Pyrrolo[1,2-a]quinoline

Base Information

• Chemical Name: Pyrrolo[1,2-a]quinoline
• CAS No.: 317-17-9
• Molecular Formula: C12H9N
• Molecular Weight: 167.21
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID60446748
• Nikkaji Number: J149.868A
• Wikidata: Q82265464
• Mol file: 317-17-9.mol

Synonyms:pyrrolo[1,2-a]quinoline;317-17-9;Pyrrolo(1,2-a)quinoline;10H-pyrrolo[1,2-a]quinoline;SCHEMBL1958088;XLIQPEZVRBALDD-UHFFFAOYSA-;DTXSID60446748;InChI=1/C12H9N/c1-2-6-12-10(4-1)7-8-11-5-3-9-13(11)12/h1-9H

Chemical Property of Pyrrolo[1,2-a]quinoline

Chemical Property:

• Melting Point: 108-108.5 °C
• Boiling Point: 264.6±13.0 °C(Predicted)
• PSA: 4.41000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 3.09250
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 167.073499291
• Heavy Atom Count: 13
• Complexity: 190

Purity/Quality:

98%min ^*data from raw suppliers

Pyrrolo[1,2-a]quinoline 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=CC=CN32

Technology Process of Pyrrolo[1,2-a]quinoline

There total 12 articles about Pyrrolo[1,2-a]quinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

1-(2-bromophenyl)-1H-pyrrole (69907-27-3) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → pyrrolo[1,2-a]quinoline (317-17-9)

Guidance literature:

With caesium carbonate; palladium diacetate; triphenylphosphine; In toluene; at 120 ℃;

DOI:10.1021/ol070475w

Reference yield: 92.0%

1-(2-bromophenyl)-1H-pyrrole (69907-27-3) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → pyrrolo[1,2-a]quinoline (317-17-9)

Guidance literature:

With palladium diacetate; caesium carbonate; triphenylphosphine; In toluene; at 120 ℃;

DOI:10.1021/acs.orglett.8b01663

Reference yield: 73.0%

1-[2-(2,2-dibromo-vinyl)-phenyl]-1H-pyrrole (1146543-04-5) → pyrrolo[1,2-a]quinoline (317-17-9)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; water; palladium diacetate; caesium carbonate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In toluene; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo900053b

upstream raw materials:

1-(2-(chloromethyl)phenyl)-1H-pyrrole-2-carbaldehyde

triethyl phosphite

1-(2-ethynylphenyl)-1H-pyrrole

1-(2-bromophenyl)-1H-pyrrole

Refernces

• 1、 Chai, David I.,Lautens, Mark. "Tandem Pd-catalyzed double C-C bond formation: Effect of water". supporting information; experimental part. p. 3054 - 3061. Retrieved 2009/08/07.
• 2、 Kobayashi, Kazuhiro,Takanohashi, Atsushi,Himei, Yasutoshi,Sano, Takehiko,Fukamachi, Shuhei,Morikawa, Osamu,Konishi, Hisatoshi. "A new method for the synthesis of pyrrolo[1,2-a]quinolines based on boron trifluoride-mediated cyclization of 1-(2-oxiranylphenyl)pyrroles". . p. 2717 - 2720. Retrieved 2008/09/19.