276239-48-6

Basic information

• Product Name: 4-phenyl-1H-pyrrole-2-carbaldehyde
• Synonyms: 4-phenyl-1H-pyrrole-2-carbaldehyde
• CAS NO: 276239-48-6
• Molecular Weight: 171.199
• Mol File: 276239-48-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-phenyl-1H-pyrrole-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-phenyl-1H-pyrrole-2-carbaldehyde(276239-48-6)
• EPA Substance Registry System: 4-phenyl-1H-pyrrole-2-carbaldehyde(276239-48-6)

Safety Data

• Hazardous Substances Data: 276239-48-6(Hazardous Substances Data)

Upstream product

• 405219-17-2 1-diethoxymethyl-4-iodo-1H-pyrrole-2-carbaldehyde 
• 98-80-6 phenylboronic acid 
• 931-33-9 4-bromopyrrole-2-carboxaldehyde 
• 1003-29-8 2-pyrrole aldehyde 

Downstream Products

• 276239-49-7 4-phenyl-2-formyl-1-(tert-butoxycarbonyl)pyrrole 

Relevant articles and documents

Oxidative Ring-Opening of 1H-Pyrazol-5-amines and Its Application in Constructing Pyrazolo–Pyrrolo–Pyrazine Scaffolds by Domino Cyclization

Herein, an oxidative ring-opening of 1H-pyrazol-5-amines to form 3-diazenylacrylonitrile derivatives under mild and transition-metal-free conditions is described. In addition, the nucleophilic addition of deprotonated 1H-pyrrole-2-carbaldehydes to the vinyl moiety of the yielded 3-diazenylacrylonitriles could trigger domino cyclization to afford the 3H-pyrazolo[3,4-e]pyrrolo[1,2-a]pyrazine derivatives. Computational studies suggest that the oxidation of 1H-pyrazol-5-amines in the presence of PhIO is through the formation of a hydroxylamine intermediate followed by elimination of H2O to result in the ring-opening product. The detailed domino cyclization pathway leading to the pyrazolo–pyrrolo–pyrazine scaffolds is revealed.

Probing the hydrolytic reactivity of 2-difluoromethyl pyrroles

α-Difluoromethyl pyrroles were found to be stable while N-protected with an electron-withdrawing group. Due to the propensity of pyrroles to access azafulvenium-like intermediates, the C-F bonds of an α-difluoromethyl substituent are labile under hydrolytic conditions. The presence of certain electron-withdrawing substituents about the pyrrolic ring can accelerate this process, as determined through a kinetic comparison of the deprotection and subsequent hydrolysis reactions of N-protected β-aryl α-difluoromethyl pyrroles.

Traceless linking of pyrroles: General methology and solid phase supported functionalizations

Transacetalization reaction of the diethoxymethyl (DEM) protected pyrroles 2a-f with the diol functionalized resin 3 resulted in the formation of the immobilized pyrroles 4a-f. Regioselective transformations including Pd-catalyzed coupling reactions and reductive aminations on solid phase were demonstrated.