317-17-9

Basic information

• Product Name: Pyrrolo[1,2-a]quinoline
• Synonyms: Pyrrolo[1,2-a]quinoline
• CAS NO: 317-17-9
• Molecular Formula: C₁₂H₉N
• Molecular Weight: 167.21
• Mol File: 317-17-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 108-108.5 °C
• Boiling Point: 264.6±13.0 °C(Predicted)
• Appearance: /
• Density: 1.10±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Pyrrolo[1,2-a]quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrrolo[1,2-a]quinoline(317-17-9)
• EPA Substance Registry System: Pyrrolo[1,2-a]quinoline(317-17-9)

Safety Data

• Hazardous Substances Data: 317-17-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 20, p. 1443, 1955 DOI: 10.1021/jo01127a024Tetrahedron, 40, p. 2585, 1984 DOI: 10.1016/S0040-4020(01)96879-6

Upstream product

• 69907-27-3 1-(2-bromophenyl)-1H-pyrrole 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 1001053-74-2 1-(2-oxiranylphenyl)pyrrole 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 615-36-1 2-bromoaniline 
• 1146543-04-5 1-[2-(2,2-dibromo-vinyl)-phenyl]-1H-pyrrole 
• 101130-77-2 1-(2-(chloromethyl)phenyl)-1H-pyrrole 
• 796843-23-7 1-(2-((trimethylsilyl)ethynyl)phenyl)-1H-pyrrole 
• 445262-79-3 1-(2-ethynylphenyl)-1H-pyrrole 
• 101130-78-3 1-(2-(chloromethyl)phenyl)-1H-pyrrole-2-carbaldehyde 
• 122-52-1 triethyl phosphite 

Relevant articles and documents

Synthesis of 1,3-Azaphospholes with Pyrrolo[1,2- a]quinoline Skeleton and Their Optical Applications

A facile synthesis of 1,3-azaphospholes with a pyrrolo[1,2-a]quinoline skeleton has been described. These new annulated 1,3-azaphospholes exhibit good photoelectric performance and can be used as the emitting dopant in organic light-emitting diodes (OLEDs) and dye for bioimaging.

A new method for the synthesis of pyrrolo[1,2-a]quinolines based on boron trifluoride-mediated cyclization of 1-(2-oxiranylphenyl)pyrroles

A simple synthesis of pyrrolo|1,2-a|lquinolines carrying no substituent at all of the 1- to 5-positions based on boron trifluoride-mediated cyclization of 1-(2-oxiranylphenyl)pyrroles, which can be easily prepared from 2-(pyrrol-l- yl)benzatdeh

Synthesis of phenanthrenes and polycyclic heteroarenes by transition-metal catalyzed cycloisomerization reactions

Readily available biphenyl derivatives containing an alkyne unit at one of their ortho-positions are converted into substituted phenanthrenes on exposure to catalytic amounts of either PtCl2, AuCl, AuCl3, GaCl3 or InCl3 in toluene. This 6-endo-dig cyclization likely proceeds through initial π-complexation of the alkyne unit followed by interception of the resulting η2-metal species by the adjacent arene ring. The reaction is inherently modular, allowing for substantial structural variations and for the incorporation of substituents at any site of the phenanthrene product. Moreover, it is readily extended to the heterocyclic series as exemplified by the preparation of benzoindoles, benzocarbazoles, naphthothiophenes, as well as bridgehead nitrogen heterocycles such as pyrrolo[1,2-a]quinolines. Depending on the chosen catalyst, biaryls bearing halo-alkyne units can either be converted into the corresponding 10-halo-phenanthrenes or into the isomeric 9-halo-phenanthrenes; in the latter case, the concomitant 1,2-halide shift is best explained by assuming a metal vinylidene species as the reactive intermediate. The scope of this novel method for the preparation of polycyclic arenes is illustrated by the total synthesis of a series of polyoxygenated phenanthrenes that are close relatives of the anticancer agent combretastatin A-4, as well as by the total synthesis of the aporphine alkaloid O-methyl-dehydroisopiline and its naturally occurring symmetrical dimer.