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
• Article Data: 25

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

Description

3,5-Dimethylpyridine N-Oxide is an organic compound with the molecular formula C7H9NO. It is a derivative of pyridine, featuring two methyl groups at the 3rd and 5th positions and an oxide group attached to the nitrogen atom. 3,5-DIMETHYLPYRIDINE-N-OXIDE is known for its potential applications in various chemical and pharmaceutical processes due to its unique structural properties.

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

• 41995-30-6 2-amino-3,5-dimethylpyridine 
• 140934-67-4 (2aS,4aS,7aR)-7-Benzenesulfonyl-1-[1-benzenesulfonyl-meth-(E)-ylidene]-3,4a,6-trimethyl-2,2a,4a,7a-tetrahydro-1H-5-oxa-7b-aza-cyclobuta[e]indene 
• 91219-89-5 3,5-dimethyl-4-methoxypyridine 1-oxide 
• 591-22-0 3,5-Lutidine 
• 1220182-81-9 Mn(1,4-benzenedicarboxylato)(3,5-dimethyl-pyridine N-oxide) 
• 22931-88-0 3,5-dimethyl-2-ethoxycarbonylaminopyridine 

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.

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.

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.