948-43-6

Basic information

• Product Name: N-Methylacridinium iodide
• CAS NO: 948-43-6
• Molecular Formula: C₁₄H₁₂N*I
• Molecular Weight: 194.2512
• Mol File: 948-43-6.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• CAS DataBase Reference: N-Methylacridinium iodide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylacridinium iodide(948-43-6)
• EPA Substance Registry System: N-Methylacridinium iodide(948-43-6)

Safety Data

• Hazardous Substances Data: 948-43-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-Methylacridinium iodide is used as a catalyst for various organic synthesis reactions, facilitating the formation of desired products and improving the efficiency of chemical processes.
Used in Material Development:
N-Methylacridinium iodide is utilized in the development of new materials, contributing to advancements in fields such as nanotechnology, polymer science, and material engineering.
Used in Pharmaceutical Research:
N-Methylacridinium iodide is employed as a reagent in the synthesis of organic compounds, particularly in the pharmaceutical industry, where it aids in the creation of novel drug candidates and therapeutic agents.
Used as a Fluorescent Probe in Biochemical Research:
N-Methylacridinium iodide is used as a fluorescent probe for detecting DNA and RNA, enabling researchers to study the structure, function, and interactions of these biomolecules with enhanced precision and sensitivity.
Used in Antimicrobial Applications:
Due to its antimicrobial properties, N-Methylacridinium iodide is applied in the development of new antimicrobial agents, potentially offering solutions to combat drug-resistant infections and improve public health.
It is crucial to handle N-Methylacridinium iodide with care, as it may pose risks if ingested, inhaled, or comes into contact with skin and eyes, emphasizing the need for proper safety measures during its use in research and industrial settings.

Upstream product

• 30713-65-6 9-hydroxy-9,10-dihydro-10-methylacridine 
• 260-94-6 acridine 
• 74-88-4 methyl iodide 
• 38559-35-2 3,10-dimethyl-5-deazaisoalloxazine 
• 4217-54-3 9,10-dihydro-10-methylacridine 
• 50741-48-5 3-cyano-1-methylquinolinium iodide 
• 42792-95-0 2-methyl-5-nitroisoquinolin-2-ium iodide 

Downstream Products

• 109000-86-4 9-ethyl-10-methyl-9,10-dihydroacridine 
• 3295-69-0 10,10'-dimethyl-9,10,9',10'-tetrahydro-[9,9']biacridinyl 
• 145995-55-7 (9,10-dihydro-10-methyl-9-acridinyl)diphenylphosphine oxide 
• 1707-03-5 diphenyl-phosphinic acid 
• 1706-90-7 methyl diphenylphosphinate 
• 205589-41-9 9-Benzotriazol-1-yl-10-methyl-9,10-dihydro-acridine 
• 4217-54-3 9,10-dihydro-10-methylacridine 
• 134924-37-1 9-ethoxycarbonylmethyl-9,10-dihydro-10-methylacridine 
• 1539289-76-3 C₁₆H₁₄N₄ 
• 1539289-77-4 C₂₁H₁₇N₃ 

Relevant articles and documents

Direct Arylation of Distal and Proximal C(sp3)-H Bonds of t-Amines with Aryl Diazonium Tetrafluoroborates via Photoredox Catalysis

A visible light-mediated arylation protocol for t-amines has been reported through the coupling of γ- and α-amino alkyl radicals with different aryl diazonium salts using Ru(bpy)3Cl2·6H2O as a photocatalyst. Structurally different 9-aryl-9,10-dihydroacridine, 1-aryl tetrahydroisoquinoline, hexahydropyrrolo[2,1-a]isoquinoline, and hexahydro-2H-pyrido[2,1-a]isoquinoline frameworks with different substitution patterns have been synthesized in good yield using this methodology.

