5412-06-6

Basic information

• Product Name: 5-methylphenanthridinium
• Synonyms: 5-Methylphenanthridinium; phenanthridinium, 5-methyl-
• CAS NO: 5412-06-6
• Molecular Formula: C₁₄H₁₂N
• Molecular Weight: 194.2512
• Mol File: 5412-06-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 5-methylphenanthridinium(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methylphenanthridinium(5412-06-6)
• EPA Substance Registry System: 5-methylphenanthridinium(5412-06-6)

Safety Data

• Hazardous Substances Data: 5412-06-6(Hazardous Substances Data)

Upstream product

• 229-87-8 phenanthridine 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 30319-92-7 5-methyl-5,6-dihydro-phenanthridine 
• 42792-95-0 2-methyl-5-nitroisoquinolin-2-ium iodide 
• 50741-48-5 3-cyano-1-methylquinolinium iodide 
• 38559-35-2 3,10-dimethyl-5-deazaisoalloxazine 
• 2350-75-6 10-methyl-acridinium; bromide 
• 148123-23-3 6-acetonyl-5,6-dihydro-5-methylphenanthridine 
• 7732-18-5 water 
• 10034-85-2 hydrogen iodide 
• 27799-79-7 5,6-dihydrophenanthridine 
• 1015-89-0 6(5H)-phenanthridinone 

Downstream Products

• 30319-92-7 5-methyl-5,6-dihydro-phenanthridine 
• 38559-35-2 3,10-dimethyl-5-deazaisoalloxazine 
• 65201-98-1 5-methylphenanthridinium chloride 

Relevant articles and documents

An unexpected [2+2]-cycloaddition reaction of 4-methyldithieno-[3,4-b:3′,2′-d]pyridinium iodide with dimethyl acetylenedicarboxylate

An unexpected [2+2]-cycloaddition occured in the reaction of 4-methyldithieno-[3,4-b:3′,2′-d]pyridinium iodide (3)with two equivalents of DMAD, giving 4-(trans-1,2-dicarbomethoxy-2- iodovinyl)-5-methyl-6,7-dicarbomethoxy-4,5-dihydrothieno[23-c]quinoline (4) in 54% yield. 4 is formed via 4-methyl-5-(trans-1,2-dicarbomethoxy-2-iodo-4,5-dihydrothieno[3,4-b:3′, 2′-d]pyridine (16), followed by [2+2]-cycloaddition. The primary adduct rearranges via a thiepin to an episulfide which eliminates sulfur to give 4. Copyright

Highly stable phenanthridinium frameworks as a new class of tunable DNA binding agents with cytotoxic properties

A new class of cytotoxic heteroaromatic cations is presented, based on the dihydro-imidazo-phenanthridinium framework (DIP), that have affinity for DNA and cytotoxicity toward cancerous cells. The DIP framework is particularly tunable due to the flexible

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Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones

A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.

Efficient macrocyclization achieved via conformational control using intermolecular noncovalent π-cation/arene interactions

Quinolinium salt 3 is an effective additive that acts as a conformation control element (CCE) to promote macrocyclization to form rigid cyclophanes via olefin metathesis or Glaser-Hay coupling, which do not cyclize in the absence of the additive. The additives are easily synthesized and highly modifiable and have solubility profiles which allow for simple recovery via filtration.