3955-65-5

Basic information

• Product Name: 6-METHYLPHENANTHRIDINE
• Synonyms: 6-METHYLPHENANTHRIDINE
• CAS NO: 3955-65-5
• Molecular Formula: C₁₄H₁₁N
• Molecular Weight: 193.24384
• Mol File: 3955-65-5.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 352.5°Cat760mmHg
• Flash Point: 154.8°C
• Appearance: /
• Density: 1.155g/cm³
• Vapor Pressure: 7.75E-05mmHg at 25°C
• Refractive Index: 1.703
• CAS DataBase Reference: 6-METHYLPHENANTHRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHYLPHENANTHRIDINE(3955-65-5)
• EPA Substance Registry System: 6-METHYLPHENANTHRIDINE(3955-65-5)

Safety Data

• Hazardous Substances Data: 3955-65-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 1841, 1974 DOI: 10.1021/jo00927a012

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

Upstream product

• 34456-70-7 [1,2,3]triazolo[1,5-f]phenanthridine 
• 14548-01-7 phenanthridine N-oxide 
• 2181-42-2 trimethylsulphonium iodide 
• 318-13-8 [1,1'-biphenyl]-2-diazonium tetrafluoroborate 
• 70-55-3 toluene-4-sulfonamide 
• 75-05-8 acetonitrile 
• 110-05-4 di-tert-butyl peroxide 
• 3128-77-6 2-isocyanobiphenyl 
• 19433-17-1 acetophenone O-acetyloxime 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1101835-56-6 C₃₀H₂₄N₂O₄ 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 352427-11-3 tert-Butyl [({[2-(phenylsulfonyl)phenyl]ethylidene}amino)oxy]peracetate 
• 146174-68-7 4-t-butylcyclohexyl 6-phenanthridinylmethyl ether 

Downstream Products

• 40484-36-4 6-(chloromethyl)phenanthridine 
• 3900-22-9 6-methylphenanthridine 5-oxide 
• 24160-09-6 6-phenanthridinecarbaldehyde 
• 1015-89-0 phenanthridin-6-ol 
• 19711-96-7 6-methyl-5-tosyl-5,6-dihydrophenanthridine 

Relevant articles and documents

C2-Selective C-H methylation of heterocyclic N-oxides with sulfonium ylides

A redox-neutral C2-selective methylation of heterocyclic N-oxides with sulfonium ylides is described herein. This report presents unprecedented findings for the utility of sulfonium ylides as the methylation source of N-heterocycles beyond the Corey-Chaykovsky reaction. Intriguingly, pyrrolidine plays a significant role in minimizing the reductive C2-methylation process. This method is characterized by its mild conditions, simplicity, and excellent site selectivity. The applicability of the developed protocol is showcased by the late-stage methylation and sequential transformations of complex drug molecules.

Cathode Material Determines Product Selectivity for Electrochemical C?H Functionalization of Biaryl Ketoximes

The synthesis of polycyclic N-heteroaromatic compounds and their corresponding N-oxides has been developed through electrochemical C?H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wide range of N-heteroaromatic N-oxides. The products of the electrosynthesis are switched to the deoxygenated N-heteroaromatics by employing a Pb cathode through sequential anode-promoted dehydrogenative cyclization and cathodic cleavage of the N?O bond in the initially formed N-oxide.

Pd-catalyzed assembly of phenanthridines from aryl ketone O-acetyloximes and arynes through C-H bond activation

Pd-catalyzed annulation of aryne and aryl ketone O-acetyloxime via C-H bond activation was realized. Through the C-H bond activation/insertion/cyclization/ elimination reaction sequence, phenanthridines are successfully constructed, providing an attractiv