95139-42-7

Basic information

• Product Name: 5-(4-chlorophenyl)-2,3-diphenyl-1H-pyrrole
• Synonyms: 5-(4-chlorophenyl)-2,3-diphenyl-1H-pyrrole
• CAS NO: 95139-42-7
• Molecular Weight: 329.829
• Mol File: 95139-42-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 5-(4-chlorophenyl)-2,3-diphenyl-1H-pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-chlorophenyl)-2,3-diphenyl-1H-pyrrole(95139-42-7)
• EPA Substance Registry System: 5-(4-chlorophenyl)-2,3-diphenyl-1H-pyrrole(95139-42-7)

Safety Data

• Hazardous Substances Data: 95139-42-7(Hazardous Substances Data)

Upstream product

• 99275-56-6 4-(4-chloro-phenyl)-1,2-diphenyl-but-2-ene-1,4-dione 
• 100-46-9 benzylamine 
• 29776-35-0 1-(4-chlorophenyl)-3-phenylprop-2-yn-1-one 
• 501-65-5 diphenyl acetylene 
• 208118-80-3 1-(4-chlorophenyl)ethenylacetamide 
• 451-40-1 phenyl benzyl ketone 
• 182422-09-9 4'-chloroacetophenone carbo-t-butoxyhydrazone 
• 99-91-2 para-chloroacetophenone 
• 16483-98-0 2,3-diphenyl-2H-azirine 
• 104-88-1 4-chlorobenzaldehyde 
• 536-74-3 phenylacetylene 

Relevant articles and documents

Base-Mediated Direct Transformation of N-Propargylamines into 2,3,5-Trisubstituted 1 H-Pyrroles

An efficient and base-mediated intramolecular cyclization of N-propargylamines for the synthesis of structurally diversified pyrroles in high yield has been described. The developed methodology is broadly applicable and is tolerated by a variety of functional groups. Key intermediates of natural product discoipyrrole C as well as HMG-CoA-reductase inhibitor have been successfully synthesized using developed chemistry. The proposed mechanism was supported by control experiments.

Iron-Catalyzed Radical Cycloaddition of 2H-Azirines and Enamides for the Synthesis of Pyrroles

A novel and efficient Fe-catalyzed radical cycloaddition of 2H-azirines and enamides for the synthesis of substituted pyrroles has been developed. The radical cycloaddition reaction proceeded through a conceptually new Fe(II)-catalyzed homolytic cleavage of C-N bond of 2H-azirines sequential radical cyclization with enamides. The reaction used readily available starting materials, tolerated various functional groups, and afforded valuable triaryl-substituted pyrroles in good to high yields under mild reaction conditions.

Rhodium-Catalyzed Oxidative Cycloaddition of N-tert-Butoxycarbonylhydrazones with Alkynes for the Synthesis of Functionalized Pyrroles via C(sp3)–H Bond Functionalization

A rhodium(III)-catalyzed cycloaddition of N-tert-butoxycarbonylhydrazones with internal alkynes was developed. The reaction features a regioselective α-imino alkyl C(sp3)?H bond functionalization resulting in selective formation of highly functionalized NH-free pyrroles. Our studies showed that utilizing the N-tert-butoxycarbonyl (N-Boc) as the oxidizing directing group is critical for achieving the observed pyrrole formation versus the isoquinoline formation. To account for the pyrrole formation, we hypothesized that a prior tautomerization of the N-Boc-hydrazones to enamines should occur, followed by regioselective C(sp2)–H cleavage to form a putative five-membered rhodacycle. Subsequent coupling of the rhodacycle with the alkynes would afford the pyrrole products. (Figure presented.).