43078-60-0

Basic information

• Product Name: 3,5-dimethylpyridin-4-amine
• Synonyms: 4-Amino-3,5-dimethylpyridine;3,5-Dimethylpyridin-4-ylamine;3,5-Dimethyl-pyridine-4-yl-amine;3.5-Dimethyl-4-aminopyridine;3,5-diMethyl-4-PyridinaMine;5-diMethylpyridin-4-aMine;3,5-DiMethyl-pyridin-4-ylaMine.HCl;4-PyridinaMine, 3,5-diMethyl-
• CAS NO: 43078-60-0
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.17
• Product Categories: Building Blocks;Pyridine
• Mol File: 43078-60-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 104-106℃
• Boiling Point: 277.801 °C at 760 mmHg
• Flash Point: 146.292 °C
• Appearance: /
• Density: 1.04 g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: pK1: 9.54(+1) (20°C)
• CAS DataBase Reference: 3,5-dimethylpyridin-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-dimethylpyridin-4-amine(43078-60-0)
• EPA Substance Registry System: 3,5-dimethylpyridin-4-amine(43078-60-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 43078-60-0(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C7H10N2/c1-5-3-9-4-6(2)7(5)8/h3-4H,1-2H3,(H2,8,9)

Upstream product

• 76139-65-6 4-amino-3,5-dimethylpyridine 1-oxide 
• 3718-65-8 3,5-Dimethylpyridine N-oxide 
• 14248-66-9 3,5-dimethyl-4-nitropyridine-1-oxide 

Downstream Products

• 252641-90-0 C₆H₁₀(C₆H₂(CH₃)2NHC(O)C₅H₃NC(O)NHC₅H₂(CH₃)2N)2 
• 252641-89-7 [(CH₃)2C₅NH₂NHCOC₅NH₃CONHC₆H₂(CH₃)2]2C₄H₈ 
• 215361-23-2 N,N'-bis(3,5-dimethylpyridin-4-yl)-pyridine-2,6-dicarboxamide 
• 633296-23-8 N-(4-iodo-2,6-diisopropylphenyl)-N-(3,5-dimethylpyridin-4-yl)pyridine-2,6-dicarboxamide 
• 37669-66-2 4-fluoro-3,5-dimethylpyridine 
• 633296-24-9 pyridine-2,6-dicarboxylic acid 2-({2,6-diisopropyl-4-[(triisopropylsilanyl)-ethynyl]-phenyl}-amide) 6-[(3,5-dimethyl-pyridin-4-yl)-amide] 
• 633296-25-0 N-(4-ethynyl-2,6-diisopropylphenyl)-N-(3,5-dimethylpyridin-4-yl)pyridine-2,6-dicarboxamide 

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).