613-15-0

Usage

Uses

Used in Chemical Synthesis:
2-Methylacridine is used as a key intermediate in the synthesis of various organic compounds. Its unique chemical structure allows it to be a valuable building block for the creation of dyes, pharmaceuticals, and agrochemicals, contributing to the development of new and improved products in these industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Methylacridine is used as a starting material for the development of new drugs. Its chemical properties make it suitable for the synthesis of active pharmaceutical ingredients, potentially leading to the discovery of novel therapeutic agents.
Used in Agrochemical Industry:
2-Methylacridine is also utilized in the agrochemical industry for the synthesis of various agrochemicals, such as pesticides and herbicides. Its role as an intermediate allows for the creation of effective and targeted solutions for agricultural challenges.
Used in Dye Industry:
In the dye industry, 2-Methylacridine is employed as a precursor for the production of dyes with specific color properties. Its chemical structure enables the development of dyes with unique characteristics, catering to various applications and industries.
Safety Considerations:

InChI:InChI=1/C14H11N/c1-10-6-7-14-12(8-10)9-11-4-2-3-5-13(11)15-14/h2-9H,1H3

Upstream product

• 79365-09-6 2-methyl-9,10-dihydroacridine 
• 23864-43-9 2-methyl-10H-acridin-9-one 
• 26706-97-8 2-methyl-1,2,3,4-tetrahydroacridine 
• 201215-65-8 bis-(2-amino-5-methyl-phenyl)-phenyl-methane 
• 106-38-7 para-bromotoluene 
• 529-23-7 o-aminobenzaldehyde 
• 62152-50-5 2-(4-methylphenylamino)benzaldehyde 
• 82757-39-9 1-(2,4,6-trimethylphenyl)benzotriazole 
• 98-95-3 nitrobenzene 
• 59303-95-6 N-(p-tolyl)anthranilic acid p-toluenesulfonylhydrazide 
• 35709-40-1 N-(p-tolyl)anthranilic acid hydrazide 
• 49604-73-1 ethyl 2-(4-tolylamino)benzoate 
• 16524-23-5 N-p-tolyl-anthranilic acid 
• 28458-49-3 2-(2’,4’,6’-trimethylanilido)nitrobenzene 

Downstream Products

• 113139-10-9 N'-(3-acridinylmethylidene)-4-dimethylaminoaniline N'-oxide 

Relevant academic research and scientific papers

Radical and ionic mechanisms in rearrangements of o-tolyl aryl ethers and amines initiated by the Grubbs-stoltz reagent, et3SiH/KOtbu

Rearrangements of o-tolyl aryl ethers, amines, and sulfides with the Grubbs-Stoltz reagent (Et3SiH + KOtBu) were recently announced, in which the ethers were converted to o-hydroxydiarylmethanes, while the (o-tol)(Ar)NH amines were transformed into dihydroacridines. Radical mechanisms were proposed, based on prior evidence for triethylsilyl radicals in this reagent system. A detailed computational investigation of the rearrangements of the aryl tolyl ethers now instead supports an anionic Truce-Smiles rearrangement, where the initial benzyl anion can be formed by either of two pathways: (i) direct deprotonation of the tolyl methyl group under basic conditions or (ii) electron transfer to an initially formed benzyl radical. By contrast, the rearrangements of o-tolyl aryl amines depend on the nature of the amine. Secondary amines undergo deprotonation of the N-H followed by a radical rearrangement, to form dihydroacridines, while tertiary amines form both dihydroacridines and diarylmethanes through radical and/or anionic pathways. Overall, this study highlights the competition between the reactive intermediates formed by the Et3SiH/KOtBu system.

Benzylic C?H Functionalisation by [Et3SiH+KOtBu] leads to Radical Rearrangements in o-tolyl Aryl Ethers, Amines and Sulfides

Reaction of Et3SiH+KOtBu with diaryl ethers, sulfides and amines that feature an ortho alkyl group leads to rearrangement products. The rearrangements arise from formation of benzyl radicals, likely formed through hydrogen atom abstraction by triethylsilyl radicals. The rearrangements involve cyclisation of the benzyl radical onto the partner arene, which, from computation, is the rate determining step. In the case of diaryl ethers, Truce-Smiles rearrangements arise from radical cyclisations to form 5-membered rings, but for diarylamines, cyclisations to form dihydroacridines are observed. (Figure presented.).

