37395-60-1

Basic information

• Product Name: 2-bromo-5-methylphenanthridin-6(5H)-one
• CAS NO: 37395-60-1
• Molecular Formula: C₁₄H₁₀BrNO
• Molecular Weight: 288.1393
• Mol File: 37395-60-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 455.9°C at 760 mmHg
• Flash Point: 229.5°C
• Density: 1.518g/cm³
• Vapor Pressure: 1.68E-08mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: 2-bromo-5-methylphenanthridin-6(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-bromo-5-methylphenanthridin-6(5H)-one(37395-60-1)
• EPA Substance Registry System: 2-bromo-5-methylphenanthridin-6(5H)-one(37395-60-1)

Safety Data

• Hazardous Substances Data: 37395-60-1(Hazardous Substances Data)

Upstream product

• 94191-66-9 2-bromo-N-methyl-N-phenylbenzamide 
• 100-61-8 N-methylaniline 
• 88-65-3 2-bromobenzoic-acid 
• 4594-73-4 5-methylphenanthridin-6(5H)-one 
• 201230-82-2 carbon monoxide 
• 6911-87-1 4-bromo-N-methylaniline 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 869486-64-6 N-(4-bromo-2-iodophenyl)methylamine 

Relevant articles and documents

Collective Synthesis of Phenanthridinone through C-H Activation Involving a Pd-Catalyzed Aryne Multicomponent Reaction

A palladium-catalyzed multicomponent reaction (MCR) involving aryne, CO, and aniline is established for straightforward assembly of a phenanthridinone scaffold through C-H bond activation. Free combination with multiple kinds of readily available anilines and arynes is facilely achieved for phenanthridinone construction without prefunctionalization. Representative natural products were subsequently synthesized through this MCR strategy highly efficiently. Control experiments and interval NMR tracking revealed the mechanism, particularly the key role of CuF2 in determining the aryne-releasing rate from the precursor in this transformation.

Ligand controlled regiodivergent C1 insertion on arynes for construction of phenanthridinone and acridone alkaloids

A palladium-catalyzed regiodivergent C1 insertion multicomponent reaction involving aryne, CO, and 2-iodoaniline is established to construct the scaffolds of phenanthridinone and acridone alkaloids. Regioselective control is achieved under the guidance of selective ligands. The phenanthridinones are solely obtained under ligand-free condition. In comparison, application of the electron-abundant bidentate ligand dppm afforded the acridones with high efficiency. The release rate of the aryne from the precursor assists the regioselectivity of insertion as well, which was revealed through interval NMR tracking. A plausible mechanism was suggested based on the control experiments. Representative natural products and two types of natural product analogues were synthesized divergently through this tunable method. Divergent alkaloid synthesis: A multicomponent, regioselective approach for palladium-catalyzed C1 insertion is described. This reaction was applied in the divergent synthesis of phenanthridinone and acridone natural product core scaffolds.