3718-65-8

Basic information

• Product Name: 3,5-DIMETHYLPYRIDINE-N-OXIDE
• Synonyms: RARECHEM AQ NN 0181;3,5-DIMETHYLPYRIDINE-N-OXIDE;3,5-LUTIDINE N-OXIDE;3,5-Dimethylpyridine 1-oxide;3,5-Dimethylpyridine-1-oxide;3,5-Dimethylpyridinium-1-olate;3,5-dimethyl-1-oxidanidyl-pyridin-1-ium;3,5-dimethyl-1-oxido-pyridin-1-ium
• CAS NO: 3718-65-8
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• Product Categories: Heterocyclic Compounds;C7 and C8;Heterocyclic Building Blocks;Pyridines
• Mol File: 3718-65-8.mol

Chemical Properties

• Melting Point: 100-104 °C(lit.)
• Boiling Point: 168°C/23mmHg(lit.)
• Flash Point: 129.4°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 0.00362mmHg at 25°C
• Refractive Index: 1.509
• PKA: pK1:1.181(+1) (25°C)
• CAS DataBase Reference: 3,5-DIMETHYLPYRIDINE-N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHYLPYRIDINE-N-OXIDE(3718-65-8)
• EPA Substance Registry System: 3,5-DIMETHYLPYRIDINE-N-OXIDE(3718-65-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 3718-65-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3,5-Dimethylpyridine N-Oxide is used as a reagent for the synthesis of 3,5-Dimethyl-4-nitropyridine 1-Oxide (D473635), which is an intermediate in the production of 2-[(2-pyridylmethyl)thio or -sulfinyl]benzimidazoles. These benzimidazoles are known for their antiulcer properties, making 3,5-Dimethylpyridine N-Oxide a valuable component in the development of pharmaceuticals aimed at treating ulcers.
Used in Polymer Synthesis:
In the polymer industry, 3,5-Dimethylpyridine N-Oxide may be utilized to synthesize isotactic poly(N-isopropylacrylamide)s (NIPAAm). These polymers have unique properties, such as temperature sensitivity, which makes them suitable for various applications, including drug delivery systems and smart materials.

InChI:InChI=1/C7H9NO/c1-6-3-7(2)5-8(9)4-6/h3-5H,1-2H3

Synthetic route

3,5-Lutidine (591-22-0) → 3,5-Dimethylpyridine N-oxide (3718-65-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In Isopropyl acetate at 10 - 35℃; for 5.83333h; Green chemistry;	98.3%
With peracetic acid at 85℃; for 2h;	97.5%
With dihydrogen peroxide; acetic acid at 80℃; for 18h;	95%

3,5-Dimethylpyridine N-oxide (3718-65-8) → 6,8-dimethyl-tetrazolo[1,5-a]pyridine

Conditions	Yield
With pyridine; diphenyl phosphoryl azide at 120℃; for 24h;	96%

Upstream product

• 591-22-0 3,5-Lutidine 

Downstream Products

• 73028-02-1 3-(4-chloro-phenyl)-6,7a-dimethyl-(3ar,7ac)-3a,7a-dihydro-3H-oxazolo[4,5-b]pyridin-2-one 
• 73028-00-9 3-(2-chloro-phenyl)-6,7a-dimethyl-(3ar,7ac)-3a,7a-dihydro-3H-oxazolo[4,5-b]pyridin-2-one 
• 73028-03-2 6,7a-dimethyl-3-(2-nitro-phenyl)-(3ar,7ac)-3a,7a-dihydro-3H-oxazolo[4,5-b]pyridin-2-one 
• 54903-99-0 6,8-dimethyl-1-phenyl-1,8a-dihydro-[1,2,4]oxadiazolo[2,3-a]pyridin-2-one 
• 59346-32-6 6,7a-dimethyl-3-phenyl-3a,7a-dihydro-3H-oxazolo[4,5-b]pyridin-2-one 
• 73027-99-3 6,7a-dimethyl-3-p-tolyl-(3ar,7ac)-3a,7a-dihydro-3H-oxazolo[4,5-b]pyridin-2-one 
• 73027-97-1 6,7a-dimethyl-3-o-tolyl-(3ar,7ac)-3a,7a-dihydro-3H-oxazolo[4,5-b]pyridin-2-one 
• 59346-33-7 3-(4-bromo-phenyl)-6,7a-dimethyl-3a,7a-dihydro-3H-oxazolo[4,5-b]pyridin-2-one 
• 73028-01-0 3-(3-chloro-phenyl)-6,7a-dimethyl-(3ar,7ac)-3a,7a-dihydro-3H-oxazolo[4,5-b]pyridin-2-one 
• 112251-38-4 (4aS,5aS,8aR,8bS)-3,4a-Dimethyl-7-phenyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 112251-40-8 (4aS,5aS,8aR,8bS)-3,4a-Dimethyl-7-o-tolyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 112251-39-5 (4aS,5aS,8aR,8bS)-7-(4-Methoxy-phenyl)-3,4a-dimethyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 140934-66-3 (3aR,7aS)-3-Benzenesulfonyl-2,6,7a-trimethyl-3a,7a-dihydro-furo[3,2-b]pyridine 
• 112251-46-4 (4aS,5aS,8aR,8bS)-3,4a-Dimethyl-7-(2-nitro-phenyl)-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 

Relevant articles and documents

Molecular energetics of alkyl substituted pyridine N-oxides: An experimental study

The standard (p° = 0.1 MPa) energies of combustion in oxygen, at T = 298.15 K, for the solid compounds 2-methylpyridine-N-oxide (2-MePyNO), 3-methylpyridine-N-oxide (3-MePyNO) and 3,5-dimethylpyridine-N-oxide (3,5-DMePyNO) were measured by static-bomb calorimetry, from which the respective standard molar enthalpies of formation in the condensed phase were derived. The standard molar enthalpies of sublimation, at the same temperature, were measured by Calvet microcalorimetry. From the standard molar enthalpy of formation in gaseous phase, the molar dissociation enthalpies of the N-O bonds were derived, and compared with values of the dissociation enthalpies of other N-O bonds available for other pyridine-N-oxide derivatives.

