51952-99-9

Basic information

• Product Name: 1H-Pyrrole-2,5-dicarboxaldehyde,3,4-dimethyl-(9CI)
• Synonyms: 1H-Pyrrole-2,5-dicarboxaldehyde,3,4-dimethyl-(9CI)
• CAS NO: 51952-99-9
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.16256
• Product Categories: PYRROLE
• Mol File: 51952-99-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Pyrrole-2,5-dicarboxaldehyde,3,4-dimethyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-2,5-dicarboxaldehyde,3,4-dimethyl-(9CI)(51952-99-9)
• EPA Substance Registry System: 1H-Pyrrole-2,5-dicarboxaldehyde,3,4-dimethyl-(9CI)(51952-99-9)

Safety Data

• Hazardous Substances Data: 51952-99-9(Hazardous Substances Data)

Upstream product

• 88108-53-6 2-cyano-3-(3,4-dimethyl-pyrrol-2-yl)-acrylic acid ethyl ester 
• 85057-78-9 5-ethoxycarbonyl-3,4-dimethylpyrrole-2-carboxylic acid 
• 2199-64-6 ethyl 3,5-dimethyl-4-formyl-1H-pyrrole-2-carboxylate 
• 2199-46-4 2-(ethoxycarbonyl)-3,4,5-trimethylpyrrole 
• 64803-96-9 (Z)-5-azido-3,4-dimethyl-pent-3-en-1-yne 
• 38264-09-4 1-chloro-2,3-dimethyl-2-penten-4-yne 
• 50634-31-6 tert-butyl 3,4,5-dimethylpyrrole-2-carboxylate 
• 3855-78-5 2,3,4-trimethyl-1H-pyrrole 
• 86568-97-0 2-(2-cyano-2-(methoxycarbonyl)vinyl)-5-dichloromethyl-3,4-dimethylpyrrole 
• 59435-00-6 2-(2-cyano-2-(methoxycarbonyl)vinyl)-3,4,5-trimethylpyrrole 
• 117112-74-0 2-(2-cyano-2-(methoxycarbonyl)vinyl)-3,4-dimethyl-1H-pyrrole 
• 938-75-0 3,4-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester 
• 19713-89-4 3,4-dimethylpyrrole-2-carboxaldehyde 
• 822-51-5 3,4-dimethyl-1H-pyrrole 

Relevant articles and documents

Synthesis, structural characterization, aromatic characteristics, and metalation of neo-confused porphyrins, a newly discovered class of porphyrin isomers

Neo-confused porphyrins represent a unique family of porphyrin isomers that retain overall aromatic characteristics by virtue of a 17-atom 18π electron delocalization pathway. These porphyrin analogues have a pyrrolic subunit linked in a 1,3-fashion so that a nitrogen atom is directly connected to a meso-bridging carbon. Pyrrole-3-carbaldehydes were shown to react with sodium hydride and 5-acetoxymethylpyrrole-2-carbaldehydes in DMF to give the crucial neo-confused dipyrrolic dialdehyde intermediates. MacDonald "2 + 2" condensation of the dialdehydes with a dipyrrylmethane afforded a dihydroporphyrinoid, and subsequent oxidation with 0.2% aqueous ferric chloride generated a series of fully conjugated neo-confused porphyrins. Unusual dihydroporphyrin byproducts were also identified. Reaction of neo-confused porphyrins with nickel(II) or palladium(II) acetate in refluxing acetonitrile gave excellent yields of the corresponding organometallic derivatives. Proton NMR spectroscopy demonstrates that the diatropic character of this system is diminished compared to regular porphyrins, although neo-confused porphyrins retain porphyrin-like UV-vis spectra. Protonation led to the sequential formation of mono- and dicationic species. Proton NMR spectra for the dications showed the presence of enhanced diamagnetic ring currents.

New one-step synthesis of 3,4-disubstituted pyrrole-2,5-dicarbaldehydes

A smooth and convenient one-step synthesis of 3,4-disubstituted pyrrole- 2,5-dicarbaldehydes 2 is reported. This reaction involves the condensation of β-substituted pyrrole-2-carboxylic acids with triethyl orthoformate in trifluoroacetic acid to give the title compounds in good yield.

A Convenient General Method for the Synthesis of Pyrrole-2,5-dicarbaldehydes

A new general method for the synthesis of pyrrole-2,5-dicarbaldehyde and its 3-mono- and 3,4-disubstituted derivatives is reported.It involves the intermediate formation of the corresponding 2,5-bis(1,3-benzodithiol-2-yl)pyrroles followed by hydrolysis with HgO-35percent aq.HBF4-DMSO.Pyrrole-2,5-dicarbaldehyde was obtained in overall yields of 43-65percent, whilst that of the derivatives was 32-90percent.Moreover the methylation of the corresponding dithiolic intermediate with further hydrolysis resulted in the formation of 1-methylpyrrole-2,5-dicarbaldehyde in 90percent overall yield.