7680-59-3

Basic information

• Product Name: 4-Amino-1-methyl-pyridiniumiodide
• Synonyms: 4-Aminopyridine methiodide;4-Amino-1-methylpyridin-1-ium iodide
• CAS NO: 7680-59-3
• Molecular Formula: C₆H₉N₂*I
• Molecular Weight: 236.06
• Mol File: 7680-59-3.mol

Chemical Properties

• Boiling Point: 255.2°C at 760 mmHg
• Flash Point: 131.8°C
• Appearance: /
• Vapor Pressure: 0.0165mmHg at 25°C
• CAS DataBase Reference: 4-Amino-1-methyl-pyridiniumiodide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-1-methyl-pyridiniumiodide(7680-59-3)
• EPA Substance Registry System: 4-Amino-1-methyl-pyridiniumiodide(7680-59-3)

Safety Data

• Hazardous Substances Data: 7680-59-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H6N2.CH3I/c6-5-1-3-7-4-2-5;1-2/h1-4H,(H2,6,7);1H3

Upstream product

• 504-24-5 4-aminopyridine 
• 74-88-4 methyl iodide 

Downstream Products

• 1025355-71-8 C₂₃H₁₉ClN₃O₂⁽¹⁺⁾*I^(1-) 

Relevant articles and documents

Synthesis and properties of aza analogs of merocyanine dyes based on N-substituted 2- and 4-aminopyridinium salts

A series of aza analogs of the merocyanine dyes based on 1-N-alkyl-2- and 1-N-alkyl-4-aminopyridinium salts and ethoxymethylidenemalononitrile was synthesized. Their physico-chemical properties were studied.

Novel C[sbnd]H???O hydrogen-bonded supramolecular complexes of 18-crown-6 with 1-alkylpyridinium iodide and its amino derivatives: Third-order nonlinear optical properties and Hirshfeld surface analysis

Five supramolecular complexes of 18-crown-6 (18C6) with 1-alkylpyridinium iodide and its amino derivatives were synthesized successfully from methanolic solution by slow evaporation solution growth technique. Crystal structure elucidated by single-crystal X-ray diffraction reveals that all the cocrystals belong to the monoclinic system. Cocrystals bis(1-methylpyridinium iodide)-18C6 (I), bis(4-amino-1-methylpyridin-1-ium iodide)-18C6 (IV), and bis(4-amino-1-ethylpyridin-1-ium iodide)-18C6 (V) crystallize centrosymmetrically with space group C2/m and other two crystals bis(2-amino-1-methylpyridin-1-ium iodide)-18C6 (II) and bis(3-amino-1-methylpyridin-1-ium iodide)-18C6 (III) crystallize in P21/n centric space group. Intra- and inter-molecular hydrogen bonding interactions and weak Van der Walls forces construct the supramolecular architecture in the crystal packing. Interestingly, all the 1-alkylpyridin-1-ium cations interact with 18C6 moiety through C-H???O hydrogen bonding interactions and N-H???O interactions are observed only in the case of (II). Fingerprint plots of Hirshfeld surfaces were used to locate and analyze the percentage of hydrogen bonding interactions. Direct band gap energies are estimated using diffuse reflectance data by the application of the Kubelka – Munk algorithm. The third-order nonlinear optical susceptibilities (χ(3)) for the compounds are, 5.57 × 10?6 esu for (I), 3.62 × 10?6 esu for (II), 4.37 × 10?6 esu for (III), 5.30 × 10?6 esu for (IV), and 4.24 × 10?6 esu for (V), respectively.

Effect of intercalation and chromophore arrangement on the linear and nonlinear optical properties of model aminopyridine push-pull molecules

Three push-pull aminopyridine derivatives having D-π-A, D-(π-A)2, and D-(π-A)3 arrangements were examined as model organic chromophores capable of intercalation into inorganic layered materials (alpha modification of zirconium hydrogen phosphate, zirconium 4-sulfophenylphosphonate, and gamma modification of titanium hydrogen phosphate). The fundamental properties of these dyes, their methylated analogues as well as their intercalates were studied by X-ray analysis, electrochemistry, UV/Vis absorption spectra, TGA, IR spectra, SHG, and were completed by DFT calculations. The synthesis of tripodal tris(pyridin-4-yl)amine is given for the first time. The HOMO-LUMO gap, the position of the longest-wavelength absorption maxima, and the dipole moment of aminopyridines can easily be tuned by attaching/removing pyridin-4-yl electron withdrawing units and their quaternization (pyridine vs. pyridinium acceptors). Their intercalation proved to be feasible affording novel inorganic-organic hybrid materials. The intercalation is accompanied by protonation of the guest, which enhances its ICT and strongly anchors the aminopyridines into the confined space of the layered host. Moreover, this process results in ordering of the organic chromophores and also brings improved thermal and chemical robustness. As a result, the measured SHG efficiencies of the intercalates are larger than those observed for the pure organic push-pull chromophores. Hence, the methodology of intercalation turned out to be very useful strategy for property tuning of NLO-active organic molecules.

Excellent correlation between substituent constants and pyridinium N-methyl chemical shifts

Substituents on the pyridinium ring of N-methylpyridinium derivatives, especially those on the 2- or 4-position, have a large effect on the 1H and 13C NMR chemical shifts of the N-methyl group. Reasonable correlations between the chemical shift changes and the resonance substituent constants are observed. The dual substituent parameter approach provides an excellent correlation when a combination of polar and resonance substituent constants is employed.

Second-order hyperpolarizability of pyridinium cations

The second-order hyperpolarizability (β) of pyridinium cations with cutoff (λco) shorter than 400 nm were studied by semiempirical calculation and the hyper-Rayleigh scattering (HRS) technique. The β value of 4-dimethylaminopyridinium (λco= 390 nm) was evaluated to be about 1.5 times larger than that of p-nitroaniline (λco= 473 nm) in methanolic solution using 1064 nm light as a fundamental beam.