5-Methyl-6(5h)-phenanthridinone

Base Information

• Chemical Name: 5-Methyl-6(5h)-phenanthridinone
• CAS No.: 4594-73-4
• Molecular Formula: C14H11NO
• Molecular Weight: 209.247
• Hs Code.: 2933990090
• NSC Number: 141586
• DSSTox Substance ID: DTXSID90301174
• Nikkaji Number: J80.858J
• Wikidata: Q82044816
• ChEMBL ID: CHEMBL1965582
• Mol file: 4594-73-4.mol

Synonyms:4594-73-4;5-methyl-6(5h)-phenanthridinone;6(5H)-Phenanthridinone,5-methyl-(7CI,8CI,9CI);NSC141586;N-methyl-6-phenanthridone;SCHEMBL346785;5-Methyl-6(5H)-phenanthridone;CHEMBL1965582;DTXSID90301174;UWZASNFULUENAC-UHFFFAOYSA-N;NSC-141586;NCI60_000913

Chemical Property of 5-Methyl-6(5h)-phenanthridinone

Chemical Property:

• Vapor Pressure: 1.9E-06mmHg at 25°C
• Refractive Index: 1.635
• Boiling Point: 395.01 °C at 760 mmHg
• Flash Point: 191.547 °C
• PSA: 22.00000
• Density: 1.205 g/cm³
• LogP: 2.69170
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 209.084063974
• Heavy Atom Count: 16
• Complexity: 289

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C3=CC=CC=C3C1=O

Technology Process of 5-Methyl-6(5h)-phenanthridinone

There total 15 articles about 5-Methyl-6(5h)-phenanthridinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 49.0%

carbon monoxide (201230-82-2) + N-methyl-2-iodoaniline (57056-93-6) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → 10-methyl-9, 10-dihydro-9-acridinone (719-54-0) + 5-methylphenanthridin-6(5H)-one (4594-73-4)

Guidance literature:

With palladium diacetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; cesium fluoride; In acetonitrile; at 100 ℃; for 12h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201508340

Reference yield: 49.0%

2-chloro-N-methyl-N-phenylbenzamide (7022-47-1) → 5-methylphenanthridin-6(5H)-one (4594-73-4) + N-methyl-N-phenyl-benzamide (1934-92-5)

Guidance literature:

With potassium tert-butylate; vasicine; In sulfolane; at 120 ℃; for 0.25h; Reagent/catalyst; Solvent; Microwave irradiation; Sealed tube;

DOI:10.1039/c6ob01362g

Reference yield: 40.0%

lithium hydroxytris(pentafluorophenyl)borate + 5-methylphenanthridin-5-ium trifluoromethanesulfonate → N-methylphenanthridinium hydroxytris(pentafluorophenyl)borate + 5-methylphenanthridin-6(5H)-one (4594-73-4)

Guidance literature:

In water; at 20 ℃; for 2h;

DOI:10.1021/jo050695s

upstream raw materials:

2-(N-benzoyl-N-methylamino)benzoic acid

2-Iodo-N-methyl-N-phenylbenzamide

N-methyl-N-phenyl-2-nitrobenzamide

2-amino-N-methyl-N-phenylbenzamide

Downstream raw materials:

2-bromo-5-methylphenanthridin-6(5H)-one

5-methylphenanthridinium chloride

N-methyl-6(5H)-thiophenanthridione

Refernces

• 1、 Sharma, Sushila,Kumar, Manoranjan,Sharma, Shruti,Nayal, Onkar S.,Kumar, Neeraj,Singh, Bikram,Sharma, Upendra. "Microwave assisted synthesis of phenanthridinones and dihydrophenanthridines by vasicine/KO: T Bu promoted intramolecular C-H arylation". . p. 8536 - 8544. Retrieved 2016/09/28.
• 2、 Feng, Minghao,Tang, Bingqing,Wang, Nengzhong,Xu, Hong-Xi,Jiang, Xuefeng. "Ligand controlled regiodivergent C1 insertion on arynes for construction of phenanthridinone and acridone alkaloids". . p. 14960 - 14964. Retrieved 2016/02/05.