158453-40-8

Basic information

• Product Name: 5-methyl-5H-indolo[2,3-b]quinoline
• Synonyms: 5H-quinindoline, 5-methyl-; Cryptotackieine
• CAS NO: 158453-40-8
• Molecular Formula: C₁₆H₁₂N₂
• Molecular Weight: 232.2799
• Mol File: 158453-40-8.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 393.8°C at 760 mmHg
• Flash Point: 191.9°C
• Density: 1.21g/cm³
• Vapor Pressure: 2.08E-06mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 5-methyl-5H-indolo[2,3-b]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-5H-indolo[2,3-b]quinoline(158453-40-8)
• EPA Substance Registry System: 5-methyl-5H-indolo[2,3-b]quinoline(158453-40-8)

Safety Data

• Hazardous Substances Data: 158453-40-8(Hazardous Substances Data)

Upstream product

• 243-38-9 6H-quinindoline 
• 77-78-1 dimethyl sulfate 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 849-38-7 1,3-bis(2-nitrophenyl)propan-2-one 
• 106653-30-9 1-(quinoline-2-yl)-1H-benzo[d][1,2,3]triazole 
• 1351557-20-4 6-benzyl-6H-indolo[2,3-b]quinoline 
• 3377-71-7 N-benzylindole 
• 6590-65-4 N-(2-Formyl-phenyl)-4-methyl-benzenesulfonamide 
• 1393606-25-1 CF₃O₃S^(1-)*C₁₆H₁₃N₄⁽¹⁺⁾ 
• 104988-73-0 2-(quinolin-3-yl)aniline 
• 615-36-1 2-bromoaniline 
• 197524-30-4 3-(2-azidophenyl)quinoline 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 603-76-9 1-methylindole 

Relevant articles and documents

Synthetic studies towards benzofuro[2,3-b]quinoline and 6H-indolo[2,3-b]quinoline cores: Total synthesis of norneocryptolepine and neocryptolepine

An innovative acid-assisted cascade transformation of indoles with 2-nitrostyrenes was developed, allowing for the one-pot assembly of heterocyclic scaffolds with four fused rings. This strategy was subsequently employed for the concise total synthesis of two natural products, the alkaloids norneocryptolepine and neocryptolepine.

Acid mediated coupling of aliphatic amines and nitrosoarenes to indoles

Traditionally, amines react with nitrosoarenes to provide the corresponding imines or azo compounds. Herein, we report an acid mediated annulation reaction of aliphatic amines and nitrosoarenes to provide indole derivatives. The elusive direct annulation of aliphatic amines and nitrosoarenes via simultaneous C-C and C-N bond formation was achieved under metal free conditions. This conceptually novel method for indole synthesis does not require pre-functionalization steps for the new C-C and C-N bond formation. The method has been applied for an elegant synthesis of nor-neocryptolepine and neocryptolepine.

Palladium-Catalyzed Dual Annulation: A Method for the Synthesis of Norneocryptolepine

A novel procedure for the Pd-catalyzed dual annulation reaction to synthesize the norneocryptolepine derivatives involving the concerted construction of two central heterocycles is reported. The further methylation of the norneocryptolepine to afford its alkaloid analog neocryptolepine implies that synthesis of various neocryptolepine derivatives is feasible. The oxidative addition of Pd(0) is indicated as the key step to activate the intramolecular addition of nitrile according to the mechanism study.