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
• Article Data: 2

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

General Description

4-Amino-3,5-dimethylpyridine 1-oxide is a chemical compound with the molecular formula C7H10N2O. It is a derivative of pyridine and is commonly used as a reagent in organic synthesis. 4-aMino-3,5-diMethylpyridine1-oxide is a white solid that is soluble in water and other polar solvents. It has been used in pharmaceutical research and as a building block in the preparation of various organic compounds. Additionally, 4-Amino-3,5-dimethylpyridine 1-oxide has potential applications in the field of medicinal chemistry and may be utilized in the development of new drugs. However, it is important to handle and use this compound with caution, as it may pose health and safety hazards if not handled properly.

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).