2525-19-1

Basic information

• Product Name: 1,2,6-trimethylpyridinium iodide
• Synonyms: 1,2,6-Trimethylpyridinium iodide; pyridinium, 1,2,6-trimethyl-, iodide (1:1)
• CAS NO: 2525-19-1
• Molecular Formula: C₈H₁₂N*I
• Molecular Weight: 249.092
• Mol File: 2525-19-1.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 1,2,6-trimethylpyridinium iodide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,6-trimethylpyridinium iodide(2525-19-1)
• EPA Substance Registry System: 1,2,6-trimethylpyridinium iodide(2525-19-1)

Safety Data

• Hazardous Substances Data: 2525-19-1(Hazardous Substances Data)

Usage

General Description

1,2,6-trimethylpyridinium iodide is a chemical compound with the molecular formula C9H13IN. It is a quaternary ammonium salt consisting of a pyridinium cation and iodide anion. 1,2,6-trimethylpyridinium iodide is commonly used as a phase-transfer catalyst, enabling reactions between immiscible phases such as aqueous and organic solvents. It is also utilized in organic synthesis as a reagent for various transformations, including N-alkylation and N-oxidation reactions. 1,2,6-trimethylpyridinium iodide has also shown potential as an antimicrobial agent and has been studied for its potential use in pharmaceuticals and industry.

Upstream product

• 108-48-5 2,6-dimethylpyridine 
• 74-88-4 methyl iodide 
• 152119-73-8 6-methylbenzo<1,5>naphthyridine 

Downstream Products

• 106547-87-9 2,6-bis-(4-diethylamino-trans-styryl)-1-methyl-pyridinium; iodide 

Relevant articles and documents

Synthesis, absorption and fluorescence spectral characteristics of trinucleus dimethine cyanine dyes as fluorescent probes for DNA detection

The preparation of six trinucleus dimethine cyanine dyes with pyridine nucleus obtained by the condensation of trimethylpyridinium iodides with heterocyclic aromatic aldehyde was described. The absorption and fluorescence properties of the dyes were studied in different polarity solvents. Blue shift of the maxima absorption of the dyes was observed with the increase of solvents polarity. The fluorescence properties of the dyes in solution and in presence of DNA were studied. Significant enhancement of the fluorescent quantum yield was observed in four dyes in the presence of DNA. Specially, one of six dyes emitted weak fluorescence in Tris-HCl buffer, but displayed bright fluorescence in the presence of DNA.

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A study on a telo21 G-quadruplex DNA specific binding ligand: Enhancing the molecular recognition ability: Via the amino group interactions

A symmetric ligand is synthesized composed of a core N-methylpyridinium scaffold and two para-substituted benzyl groups through a flexible ethylene bridge to form a novel three-ring-conjugated system. The ligand system was found to have only weak background fluorescent signal in aqueous or physiological conditions and exhibited strong fluorescent signal enhancement targeting at telo21 G-quadruplex structure rather than other types of nucleic acids. The comparison study with two terminal groups (-N(CH3)2versus -SCH3) indicates that the stimulated signal enhancement of specific binding is probably attributed to the hydrogen-bonding interactions through the amino groups in the G-quartets. The docking result illuminates the experimental observation that the ligand system showed only weak fluorescent signals in aqueous or physiological conditions while exhibiting a strong fluorescent signal upon binding to the telo21 G-quadruplex structure (binding energy: -6.2 kcal mol-1).

Biomolecular recognition at the cellular level: Geometrical and chemical functionality dependence of a low phototoxic cationic probe for DNA imaging

A combined approach was adopted to understand the impact of structural geometry as well as suitable chemical functionality of a molecular probe on its efficient binding in the minor groove of DNA. The development of a small chemical library of different lutidinium conjugates (P1-P5) and molecular simulations using DFT calculations clearly demonstrated that the semilunar conformation of a molecular probe equipped with requisite chemical functionality is the key parameter for its proper binding in the minor groove of DNA. The comparative optical responses of these probes (P1-P5) coupled with the theoretical studies illustrated that only P3 displayed considerable fluorescence enhancement in the presence of DNA because of its semilunar geometry and special chemical architecture. Furthermore, the bioassays clearly revealed that the probe can penetrate the cell membrane of live as well as dead cells without the help of any permeabilization agent. Microscopic cellular imaging established that probe P3 can stain the nuclear region of the cells with high contrast and negligible cytoplasmic spillage without causing any cellular deterioration. The specificity and binding efficiency of P3 toward DNA were established by performing DNase/RNase digest tests and gel electrophoresis experiments. Most importantly, P3 exhibited minimum phototoxicity and high photobleaching resistance in cellular medium under continuous exposure to a light source, which are highly desirable for real time monitoring of many biological events. Altogether, the investigated properties of P3 shed light on its admirable and persuasive standing as a cell-compatible, bright and photostable molecular probe for nuclear imaging in various bio-medical applications.