Method for synthesizing pyridine-N-oxide through catalytic oxidation by continuous non-solvent method

The invention discloses a method for synthesizing pyridine-N-oxide through catalytic oxidation by a continuous non-solvent method, and belongs to the field of chemical synthesis. The method is characterized by comprising the following steps: mixing metered pyridine or alkyl pyridine with an oxidizing agent in proportion, carrying out a reaction in a continuous tubular reactor filled with an immobilized catalyst, and distilling off excess water after the reaction is finished to obtain a pyridine-N-oxide or alkyl pyridine-N-oxide product, wherein the catalyst is cross-linked polystyrene resin immobilized with active substance anions and has a quaternary ammonium salt group. Compared with the prior art, the method for synthesizing the pyridine-N-oxide through catalytic oxidation by the continuous non-solvent method can realize continuous production of the pyridine-N-oxide, is environment-friendly, energy-saving and high in conversion rate, and has very good promotion and application values.

The M?CPbA?NH3(G) system: A safe and scalable alternative for the manufacture of (substituted) pyridine and quinoline N?oxides?

An improved, safe, and scalable isolation process for (substituted) pyridine and quinoline N-oxides in quantitative yields along with high purities using the m-CPBA?NH3(g) system is described. The safety was assessed by reaction calorimetry and differential scanning calorimetry studies for possible hazards during the conversion and isolation steps. Careful interpretation of the data substantiated the safety and scalability. The process flow is simplified to meet the industrial requirements of safety, cost-effectiveness, and utility minimization. The reaction was safely demonstrated at a 2.5 kg scale.

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.

Catalyst-free and selective oxidation of pyridine derivatives and tertiary amines to corresponding N-oxides with 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane

The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields. Graphical abstract: The catalyst-free oxidation of various pyridine derivatives and tertiary amines to their corresponding N-oxides with 1,1,2,2-tetrahydroperoxy-1,2-diphenylethane as an efficient oxidant has been developed. The methodology proved to tolerate a number of functional groups. The reactions proceeded smoothly under solvent-free and mild conditions at room temperature. All the products were easily extracted from the reaction mixtures in excellent yields.

DIMETHYLBENZOIC ACID COMPOUNDS

The present invention provides a compound of the Formula I: wherein A is: and W, Y, X, R1, R2, R3, and R4 are as defined herein, or a pharmaceutically acceptable salt thereof, for use as an inhibitor of the EP4 receptor.

Controlled oxygen release from pyridone endoperoxides promotes cell survival under anoxic conditions

In tissue engineering, survival of larger constructs remains challenging due to limited supply of oxygen caused by a lack of early vascularization. Controlled release of oxygen from small organic molecules represents a possible strategy to prevent cell death under anoxic conditions. A comprehensive study of methylated pyridone-derived endoperoxides has led to the development of water-soluble molecules that undergo retro-Diels-Alder reactions in aqueous environment releasing oxygen in high yield and with half-lives of up to 13 h. These molecules in combination with vitamin C as singlet oxygen quencher significantly improved survival of 3T3 fibroblasts and rat smooth muscle cells challenged with oxygen-depleted conditions.

PYRIDINE- 2- DERIVATIVES AS SMOOTHENED RECEPTOR MODULATORS

The present application relates to compounds of Formula (I), and Formula (II), or pharmaceutically acceptable salt thereof, wherein A, X, Y, Z, e, f, R1, R2, R3, R4, R5, R5b, R6, R7, R8, R9, R10, R11,R20, R21, R22 and R23 are defined herein. These novel pyridine derivatives that are useful in therapy, in particular for treating diseases or conditions mediated by Smo, including the treatment of abnormal cell growth, such as cancer, in mammals. Additional embodiments relate to methods of using such compounds in the treatment of abnormal cell growth in mammals, especially humans, and to pharmaceutical compositions containing such compounds.

Syntheses of sterically hindered zwitterionic pyridinium phenolates as model compounds in nonlinear optics

Pyridinium phenolates possess a dissymmetric delocalised π-electron system providing a huge quadratic nonlinearity. They are a promising class of molecules for applications in photoelectronics and photonics. Semiempirical calculations indicate that the interplanar angle between the two aromatic rings leads to enhancement in the NLO properties of these compounds. The confirmation of this feature may be provided by the study of a new series of sterically hindered pyridinium phenolates 2a-e bearing two tert-butyl substituents at the ortho position(s) of the phenolate functionality. Such bulky groups would enhance the solubility of zwitterions in organic solvents and would limit the formation of aggregates. Their efficient preparations by using Suzuki cross-coupling reactions involving 3,5-dialkylated 4-bromopyridine N-oxides are described herein. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

NOVEL SULFONYL DERIVATIVES

Sulfonyl derivatives represented by the following general formula (I): Q1-Q2-T1-Q3-SO2-QA and drugs containing the same (wherein Q1 is an optionally substituted, saturated or unsaturated, five- or six-membered cyclic hydrocarbon group, a five- or six-membered heterocyclic group, or the like; Q2 is a single band, oxygen, sulfur, C1-C6 alkylene or the like; QA is optionally substituted arylalkenyl, heteroarylalkenyl or the like; and T1 is carbonyl or the like). These compounds have potent FXa-inhibitory effects and promptly exert satisfactory and persistent antithrombotic effects through oral administration, thus being useful as anticoagulant agents little accompanied with side effects.