208-71-9

Basic information

• Product Name: Pyrrolo[3,2,1-jk]carbazole
• Synonyms: Pyrrolo[3,2,1-jk]carbazole
• CAS NO: 208-71-9
• Molecular Formula: C₁₄H₉N
• Molecular Weight: 191.228
• Mol File: 208-71-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 302.006°C at 760 mmHg
• Flash Point: 136.449°C
• Density: 1.236g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.716
• CAS DataBase Reference: Pyrrolo[3,2,1-jk]carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolo[3,2,1-jk]carbazole(208-71-9)
• EPA Substance Registry System: Pyrrolo[3,2,1-jk]carbazole(208-71-9)

Safety Data

• Hazardous Substances Data: 208-71-9(Hazardous Substances Data)

Upstream product

• 78943-58-5 N-benzyl-5H-dibenzoazepine 
• 74074-19-4 5-allyl-5H-dibenzo[b,f]azepine 

Relevant articles and documents

Thermal Ring Contraction of Dibenz[b,f]azepin-5-yl Radicals: New Routes to Pyrrolo[3,2,1-jk]carbazoles

(Chemical Equation Presented) Flash vacuum pyrolysis (FVP) of N-allyl- or N-benzyldibenz[b,f]azepine at temperatures from 750 to 950°C gives pyrrolo[3,2,1-jk]carbazole as the major product. The mechanism of the ring contraction involves dibenzazepin-1-yl radical formation, followed by transannular attack and formation of a 2-(indol-1-yl)phenyl radical which cyclizes. The mechanism is supported by independent generation of 2-(indol-1-yl)phenyl radicals by two different methods, and the use of 1-(2-nitrophenyl)indole as a radical generator gives an optimized synthetic route to pyrrolo[3,2,1-jk]carbazole (54% overall yield in two steps from indole). The first substituted pyrrolo[3,2,1-jk]carbazoles have been synthesized by FVP methods and also by reactions of the parent compound with electrophiles, leading to a range of 4-substituted pyrrolocarbazoles.