610-51-5

Basic information

• Product Name: 4-methylacridine
• Synonyms: 4-methylacridine
• CAS NO: 610-51-5
• Molecular Formula: C₁₄H₁₁N
• Molecular Weight: 193.24384
• EINECS: 210-226-3
• Mol File: 610-51-5.mol

Chemical Properties

• Melting Point: 114 °C
• Boiling Point: 361.9 °C at 760 mmHg
• Flash Point: 160 °C
• Appearance: /
• Density: 1.155 g/cm³
• Vapor Pressure: 4.19E-05mmHg at 25°C
• Refractive Index: 1.703
• PKA: 5.61±0.10(Predicted)
• CAS DataBase Reference: 4-methylacridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methylacridine(610-51-5)
• EPA Substance Registry System: 4-methylacridine(610-51-5)

Safety Data

• Hazardous Substances Data: 610-51-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Methylacridine is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs with diverse therapeutic applications.
Used in Dye Industry:
As a component in the production of dyes, 4-methylacridine is used as a colorant in various applications, including textiles, plastics, and printing inks, due to its ability to impart vibrant hues.
Used in Chemical Synthesis:
4-Methylacridine is utilized as a building block in the synthesis of other organic compounds, expanding its use in the chemical industry for creating a range of products.
Used in Medicinal Applications:
4-Methylacridine is studied for its potential as an antitumor agent, where it may be used as a therapeutic compound for treating cancer, and as an antibacterial agent, serving to combat bacterial infections.
Used in Research:
In the scientific community, 4-methylacridine is employed as a research tool to explore its biological properties and potential applications in medicine and other fields, furthering our understanding of its capabilities and limitations.

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

Upstream product

• 76943-54-9 4-methyl-9,10-dihydroacridine 
• 76943-53-8 2,6-dimethylphenyl 2-azidobenzoate 
• 95-53-4 o-toluidine 
• 611-23-4 2-nitrosotoluene 
• 100-52-7 benzaldehyde 
• 253120-55-7 methyl 5-methyl-5,6,7,8-tetrahydroacridine-4-carboxylate 
• 271-58-9 anthranil 
• 1374643-16-9 bis(2-methylphenyl)iodonium trifluoromethanesulfonic acid 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1512859-11-8 C₂₁H₂₀N₂ 
• 446-52-6 2-Fluorobenzaldehyde 
• 1512859-22-1 C₁₄H₁₂FN 
• 1066-45-1 trimethyltin(IV)chloride 
• 602302-56-7 9-bromo-4-methylacridine 

Downstream Products

• 578-95-0 10H-acridin-9-one 
• 113139-12-1 N'-(1-acridinylmethylidene)-4-dimethylaminoaniline N'-oxide 

Relevant articles and documents

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.

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.

Preparation method of multi-functional group acridine compound and derivative thereof

The present invention relates to a preparation method of a multi-functional group acridine compound and a derivative thereof. According to the present invention, specifically a bisphosphine ligand and palladium complex catalyzed series connection coupling/cyclization reaction is used to prepare the acridine compound represented by a formula I, wherein various groups are defined in the specification; and the method has advantages of mild reaction condition, simple operation and wide substrate applicability, and the multi-functional group acridine compound and the derivative thereof can be prepared in the high yield manner. The formula I is defined in the specification.

Facile synthesis of acridines via Pd(0)-diphosphine complex-catalyzed tandem coupling/cyclization protocol

A facile and efficient approach for the synthesis of a variety of acridines via the tandem coupling/cyclization of substituted 2-bromobenzaldehydes and anilines is described. The reaction can be accomplished with ease in the presence of a catalytic amount of Pd2(dba)3 and diphosphine ligand dppf, providing a broad range of substituted acridines in good to excellent yields (up to 99%). The Lewis acid, AlCl3, is required to promote the cyclization for less electron-rich anilines.

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.

Chiral 1,8-Diarylnaphthalenes, Methods of Making Them, and Their Use as Sensors

One aspect of the invention relates to 1,8-diarylnaphthalene compounds. In certain embodiments, a compound of the invention is an N-oxide of a 1,8-diarylnaphthalene. In certain embodiments, the aryl group is an optionally substituted acridyl group. In certain embodiments, a compound of the invention is a single steroisomer. In certain embodiments, a compound of the invention is a single enantiomer. Another aspect of the present invention relates to a method of detecting the presence of an analyte in a sample by monitoring the fluorescence of a compound of the invention in a sample. In certain embodiments, the analyte is a metal ion. Another aspect of the present invention relates to a method of determining the enantiomeric purity of an analyte by monitoring the fluorescence of a compound of the invention in the presence of the analyte. In certain embodiments, the analyte is a compound that is capable of hydrogen bonding.

Synthesis of new bis- and tetra-acridines

A new series of bis- and tetra-acridines has been prepared from 4-(bromo-methyl)acridine; some of them exhibited encouraging in vitro cytotoxic activities against murine cell lines.

A preparation of methyl 2-amino-3-formylbenzoate and its use in Friedlander synthesis

The title compound has been prepared in four steps from methyl isatin-7- carboxylate. Condensations with 1-indanone and analogs gave 11H-indeno[1,2- b]quinoline-6-carboxylic acids, and with cyclohexanones gave acridine-4- carboxylic acids.

Generation and Rearrangement of 4aH-carbazoles

The benzotriazoles (12a-c) bearing ortho-blocked 1-aryl substituents have been decomposed thermally by flash vacuum pyrolysis, and photochemically by irradiation in acetonitrile at 254 nm.The pyrolyses are complex giving mainly mono- and di-methylcarbazoles from (12a), di- and trimethylcarbazoles from (12b), and a tetra- and a penta-methylcarbazole from (12c).All of these products could be formed by generation of 4aH-carbazole intermediates (24) with subsequent thermally-allowed sigmatropic rearrangements (Scheme 6).The photolyses give a different set of products consisting mainly of the cyclopentaquinolines (27a-c) from (12a-c), respectively.These products could be formed from the same 4aH-carbazoles (24) which now undergo photochemical, aza-di-?-methane, rearrangements to give intermediates (29) and hence products (27) (Scheme 7).The 4a-methyl intermediate (29c) is intercepted as the adduct (30) in an extended cycloaddition reaction with acrylonitrile.Key reaction products were synthesized by independent methods.

The Pyrolysis of 2-Azidobenzoates. A New Synthesis of Carbazoles and Other N-Heterocycles

The spray pyrolysis of aryl 2-azidobenzoates yields carbazoles, involving a rearrangement whereby the nitrogen of the product is attached to the aryl 1-carbon, a process involving a spiro 6-membered intermediate.When the aryl ortho-positions were both alkyl substituted the product was ab acridan instead.With an ortho-carboxylate, acridone formation competed with that of carbazole.When the CO-O group of the substrate was replaced by O-CO, CO-S, CO-NPh, or SO2-O the pyrolysis was ineffective.Benzyl 2-azidobenzoates, however, pyrolysed to yield 1-benzyl-2,1-benzisoxazolones by an unprecedented C-O insertion reaction of the intermediate nitrene.