76139-65-6

Basic information

• Product Name: 4-aMino-3,5-diMethylpyridine1-oxide
• Synonyms: 4-aMino-3,5-diMethylpyridine1-oxide;4-PyridinaMine, 3,5-diMethyl-, 1-oxide
• CAS NO: 76139-65-6
• Molecular Formula: C7H10N2O
• Molecular Weight: 138.1671
• Mol File: 76139-65-6.mol

Chemical Properties

• Boiling Point: 229.6°Cat760mmHg
• Flash Point: 92.7°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 0.0132mmHg at 25°C
• Refractive Index: 1.558
• PKA: 4.19±0.10(Predicted)
• CAS DataBase Reference: 4-aMino-3,5-diMethylpyridine1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-aMino-3,5-diMethylpyridine1-oxide(76139-65-6)
• EPA Substance Registry System: 4-aMino-3,5-diMethylpyridine1-oxide(76139-65-6)

Safety Data

• Hazardous Substances Data: 76139-65-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Amino-3,5-dimethylpyridine 1-oxide is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the formation of complex organic molecules.
Used in Pharmaceutical Research:
In pharmaceutical research, 4-Amino-3,5-dimethylpyridine 1-oxide is used as a building block in the preparation of organic compounds with potential therapeutic properties, contributing to the discovery and development of new drugs.
Used in Medicinal Chemistry:
4-Amino-3,5-dimethylpyridine 1-oxide is utilized in medicinal chemistry for its potential applications in the development of new drugs, where its unique structure and reactivity can be leveraged to create novel pharmaceutical agents.

InChI:InChI=1/C7H10N2O/c1-5-3-9(10)4-6(2)7(5)8/h3-4,8,10H,1-2H3

Upstream product

• 14248-66-9 3,5-dimethyl-4-nitropyridine-1-oxide 
• 3718-65-8 3,5-Dimethylpyridine N-oxide 

Downstream Products

• 43078-60-0 4-amino-3,5-dimethylpyridine 

Relevant articles and documents

Single-step versus stepwise two-electron reduction of polyarylpyridiniums: Insights from the steric switching of redox potential compression

Contrary to 4,4′-dipyridinium (i.e., archetypal methyl viologen), which is reduced by two single-electron transfers (stepwise reduction), the 4,1′-dipyridinium isomer (so-called "head-to-tail" isomer) undergoes two electron transfers at apparently the same potential (single-step reduction). A combined theoretical and experimental study has been undertaken to establish that the latter electrochemical behavior, also observed for other polyarylpyridinium electrophores, is due to potential compression originating in a large structural rearrangement. Three series of branched expanded pyridiniums (EPs) were prepared: N-aryl-2,4,6-triphenylpyridiniums (Ar-TP), N-aryl-2,3,4,5,6-pentaphenylpyridiniums (Ar-XP), and N-aryl-3,5-dimethyl-2,4,6- triphenylpyridinium (Ar-DMTP). The intramolecular steric strain was tuned via N-pyridinio aryl group (Ar) phenyl (Ph), 4-pyridyl (Py), and 4-pyridylium (qPy) and their bulky 3,5-dimethyl counterparts, xylyl (Xy), lutidyl (Lu), and lutidylium (qLu), respectively. Ferrocenyl subunits as internal redox references were covalently appended to representative electrophores in order to count the electrons involved in EP-centered reduction processes. Depending on the steric constraint around the N-pyridinio site, the two-electron reduction is single-step (Ar = Ph, Py, qPy) or stepwise (Ar = Xy, Lu, qLu). This steric switching of the potential compression is accurately accounted for by ab initio modeling (Density Functional Theory, DFT) that proposes a mechanism for pyramidalization of the Npyridinio atom coupled with reduction. When the hybridization change of this atom is hindered (Ar = Xy, Lu, qLu), the first reduction is a one-electron process. Theory also reveals that the single-step two-electron reduction involves couples of redox isomers (electromers) displaying both the axial geometry of native EPs and the pyramidalized geometry of doubly reduced EPs. This picture is confirmed by a combined UV-vis-NIR spectroelectrochemical and time-dependent DFT study: comparison of in situ spectroelectrochemical data with the calculated electronic transitions makes it possible to both evidence the distortion and identify the predicted electromers, which play decisive roles in the electron-transfer mechanism. Last, this mechanism is further supported by in-depth analysis of the electronic structures of electrophores in their various reduction states (including electromeric forms).

Studies on Diazepines. XXVI. Syntheses of 6H-1,4-Diazepines and 1-Acyl-1H-1,4-diazepines from 4-Pyridyl Azides

Photolysis of 4-azidopyridines (7a-e) in the presence of methoxide ions resulted in ring expansion to give 5-methoxy-6H-1,4-diazepines (10a-e), presumably via the azirine intermediates 8 derived from the initially formed singlet pyridylnitrenes.Treatment