47135-83-1

Basic information

• Product Name: Phenanthridine, 6-(4-methylphenyl)-
• CAS NO: 47135-83-1
• Molecular Formula: C20H15N
• Molecular Weight: 269.346
• Mol File: 47135-83-1.mol

Chemical Properties

• CAS DataBase Reference: Phenanthridine, 6-(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenanthridine, 6-(4-methylphenyl)-(47135-83-1)
• EPA Substance Registry System: Phenanthridine, 6-(4-methylphenyl)-(47135-83-1)

Safety Data

• Hazardous Substances Data: 47135-83-1(Hazardous Substances Data)

Upstream product

• 2417-95-0 p-tolyllithium 
• 400820-15-7 2'-fluoro-[1,1'-biphenyl]-2-carbonitrile 
• 3128-77-6 2-isocyanobiphenyl 
• 539-44-6 N-4-methylphenylhydrazine 
• 104-85-8 para-methylbenzonitrile 
• 4688-76-0 2-Biphenylboronic acid 
• 874-60-2 4-methyl-benzoyl chloride 
• 24973-49-7 biphenyl-2-carbonitrile 
• 2052-07-5 2-Bromobiphenyl 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 318-13-8 [1,1'-biphenyl]-2-diazonium tetrafluoroborate 
• 98-59-9 p-toluenesulfonyl chloride 
• 90-41-5 2-phenylaniline 
• 400755-57-9 biphenyl-2-yl-(4-methylbenzylidene)amine 

Downstream Products

• 88313-05-7 5-methyl-6-p-tolyl-phenanthridinium; methyl sulfate 

Relevant articles and documents

Ring-Expansion Strategy for α-Aryl Azahelicene Construction: Building Blocks for Optoelectronic Materials

An acid-mediated rapid synthesis of α-aryl azahelicenes via C-C bond cleavage of helical 9H-fluoren-9-ols is reported. The newly introduced aryl ring and pyridine moieties provide an excellent opportunity to further tune the properties of azahelicences: i.e., photoluminescence. The novel α-aryl azahelicenes showcase high circularly polarized luminescence (CPL) efficiencies (4.5 × 10-3) as well as CPL brightness (BCPL), reaching 7.39 M-1 cm-1, which indicates a potential application as chiral emitters.

Catalyst-free synthesis of phenanthridinesviaelectrochemical coupling of 2-isocyanobiphenyls and amines

Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction ofin situformed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode usingnBu4NBF4as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.

Synthesis of phenanthridines through iodine-supported intramolecular C-H amination and oxidation under visible light

Herein, we report a metal-free and step-economic synthesis of phenanthridines from 2-biarylmethanamines under mild conditions. The reaction involves iodine-supported intramolecular C-H amination and oxidation of 5,6-dihydrophenanthridine under air and benign visible light. The mechanism study reveals that visible light plays a key role in both these steps.

Preparation of phenanthridines from N-(o-arylbenzyl)trifluoromethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin

Treatment of N-(o-arylbenzyl)trifluoromethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin in 1,2-dichloroethane under irradiation with a tungsten lamp, followed by the reaction with tBuOK gave the corresponding 6-arylphenanthridines and 6-unsubstituted phenanthridines in good to moderate yields, respectively. The reaction proceeds through an oxidative cyclization onto the aromatic ring by sulfonamidyl radicals formed from the N-iodosulfonamides. The present reaction is a one-pot method for the preparation of both 6-arylphenanthridines and 6-unsubstituted phenanthridines from N-(o-arylbenzyl)trifluoromethanesulfonamides under transition-metal-free conditions.

Synthesis of phenanthridines by I2-mediated sp3C-H amination

An I2-mediated synthesis of phenanthridinesviaintramolecular sp3C-H amination of readily accessible aniline precursors is reported. The present synthetic process is straightforward and applicable to a broad variety of unprotected ani

MANUFACTURING METHOD OF PHENANTHRIDINE COMPOUND

PROBLEM TO BE SOLVED: To provide a manufacturing method of a phenanthridine compound enhancing manufacturing easiness and reducing manufacturing cost. SOLUTION: There is provided a manufacturing method for mixing an imine compound of the following formula and an iodination agent. R1 is an aliphatic group or an aromatic group, R2 to R9 are H, a halogen atom, a linear or branched alkyl group with 1 to 12 carbon atoms, which may be substituted, an aromatic group which may be substituted, or the like, and may form aromatic or non-aromatic ring by binding each other. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

6-Arylphenanthridines from Aryl o-Biaryl Ketones with 1,1,1,3,3,3-Hexamethyldisilazane and Molecular Iodine

Warming treatment of aryl o-biaryl ketones with 1,1,1,3,3,3-hexamethyldisilazane in the presence of Sc(OTf)3 in toluene, followed by the reaction with molecular iodine and K2CO3 in a mixture of THF and methanol at 60 °C gave the corresponding 6-arylphenanthridines in good to moderate yields. The present reaction is a one-pot method for the preparation of 6-arylphenanthridines from aryl o-biaryl ketones through the cyclization of imino-nitrogen-centered radicals that were generated from N-iodo aryl o-biaryl ketimines formed from the reaction of aryl biaryl ketimines with molecular iodine.

Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines

The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).

Preparation of Phenanthridines from o-Cyanobiaryls via Addition of Organic Lithiums to Nitriles and Imino Radical Cyclization with Iodine

Simple treatment of 2-cyanobiaryls with methyllithium, ethylmagnesium bromide, butyllithium, phenyllithium, p-methylphenyllithium, etc., followed by the reaction with water and then with molecular iodine at 60 °C provided efficiently 6-methyl-, 6-ethyl-, 6-butyl-, 6-phenyl, 6-(p-methylphenyl)phenanthridines, etc., in good yields, respectively. Here, imines formed through the addition of carbanion onto the nitriles reacted with molecular iodine to form N-iodoimines smoothly, and their warming treatment induced the formation of imino radicals that smoothly cyclized onto the aryl group to give 6-alkyl- and 6-arylphenanthridines.

Rapid synthesis of polysubstituted phenanthridines from simple aliphatic/aromatic nitriles and iodo arenes: Via Pd(ii) catalyzed domino C-C/C-C/C-N bond formation

An efficient and straightforward method has been developed for the synthesis of polysubstituted phenanthridines from simple aryl iodides and alkyl/aryl nitriles via the palladium-catalyzed nucleophilic addition of aryl iodides to nitriles followed by casc