2-Phenylbenzo[cd]indole

Base Information

• Chemical Name: 2-Phenylbenzo[cd]indole
• CAS No.: 40484-48-8
• Molecular Formula: C₁₇H₁₁N
• Molecular Weight: 229.281
• NSC Number: 144435
• DSSTox Substance ID: DTXSID90301573
• Wikidata: Q82045681
• Mol file: 40484-48-8.mol

Synonyms:40484-48-8;2-phenylbenzo[cd]indole;NSC 144435;NSC144435;DTXSID90301573;NSC-144435

Chemical Property of 2-Phenylbenzo[cd]indole

Chemical Property:

• Vapor Pressure: 1.09E-05mmHg at 25°C
• Boiling Point: 381.8±15.0 °C(Predicted)
• Density: 1.16±0.1 g/cm3(Predicted)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 229.089149355
• Heavy Atom Count: 18
• Complexity: 340

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC3=CC=CC4=C3C2=CC=C4

Technology Process of 2-Phenylbenzo[cd]indole

There total 9 articles about 2-Phenylbenzo[cd]indole 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: 66.0%

N-(8-benzoylnaphthalen-1-yl)picolinamide → 2-phenylbenzo[cd]indole (40484-48-8)

Guidance literature:

With sodium hydroxide; In ethanol; at 80 ℃; for 12h;

DOI:10.1021/acs.orglett.9b00283

Reference yield:

4-methyl-N-(2-(phenylethynyl)-3-(propa-1,2-dien-1-yl)phenyl)benzenesulfonamide → 2-phenylbenzo[cd]indole (40484-48-8) + 2-phenyl-4-(propa-1,2-dien-1-yl)-1-tosyl-1H-indole

Guidance literature:

With (2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)Au(1H-benzotriazole)NTf₂; isopropyl alcohol; silver(I) triflimide; In 1,2-dichloro-ethane; at 60 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.202111267

Reference yield:

2-hydroxy-2-methyl-N-[2-(phenylethynyl)-3-(propa-1,2-dien-1-yl)phenyl]propanamide → 2-phenylbenzo[cd]indole (40484-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1: (2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)Au(1H-benzotriazole)NTf₂ / 1,2-dichloro-ethane / 0.5 h / 60 - 80 °C / Inert atmosphere

2: silica gel

With (2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)Au(1H-benzotriazole)NTf₂; silica gel; In 1,2-dichloro-ethane;

DOI:10.1002/anie.202111267

upstream raw materials:

pyridine-2-carboxylic acid naphthalen-1-ylamide

benzoyl chloride

1-amino-naphthalene

N-(3-bromo-2-(2-phenylethynyl)phenyl)-2-hydroxy-2-methylpropanamide