90935-74-3

Basic information

• Product Name: 3-Methyl-1H-pyrrole-2,5-dicarbaldehyde
• Synonyms: 3-Methyl-1H-pyrrole-2,5-dicarbaldehyde
• CAS NO: 90935-74-3
• Molecular Formula: C₇H₇NO₂
• Molecular Weight: 137.13598
• Mol File: 90935-74-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 79-80 °C(Solv: hexane (110-54-3))
• Boiling Point: 294.6±40.0 °C(Predicted)
• Appearance: /
• Density: 1.277±0.06 g/cm3(Predicted)
• PKA: 13.70±0.50(Predicted)
• CAS DataBase Reference: 3-Methyl-1H-pyrrole-2,5-dicarbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-1H-pyrrole-2,5-dicarbaldehyde(90935-74-3)
• EPA Substance Registry System: 3-Methyl-1H-pyrrole-2,5-dicarbaldehyde(90935-74-3)

Safety Data

• Hazardous Substances Data: 90935-74-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Canadian Journal of Chemistry, 73, p. 675, 1995 DOI: 10.1139/v95-086

Upstream product

• 616-43-3 3-methylpyrrole 
• 51-17-2 benzoimidazole 
• 117720-09-9 5,10-Bis-dimethylamino-2,7-dimethyl-5H,10H-dipyrrolo[1,2-a;1',2'-d]pyrazine-3,8-dicarbaldehyde 
• 64804-02-0 4-methyl-6H-pyrrolo[1,2-c][1,2,3]triazole 
• 68-12-2 N,N-dimethyl-formamide 
• 74-88-4 methyl iodide 
• 178941-14-5 5-(2-Cyano-2-ethoxycarbonylvinyl)-4-methylpyrrole-2-carbaldehyde 
• 58488-39-4 2,5-bis(1,3-benzodithiol-2-yl)pyrrole 
• 932-82-1 4,5-dibromo-1H-pyrrole-2-carbaldehyde 
• 178941-13-4 2-(2-Cyano-2-ethoxycarbonylvinyl)-3-methylpyrrole 
• 24014-18-4 3-methyl-pyrrole-2-carboxaldehyde 
• 1003-67-4 4-methylpyridine-1-oxide 
• 153850-69-2 2,5-bis(1,3-benzodithiol-2-yl)-3-formylpyrrole 

Downstream Products

• 90935-68-5 all-trans-11,14-imino-retinal 

Relevant articles and documents

Convenient route for the synthesis of 3-substituted and 3,4-disubstituted pyrrole-2,5-dicarbaldehydes

3-Substituted and 3,4-disubstituted pyrrole-2,5-dicarbaldehydes have been obtained by hydrolysis with HgO-35% aq. HBF4-DMSO of the intermediates 4 and 5 prepared by electrophilic substitution reactions on 2,5-bis(1,3-benzodithiol-2-yl)pyrrole.

Synthesis of 5-substituted pyrrole-2-carboxaldehydes. Part I. Generation of formal 5-lithiopyrrole-2-carboxaldehyde equivalents by bromine-lithium exchange of 2-bromo-6-(diisopropylamino)-1-azafulvene derivatives

The first known lithiated 1-azafulvene derivatives, e.g., 8 and 13a, were generated by a low-temperature bromine-lithium exchange procedure with tert-butyllithium.These lithio species show substantial stability at /=-90 deg C because, at these temperatures, the sterically demanding 6-diisopropylamino moiety, unlike the dimethylamino group, completely inhibits nucleophilic addition to C-6.At higher temperatures, the addition of tert-butyllithium to C-6 is significant and it can become the dominant process.The lithio species 8 is a useful formal equivalent of 5-lithiopyrrole-2-carboxaldehyde since, on reaction with electrophilic reagents and subsequent hydrolysis, a wide variety of regiochemically pure 5-substituted pyrrole-2-carboxaldehydes is formed.The 6-dialkylamino-1-azafulvenes described herein exist predominantly or exclusively as the syn conformer in solution at room temperature.This conformational preference is confirmed by a significance NOE effect between H-4 and H-6 in the parent diisopropylamino compound 3f.The origin of the syn conformational preference stems from a substantial contribution of the charge-separated form 16 to the ground state structure of these compounds, a phenomenon that is strongly supported by variable temperature NMR measurements on 2-bromo-6-diisopropylamino-1-azafulvene (3c).Key words: 2-bromo-6-diisopropylamino-1-azafulvenes, stereochemistry, lithiation, pyrolle-2-carboxaldehydes.

LITHIATION OF THE DIMER OF 3-BROMO-6-DIMETHYLAMINO-1-AZAFULVENE. EFFICACIOUS SYNTHESIS OF 4-MONO- AND 4,5-DISUBSTITUTED PYRROLE-2-CARBOXALDEHYDES.

The dimer 1a of 3-bromo-6-dimethylamino-1-azafulvene, is shown to function as a formal equivalent of 4-lithio- or 4,5-dilithiopyrrole-2-carboxaldehyde and consequently it is a progenitor, par excellence, of 4-mono- and 4,5-disubstituted pyrrole-2-carboxaldehydes.