The embedding of fluorescent: N -methyl-9-acridone into a topological new layered aluminophosphate SYSU-2 by one-pot synthesis

A layered aluminophosphate |C14H11NO|2[Al4(HPO4)4F4(H2O)2] (denoted as SYSU-2) with a new topology has been hydrothermally synthesized with N-methyl-9-acridone (NMA) as the organic structure-directing agent. Single-crystal X-ray diffraction analysis reveals that SYSU-2 crystallizes in a triclinic space group P1, with the inorganic sheets stacked in an AA sequence. Hydrogen bonds are responsible for the neutral inorganic-organic layer connection. The layer structure of SYSU-2 is constructed by alternating AlO4F2 octahedra and PO4 tetrahedra. The topological analysis of SYSU-2 indicates an independent topology. The NMA layers are self-assembled with π-π interaction. SYSU-2 crystals show interesting dual-band emission fluorescence properties compared with NMA crystals. Under 406 nm UV irradiation, SYSU-2 crystals emit yellow light with two emission bands at 477 and 566 nm, while NMA crystals emit blue light with only one band at 473 nm. The differences may be derived from the difference of stacking orders and distance of NMA molecule layers between the two crystals

Oxo-Free Hydrocarbon Oxidation by an Iron(III)-Isoporphyrin Complex

Metal-halides that perform proton coupled electron-transfer (PCET) oxidation are an important new class of high-valent oxidant. In investigating metal-dihalides, we reacted [FeIII(Cl)(T(OMe)PP)] (1, T(OMe)PP = meso-tetra(4-methoxyphenyl)porphyrinyl) with (dichloroiodo)benzene. An FeIII-meso-chloro-isoporphyrin complex [FeIII(Cl)2(T(OMe)PP-Cl)] (2) was obtained. 2 was characterized by electronic absorption, 1H NMR, EPR, and X-ray absorption spectroscopies and mass spectrometry with support from computational analyses. 2 was reacted with a series of hydrocarbon substrates. The measured kinetic data exhibited a nonlinear behavior, whereby the oxidation followed a hydrogen-atom-transfer (HAT) PCET mechanism. The meso-chlorine atom was identified as the HAT agent. In one case, a halogenated product was identified by mass spectrometry. Our findings demonstrate that oxo-free hydrocarbon oxidation with heme systems is possible and show the potential for iron-dihalides in oxidative hydrocarbon halogenation.

Uncatalyzed Oxidative C?H Amination of 9,10-Dihydro-9-Heteroanthracenes: A Mechanistic Study

A new method for the one-step C?H amination of xanthene and thioxanthene with sulfonamides is reported, without the need for any metal catalyst. A benzoquinone was employed as a hydride (or two-electron and one-proton) acceptor. Moreover, a previously unknown and uncatalyzed reaction between iminoiodanes and xanthene, thioxanthene and dihydroacridines (9,10-dihydro-9-heteroanthracenes or dihydroheteroanthracenes) is disclosed. The reactions proceed through hydride transfer from the heteroarene substrate to the iminoiodane or benzoquinone, followed by conjugate addition of the sulfonamide to the oxidized heteroaromatic compounds. These findings may have important mechanistic implications for metal-catalyzed C?H amination processes involving nitrene transfer from iminoiodanes to dihydroheteroanthracenes. Due to the weak C?H bond, xanthene is an often-employed substrate in mechanistic studies of C?H amination reactions, which are generally proposed to proceed via metal-catalyzed nitrene insertion, especially for reactions involving nitrene or imido complexes that are less reactive (i.e., less strongly oxidizing). However, these substrates clearly undergo non-catalyzed (proton-coupled) redox coupling with amines, thus providing alternative pathways to the widely assumed metal-catalyzed pathways.

Exogenous-oxidant-free electrochemical oxidative C-H phosphonylation with hydrogen evolution

We herein report a versatile and environmentally friendly electrochemical oxidative C-H phosphonylation protocol. This protocol features a broad substrate scope; not only C(sp2)-H phosphonylation, but also C(sp3)-H phosphonylation is tolerated well under exogenous-oxidant-free and metal catalyst-free electrochemical oxidation conditions.

Synthesis and Properties of Acridine and Acridinium Dye Functionalized Bis(terpyridine) Ruthenium(II) Complexes

We present first principle studies on the rational design of an acridine/N-methylacridinium dye (Acr/MeAcr+) substituted terpyridine ligand to investigate if these chromophores can act as triplet-energy storage units in bis(terpyridine) ruthenium(II) complexes. We studied the influence of the dye form (Acr/MeAcr+) as well as the interconnecting linker unit (none, 4-phenyl, or 5-thien-2-yl) and investigated these aspects by steady-state/time-resolved spectroscopy, cyclic voltammetry, X-ray structure analysis, and DFT calculations.

