61844-14-2

Basic information

• Product Name: 1H-Indole, 2-(1H-indol-3-ylmethyl)-3-[(4-nitrophenyl)azo]-
• CAS NO: 61844-14-2
• Molecular Formula: C23H17N5O2
• Molecular Weight: 395.42
• Mol File: 61844-14-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 2-(1H-indol-3-ylmethyl)-3-[(4-nitrophenyl)azo]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 2-(1H-indol-3-ylmethyl)-3-[(4-nitrophenyl)azo]-(61844-14-2)
• EPA Substance Registry System: 1H-Indole, 2-(1H-indol-3-ylmethyl)-3-[(4-nitrophenyl)azo]-(61844-14-2)

Safety Data

• Hazardous Substances Data: 61844-14-2(Hazardous Substances Data)

Usage

Aromatic indole ring

The compound contains an indole ring, which is an aromatic structure consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. This imparts stability and aromaticity to the compound.

3-[(4-nitrophenyl)azo]group

This functional group is present in the compound, consisting of a 4-nitrophenyl ring connected to an azo group (N=N). The azo group is responsible for the red coloration of the compound.

Electron-withdrawing nitro group

The nitro group on the 4-nitrophenyl ring is a strong electron-withdrawing group, which can influence the reactivity and properties of the compound in various organic reactions.

Potential applications in organic reactions

Due to the presence of the electron-withdrawing nitro group, the compound may be useful as a reactant or intermediate in various organic synthesis processes.

Use as a dye

The red coloration of the compound, due to the azo group, may make it suitable for use as a dye in various applications.

Biological activity

The indole ring is a common structural motif in many biologically active natural products, suggesting that this compound may have potential applications in the field of medicinal chemistry or as a precursor to biologically active compounds.

Upstream product

• 22546-09-4 3-((2-methyl-1H-indol-3-yl)methyl)-1H-indole 
• 114657-33-9 1-(indol-3-ylcarbonylmethyl)indole-2,3-dione 
• 114648-67-8 (1H-indol-3-yl)-(1H-indol-2-yl)-methanone 
• 91-56-5 indole-2,3-dione 
• 28755-03-5 3-chloroacetylindole 
• 120-72-9 indole 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 114648-66-7 (1H-indol-3-yl)-(1H-indol-2-yl)-methane 
• 1968-05-4 3,3'-diindolylmethane 

Downstream Products

• 100-01-6 4-nitro-aniline 

Relevant articles and documents

Electrophilic Substitution in Indoles. Part 15. The Reaction between Methylenedi-indoles and p-Nitrobenzenediazonium Fluoroborate.

p-Nitrobenzenediazonium fluoroborate (2 mol equiv.) reacts under aqueous conditions with 3,3'-methylenedi-indole (9a) and N,N-dimethyl-3,3'-methylenedi-indole (9c) to give, in each instance, high yields of the corresponding 3-p-nitrophenylazoindoles (13a) and (13c).When 1 mol equiv. of diazonium salt is used, the methylenedi-indole (9a) gives 1 mol equiv. of the 3-(p-nitrophenylazo)indole (13a) and some methylenedi-indole is recovered.In dry acetonitrile, 3,3'-methylenedi-indol gives, with 1 mol equiv. of diazonium salt, a mixture of 3-(p-nitrophenylazo)indole (13a) (0.45 mol equiv.) and the unstable 3-(p-nitrophenylazo)-2,3'-methylenedi-indole (16a) (0.42 mol equiv.).The latter was also synthesized from indole-2,3-dione and chloroacetylindole via indol-2-yl, indol-3-yl, and 2,3'-methylenedi-indole.Essentially similar results were obtained with N,N-dimethyl-3,3'-methylenedi-indole (9c) and the diazonium salt.The unsymmetrical compounds 3-indol-3-ylmethyl-1,2-dimethylindole (9d) and 3-indol-3-ylmethyl-2-methylindole (9e), with 2 mol equiv. of diazonium salt in aqueous solution, each give high yields of the two possible 3-p-nitrophenylazoindoles.With 1 mol equiv. of the diazonium salt only the 2-methyl-3-p-nitrophenylazo derivatives are obtained, together with 3,3'-methylenedi-indole.In dry acetonitrile, with either 1 or 2 mol equiv. of diazonium salt, the unsymmetrical methylenedi-indoles each give only the 2-methyl-3-p-nitrophenylazoindoles.The displacement of an indolylmethyl residue from methylenedi-indoles by the diazonium salt, and the formation of the azo coupled rearrangement product (16a) provides firm evidence that azo coupling of 3-alkylindoles to give the 2,3-disubstituted indoles proceeds by initial attack at the 3-position followed by rearrangement, rather than by direct substitution at the 2-position.