613-15-0

Basic information

• Product Name: 2-METHYLACRIDINE
• Synonyms: 2-METHYLACRIDINE
• CAS NO: 613-15-0
• Molecular Formula: C₁₄H₁₁N
• Molecular Weight: 193.24
• EINECS: 210-331-4
• Mol File: 613-15-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 361.9°Cat760mmHg
• Flash Point: 160°C
• Appearance: /
• Density: 1.155g/cm³
• Vapor Pressure: 4.19E-05mmHg at 25°C
• Refractive Index: 1.703
• CAS DataBase Reference: 2-METHYLACRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLACRIDINE(613-15-0)
• EPA Substance Registry System: 2-METHYLACRIDINE(613-15-0)

Safety Data

• Hazardous Substances Data: 613-15-0(Hazardous Substances Data)

Usage

General Description

2-Methylacridine is a chemical compound with the molecular formula C13H9N. It is a derivative of acridine and exists as a yellow to brown crystalline solid. 2-Methylacridine is used in the synthesis of various organic compounds, including dyes, pharmaceuticals, and agrochemicals. It is also used as an intermediate in the production of other chemicals. 2-Methylacridine is considered to be a hazardous substance and may cause irritation to the skin, eyes, and respiratory system. It should be handled with caution and appropriate safety measures.

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

• 26706-97-8 2-methyl-1,2,3,4-tetrahydroacridine 
• 106-38-7 para-bromotoluene 
• 529-23-7 o-aminobenzaldehyde 
• 552-89-6 2-nitro-benzaldehyde 
• 123726-16-9 bis(4-methylphenyl)iodonium trifluoromethanesulfonate 
• 615-42-9 1,2-Diiodobenzene 
• 620-23-5 m-tolyl aldehyde 
• 34160-14-0 N-(4-methylphenyl)-2-methylaniline 
• 5720-05-8 4-methylphenylboronic acid 
• 95-53-4 o-toluidine 
• 79365-09-6 2-methyl-9,10-dihydroacridine 
• 271-58-9 anthranil 
• 1512859-09-4 C₂₄H₂₆N₂ 
• 1048657-86-8 C₂₂H₂₂N₂ 

Downstream Products

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

Relevant articles and documents

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.

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.

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.