Frustrated Lewis Pair Mediated 1,2-Hydrocarbation of Alkynes

Frustrated Lewis pair (FLP) chemistry enables a rare example of alkyne 1,2-hydrocarbation with N-methylacridinium salts as the carbon Lewis acid. This 1,2-hydrocarbation process does not proceed through a concerted mechanism as in alkyne syn-hydroboration, or through an intramolecular 1,3-hydride migration as operates in the only other reported alkyne 1,2-hydrocarbation reaction. Instead, in this study, alkyne 1,2-hydrocarbation proceeds by a novel mechanism involving alkyne dehydrocarbation with a carbon Lewis acid based FLP to form the new C?C bond. Subsequently, intermolecular hydride transfer occurs, with the Lewis acid component of the FLP acting as a hydride shuttle that enables alkyne 1,2-hydrocarbation.

Oxidative C-H bond functionalization and ring expansion with TMSCHN2: A copper(I)-catalyzed approach to dibenzoxepines and dibenzoazepines

Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for the pharmaceutical industry and academic research. However, their syntheses are generally rather tedious, requiring several steps that involve a Wagner-Meerwein-type rearrangement under harsh conditions. Herein, we present the first copper(I)-catalyzed oxidative C-H bond functionalization and ring expansion with TMSCHN2 to yield these important derivatives in a facile and straightforward way. Cut a long story short: Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for pharmaceuticals, but their syntheses are generally rather tedious. A copper(I)-catalyzed oxidative C-H bond functionalization and ring expansion sequence with TMSCHN2 has been developed to yield these important derivatives in a facile and straightforward way.

Steric Effects on the Primary Isotope Dependence of Secondary Kinetic Isotope Effects in Hydride Transfer Reactions in Solution: Caused by the Isotopically Different Tunneling Ready State Conformations?

The observed 1° isotope effect on 2° KIEs in H-transfer reactions has recently been explained on the basis of a H-tunneling mechanism that uses the concept that the tunneling of a heavier isotope requires a shorter donor-acceptor distance (DAD) than that of a lighter isotope. The shorter DAD in D-tunneling, as compared to H-tunneling, could bring about significant spatial crowding effect that stiffens the 2° H/D vibrations, thus decreasing the 2° KIE. This leads to a new physical organic research direction that examines how structure affects the 1° isotope dependence of 2° KIEs and how this dependence provides information about the structure of the tunneling ready states (TRSs). The hypothesis is that H- and D-tunneling have TRS structures which have different DADs, and pronounced 1° isotope effect on 2° KIEs should be observed in tunneling systems that are sterically hindered. This paper investigates the hypothesis by determining the 1° isotope effect on α- and β-2° KIEs for hydride transfer reactions from various hydride donors to different carbocationic hydride acceptors in solution. The systems were designed to include the interactions of the steric groups and the targeted 2° H/D's in the TRSs. The results substantiate our hypothesis, and they are not consistent with the traditional model of H-tunneling and 1° /2° H coupled motions that has been widely used to explain the 1° isotope dependence of 2° KIEs in the enzyme-catalyzed H-transfer reactions. The behaviors of the 1° isotope dependence of 2° KIEs in solution are compared to those with alcohol dehydrogenases, and sources of the observed "puzzling" 2° KIE behaviors in these enzymes are discussed using the concept of the isotopically different TRS conformations. (Figure Presented).

N-Methylacridinium Salts: Carbon Lewis Acids in Frustrated Lewis Pairs for σ-Bond Activation and Catalytic Reductions

N-methylacridinium salts are Lewis acids with high hydride ion affinity but low oxophilicity. The cation forms a Lewis adduct with 4-(N,N-dimethylamino)pyridine but a frustrated Lewis pair (FLP) with the weaker base 2,6-lutidine which activates H2, even in the presence of H2O. Anion effects dominate reactivity, with both solubility and rate of H2 cleavage showing marked anion dependency. With the optimal anion, a N-methylacridinium salt catalyzes the reductive transfer hydrogenation and hydrosilylation of aldimines through amine-boranes and silanes, respectively. Furthermore, the same salt is active for the catalytic dehydrosilylation of alcohols (primary, secondary, tertiary, and ArOH) by silanes with no observable over-reduction to the alkanes.