of all cases. Recent studies provide compelling evidence that aggregates of misfolded proteins underlie both types of ALS. Small molecules such as artificial chaperones can prevent or even reverse the aggregation of proteins associated with various human diseases. However, their very high active concentration (micromolar range) severely limits their utility as drugs. We synthesized several ester and amide derivatives of chemical chaperones. The lead compound 14, 3-((5-((4,6-dimethylpyridin-2-yl)methoxy)-5-oxopentanoyl)oxy)-N,N-dimethylpropan-1-amine oxide shows, in the micromolar concentration range, both neuronal and astrocyte protective effects in vitro; at daily doses of 10 mg kg-1 14 improved the neurological functions and delayed body weight loss in ALS mice. Members of this new chemical chaperone derivative class are strong candidates for the development of new drugs for ALS patients.

Metal-free methylation of a pyridine N-oxide C-H bond by using peroxides

Metal-free methylation of a pyridine N-oxide C-H bond was developed using peroxide as a methyl reagent under neat conditions. Pyridine N-oxide derivatives with various groups (e.g., Cl, NO2, and OCH3) were all suitable substrates, and the desired products were obtained in moderate to excellent yields under standard conditions. Moreover, the methylation can be performed with a good yield on the gram-scale experiment. Tentative mechanistic studies show that the methylation is a classical radical process.

TAPC-promoted oxidation of sulfides and deoxygenation of sulfoxides

Figure presented. 1,3,5-Triazo-2,4,6-triphosphorine-2,2,4,4,6,6- tetrachloride (TAPC) was found to be an efficient promoter for the oxidation of sulfides and deoxygenation of sulfoxides. Excellent yields, short reaction time, easy and quick isolation of the products, solvent-free process, and excellent chemoselectivity are the main advantages of this procedure.

Bioavailable diacylhydrazine ligands for modulating the expression of exogenous genes via an ecdysone receptor complex

The present invention relates to non-steroidal ligands for use in nuclear receptor-based inducible gene expression system, and a method to modulate exogenous gene expression in which an ecdysone receptor complex comprising: a DNA binding domain; a ligand binding domain; a transactivation domain; and a ligand is contacted with a DNA construct comprising: the exogenous gene and a response element; wherein the exogenous gene is under the control of the response element and binding of the DNA binding domain to the response element in the presence of the ligand results in activation or suppression of the gene.

Beckmann and cyclization reactions of δ-oxo-α,β- unsaturated ketoximes obtained from pyrylium salts and hydroxylamine. Formation of 2-aryl(or alkyl)amino-4,6- disubstituted pyrylium salts

The reaction of 2,4,6-trisubstituted pyrylium salts 1 with hydroxylamine gave regio- and stereo-selectively 1,3,5- trisubstituted 2-cis-pentene-1,5-dione 1-oximes 4. On cyclization, 3,5,5-trisubstituted 2-isoxazolines 6 and 2,4,6- trisubstituted pyridine 1-oxides 5 were obtained, originating in the anti/syn stereoisomers of oxime 4, respectively. Beckmann reaction of keto-ketoximes 4 with thionyl chloride unexpectedly gave 2-aryl (or alkyl)amino-4,6-disubstituted pyrylium salts 7, the first example of rearrangement/cyclization involving carbonylic oxygen as terminator. Crystallographic data are provided for (Z)-N-t-butyl-3,6,6-trimethyl-2-heptenecarboxamide 13b.

Reaction of pyrylium salts with nucleophiles. Part 25. Formation of pyridine-1-oxides, 2-isoxazolines and 1-pyrazoline-1-oxides

The reaction of tri- and tetrasubstituted pyrylium salts with hydroxylamine affords acyclic keto-ketoximes (to be described in a separate paper) which cyclize yielding pyridine-1-oxides and/or 2-isoxazolines. Both these classes of compounds, with many possible applications, can thus be obtained simply and in good yield. The regioselectivity of 2-isoxazoline formation from unsymetrically substituted pyrylium salts is discussed. An unprecedented minor product formed from 2,6-di-t-butyl-4-methylpyrylium perchlorate and two molecules of hydroxylamine is the corresponding 1- pyrazoline-1-oxide. Mechanistic rationalization of all products are provided.