14255-18-6

Basic information

• Product Name: 2-(2-nitroethenyl)-1H-indole
• CAS NO: 14255-18-6
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.1827
• Mol File: 14255-18-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 406.1°C at 760 mmHg
• Flash Point: 199.4°C
• Density: 1.352g/cm³
• Vapor Pressure: 1.95E-06mmHg at 25°C
• Refractive Index: 1.734
• CAS DataBase Reference: 2-(2-nitroethenyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-nitroethenyl)-1H-indole(14255-18-6)
• EPA Substance Registry System: 2-(2-nitroethenyl)-1H-indole(14255-18-6)

Safety Data

• Hazardous Substances Data: 14255-18-6(Hazardous Substances Data)

Usage

Physical State

Yellow solid.

Usage

Synthesis of various pharmaceuticals, agrochemicals, and dyes.

Optical Properties

Luminescent properties, making it valuable in the production of fluorescent dyes and materials.

Potential Health Benefits

Antioxidative and anti-inflammatory effects, making it a promising target for drug development in the future.

Upstream product

• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 75-52-5 nitromethane 
• 24621-70-3 2-(hydroxymethyl)indole 
• 1477-50-5 Indole-2-carboxylic acid 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 487-89-8 Indole-3-carboxaldehyde 

Downstream Products

• 1306669-86-2 (1S,2S)-2-benzyl-1-(nitromethyl)-1H-pyrrolo[1,2-a]indol-3(2H)-one 
• 1304779-83-6 2-(1-benzyl-2,5-dimethyl-1H-pyrrol-3-yl)-1H-indole 
• 1304779-80-3 2-(1-benzyl-2,5-diphenyl-1H-pyrrol-3-yl)-1H-indole 
• 1304779-89-2 2-(1-benzyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)-1H-indole 
• 1304779-94-9 3-(1-benzyl-2-methyl-5-phenyl-1H-pyrrol-3-yl)-1-(phenylsulfonyl)-1H-indole 
• 1304779-95-0 2-(1-benzyl-2-methyl-5-phenyl-1H-pyrrol-3-yl)-1H-indole 
• 496-42-4 1H-indole-2-ethanamine 

Relevant articles and documents

Au(I)-Catalyzed Pictet-Spengler Reactions All around the Indole Ring

Au(I) complexes catalyze iso-Pictet-Spengler reactions. Ethylamine or methylamine chains were introduced at C2, C4, or the nitrogen atom of the indole ring, and the corresponding substrates were reacted in the presence of aldehydes and catalytic amounts of Au(I) complexes, leading to a variety of polycyclic scaffolds. Selectivity could be achieved in the course of a double iso-Pictet-Spengler reaction involving two successive aldehydes, leading to highly complex molecules.

An Enantio- and Diastereoselective Mannich/Pictet–Spengler Sequence To Form Spiro[piperidine-pyridoindoles] and Application to Library Synthesis

A new tandem strategy based on a Mannich/Pictet–Spengler sequence has been developed and applied to the synthesis of a new small library (14 examples) of privileged compounds based on the spiro[piperidine-pyridoindole] core. The sequence proceeds by a diastereoselective Pictet–Spengler cyclization after condensation of several tryptamine derivatives with three novel piperidin-4-ones containing the fluorinated substituents F, CF3and SF5. The piperidin-4-ones were synthesized from readily available starting materials by an enantioselective multi-component organocatalytic Mannich reaction.

One-pot organocatalytic asymmetric synthesis of 1H-pyrrolo[1,2a]indol-3(2H) -ones via a Michael-hemiaminalization-oxidation sequence

An efficient one-pot organocatalytic asymmetric synthesis of 1,2-cis-disubstituted 1H-pyrrolo[1,2a]indol-3(2H)-ones in moderate to good overall yields (49-68%) is presented. The Michael-hemiaminalization-oxidation sequence occurs with very high asymmetric