Cu-catalyzed cascade reaction of isoxazoles with diaryliodonium salts for the synthesis of acridines

A straightforward and efficient synthesis of acridine derivatives via a copper-catalyzed cascade reaction among isoxazoles and diaryliodonium salts is achieved. Various mono-, multi-substituted and 9-substituted acridine derivatives could be obtained in moderate to good yields. The process has gone through tandem double arylation and Friedel-Crafts reactions.

Nitrogen-Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole

A nitrogen-iodine exchange protocol of diaryliodonium salts with sodium azide salt is developed for general construction of significant functional acridines and carbazoles, in which introduction of nitrogen at a late stage was successfully established avoiding heteroatom incompatibility. Inorganic sodium azide served as the sole nitrogen atom source in this transformation. The diversiform functional acridines and carbazoles were comprehensively achieved through annulated diaryliodonium salts, respectively. Notably, Acridine orange (a fluorescent indicator for cell lysosomal dye) and Carprofen (a nonsteroidal anti-inflammatory drug) were efficiently established through this protocol.

Nitrogen anthracene class compound and its synthetic method and application (by machine translation)

The invention discloses a formula (2) shown in nitrogen anthracene class of compound and its synthetic method, high Iodized salt as reaction raw material, in the inorganic nitrogen reagent, additive, water, alkali, under the action of the metal catalyst, in the 80 - 150 °C conditions, reacts in a solvent 12 - 60 hours to obtain various nitrogen anthracene class compounds. The invention by post method of introducing nitrogen atoms, to avoid the early stage in the reaction of the nitrogen heterocyclic to metal catalyst of the reaction conditions such as not compatibility; in addition, high Iodized salt in the full utilization of the two aryl, shows that the method of the invention atom economy. Prepared by the method of the invention can be further applied [...] compound of the fluorescent indicator acridine orange synthesis. (by machine translation)

Rh(III)-catalyzed synthesis of unsymmetrical acridines from aldehydes and azides using transient directing strategy in biomass-derived γ-valerolactone

An Rh(III)-catalyzed synthesis of unsymmetrical acridines from aldehydes and azides through bilateral cyclization process in biomass-derived γ-valerolactone has been developed. The in situ-generated imino directing group (DG) from aldehyde and catalytic a

Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds

The Cu-catalyzed regioselective synthesis of phenazine N-oxides was realized from benzoxadiazoles and diaryliodonium salts. The process was initiated by the electrophilic arylation of benzoxadiazoles with diaryliodonium salts and followed by benzocyclization reactions. The further reduction of N-oxides in situ to phenazine scaffolds and deviation to organic fluorescent materials were readily accomplished.

Rh(III)-Catalyzed bilateral cyclization of aldehydes with nitrosos toward unsymmetrical acridines proceeding with C-H functionalization enabled by a transient directing group

A Rh(iii)-catalyzed bilateral cyclization was developed for the efficient construction of acridines proceeding with C-H functionalization whereby in situ formation and removal of an imino transient directing group in the presence of catalytic amount of BnNH2 are achieved. In this transformation, a sequential Rh(iii)-catalyzed C-H amination, cyclization, and aromatization process was involved.

Tandem arylation/friedel-crafts reactions of o-acylanilines with diaryliodonium salts: A modular synthesis of acridine derivatives

A modular method to synthesize acridine derivatives was developed with o-acylanilines and diaryliodonium salts. The reactions proceeded smoothly under Cu-catalyzed or metal-free reaction conditions at elevated temperature through tandem arylation/Friedel-Crafts reactions.

Facile synthesis of acridine derivatives by ZnCl2-promoted intramolecular cyclization of o -arylaminophenyl schiff bases

A concise and efficient method for the synthesis of a wide range of acridine derivatives and polycyclic aza-aromatic compounds from a ZnCl 2-promoted cyclization reaction of readily available o-arylaminophenyl Schiff base compounds under convenient conditions was developed. Reaction conditions and scope of the new method were examined in detail.