53904-16-8

Basic information

• Product Name: indeno[1,2-b]indol-10(5H)-one
• CAS NO: 53904-16-8
• Molecular Formula: C₁₅H₉NO
• Molecular Weight: 219.2381
• Mol File: 53904-16-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 462.6°C at 760 mmHg
• Flash Point: 237.3°C
• Density: 1.394g/cm³
• Vapor Pressure: 9.72E-09mmHg at 25°C
• Refractive Index: 1.783
• CAS DataBase Reference: indeno[1,2-b]indol-10(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: indeno[1,2-b]indol-10(5H)-one(53904-16-8)
• EPA Substance Registry System: indeno[1,2-b]indol-10(5H)-one(53904-16-8)

Safety Data

• Hazardous Substances Data: 53904-16-8(Hazardous Substances Data)

Upstream product

• 1613221-17-2 C₁₉H₁₈BrNO₂ 
• 201230-82-2 carbon monoxide 
• 15224-25-6 3-benzoylindole 
• 1094713-14-0 3-(2-bromobenzoyl)-1H-indole 
• 120-72-9 indole 
• 7154-66-7 2-bromobenzoic acid chloride 
• 1301219-49-7 3-hydroxy-2-(2-nitrophenyl)-1H-inden-1-one 
• 606-23-5 1H-indene-1,3(2H)-dione 
• 609-73-4 o-nitroiodobenzene 
• 53904-15-7 (1H-indol-3-yl)(2-iodophenyl)methanone 
• 123094-92-8 5,10-dihydro-10-trimethylsilylindeno<1,2-b>indole 
• 3254-91-9 5,10-dihydroindeno[1,2-b]indole 
• 40920-46-5 3-chloro-2-phenyl-1-indenone 
• 83-12-5 phenindione 

Downstream Products

• 1422513-17-4 2-(indeno[1,2-b]indol-10(5H)-ylidene)-N-phenylhydrazinecarbothioamide 
• 1422513-12-9 2-(indeno[1,2-b]indol-10(5H)-ylidene)-N-phenylhydrazinecarboxamide 
• 1422512-97-7 10-(2-phenylhydrazono)-5,10-dihydroindeno[1,2-b]indole 

Relevant articles and documents

Divergent synthesis of 6H-isoindolo[2,1-a]indol-6-ones and indenoindolones: An investigation of Pd-catalyzed isocyanide insertion

A novel Pd-catalyzed intramolecular cyclization via tert-butyl isocyanide insertion from 2-(2-bromophenyl)-1H-indoles has been developed, which demonstrates the utility of isocyanides in C-N or C-C bond construction. Treatment of 2-(2-bromophenyl)-1H-indoles with tert-butyl isocyanide affords 6H-isoindolo[2,1-a]indol-6-ones with high efficiency. However, N-methyl or N-Boc protected 2-(2-bromophenyl)-1H-indoles gives indenoindolones in excellent yields under the same condition, which reveals that under the described situation, isocyanides insertion for the formation of C-N bonds is prior to that of C-C bonds.

Pd-Catalyzed Cyclocarbonylation of 2-(2-Bromoaryl)indoles with CO as a C1 Source: Selective Access to 6 H-Isoindolo[2,1-a]indol-6-ones and Indeno[1,2-b]indol-10(5 H)-ones

A highly efficient and regioselective synthetic route to 6 H-isoindolo[2,1-a]indol-6-ones and indeno[1,2-b]indol-10(5 H)-ones through the Pd-catalyzed cyclocarbonylation of 2-(2-bromoaryl)indoles under atmospheric CO pressure has been achieved. Notably, the regioselectivity of the reaction was exclusively dependent on the structural characteristics of the indole substrates. With N-unsubstituted indoles as the starting materials, the reaction afforded 6H-isoindolo[2,1-a]indol-6-ones in good-to-excellent yields. On the other hand, with N-substituted indoles as the substrates, the reaction gave indeno[1,2-b]indol-10(5 H)-ones in a highly regioselective manner.

Friedel-crafts 3-(2-bromobenzoylation) of indoles and intramolecular direct arylation: An efficient route to indenoindolones

An efficient two-step approach, comprising the Friedel-Crafts reaction of 2-bromobenzoyl chlorides with indoles to give 3-(2-bromobenzoyl)indoles and their palladium-catalyzed intramolecular direct arylation to give indenoindolones, has been developed. 3-