27353-44-2

Basic information

• Product Name: 2-chloro-5h-phenanthridin-6-one
• Synonyms: 2-chloro-5h-phenanthridin-6-one;2-chlorophenanthridin-6(5H)-one
• CAS NO: 27353-44-2
• Molecular Formula: C13H8ClNO
• Molecular Weight: 229.66172
• Mol File: 27353-44-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: >260 °C
• Boiling Point: 304.9°C at 760 mmHg
• Flash Point: 138.2°C
• Appearance: /
• Density: 1.346g/cm³
• Vapor Pressure: 0.000847mmHg at 25°C
• Refractive Index: 1.649
• PKA: 12.40±0.20(Predicted)
• CAS DataBase Reference: 2-chloro-5h-phenanthridin-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-5h-phenanthridin-6-one(27353-44-2)
• EPA Substance Registry System: 2-chloro-5h-phenanthridin-6-one(27353-44-2)

Safety Data

• Hazardous Substances Data: 27353-44-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H8ClNO/c14-8-5-6-12-11(7-8)9-3-1-2-4-10(9)13(16)15-12/h1-7H,(H,15,16)

Upstream product

• 1015-89-0 6(5H)-phenanthridinone 
• 319-39-1 N-(p-chlorophenyl)-o-chlorobenzamide 
• 609-65-4 o-chlorobenzoyl chloride 
• 106-47-8 4-chloro-aniline 
• 1238333-76-0 5’-chloro-2’-fluoro-[1,1’-biphenyl]-2-carbonitrile 
• 486-25-9 9-fluorenone 
• 2157-52-0 9-fluorenone oxime 
• 313268-48-3 2-iodo-N-(4-chlorophenyl)benzamide 
• 201230-82-2 carbon monoxide 
• 73006-78-7 5-chloro[1,1'-biphenyl]-2-amine 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 539-03-7 N-(4-chlorophenyl)acetamide 
• 124-38-9 carbon dioxide 
• 873-38-1 4-chloro-2-bromoaniline 

Downstream Products

• 54960-76-8 2-chloro-5-methylphenanthridin-6(5H)-one 
• 1322074-84-9 2-chloro-N-[4-methylphenyl]sulfonyl-5,6-dihydrophenanthridine 
• 1322074-85-0 2-chloro-N-[2-nitrophenyl]sulfonyl-5,6-dihydrophenanthridine 
• 1322074-88-3 2-chloro-4-[(4-methylphenyl)sulfonyl]phenanthridine 
• 1322074-89-4 2-chloro-4-[(2-nitrophenyl)sulfonyl]phenanthridine 
• 38052-81-2 2.6-Dichlor-phenanthridin 

Relevant articles and documents

Photoinduced Annulation of N-Phenylbenzamides for the Synthesis of Phenanthridin-6(5H)-Ones

A general concise method for the synthesis phenanthridin-6(5H)-ones via photoinduced intramolecular annulation of N-phenylbenzamides was developed. Under argon atmosphere and room temperature, phenanthridin-6(5H)-ones were obtained via irradiation N-phenylbenzamides with a 280 nm UV lamp in the presence of methanesulfonic acid in toluene. The mechanism is illustrated and believed to proceed in the order of amides tautomerization, 6π-electric cyclization, [1,5]-H shift, amide-imidine tautomerization, keto-enol tautomerism and evolution hydrogen. (Figure presented.).

Method for synthesizing phenanthridone compound

The invention discloses a method for synthesizing a phenanthridone compound. The method comprises the following steps of: adding an N-hydrocarbon acyloxy amide compound, a transition metal catalyst, acocatalyst and an organic solvent into a reaction container in a nitrogen atmosphere, reacting at 0-40 DEG C for 1-12 hours, and separating and purifying a reaction product to obtain the phenanthridone compound. The method for synthesizing the phenanthridone compound, disclosed by the invention, has the following advantages that: 1, the reaction conditions are mild; 2, less catalyst is used; 3, aligand and an acid-base additive are not needed, the substrate application range is wide, and the method can be compatible with various functional groups such as halogen. 4, the operation is simple;5, the product selectivity is high.

Rhodium(I)-Catalyzed Aryl C-H Carboxylation of 2-Arylanilines with CO2

An unprecedented Rh(I)-catalyzed, amino-group-assisted C-H carboxylation of 2-arylanilines with CO2 under redox-neutral conditions has been developed. This reaction was promoted by a phosphine ligand with t-BuOK as the base and did not require the use of additional strong organometallic reagent. It enabled an efficient direct conversion of a broad range of 2-(hetero)arylanilines including electron-deficient heteroarenes to various phenanthridinones. Possible intermediates of the reaction were also evaluated in the preliminary mechanistic studies.