23999-91-9

Basic information

• Product Name: 1H-Pyrrole-2,4-dicarboxaldehyde
• Synonyms: 2,4-DIFORMYLPYRROLE;pyrrole-2,4-dicarboxaldehyde;Pyrrol-2,4-dicarbaldehyd;1H-pyrrole-2,4-dicarboxaldehyde;Pyrrol-2,4-dicarboxaldehyd;2,4-Pyrroldicarboxaldehyd;pyrrole-2,4-dicarbaldehyde
• CAS NO: 23999-91-9
• Molecular Formula: C6H5NO2
• Molecular Weight: 123.111
• Mol File: 23999-91-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole-2,4-dicarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole-2,4-dicarboxaldehyde(23999-91-9)
• EPA Substance Registry System: 1H-Pyrrole-2,4-dicarboxaldehyde(23999-91-9)

Safety Data

• Hazardous Substances Data: 23999-91-9(Hazardous Substances Data)

Usage

Chemical Class

Pyrrole derivatives

Appearance

Yellow to orange crystalline solid

Odor

Strong and pungent

Common Uses

Reactive intermediate in the synthesis of various organic compounds (pharmaceuticals, dyes, fluorescent probes)

Chemical Reactivity

Can undergo condensation, oxidation, and reduction reactions

Special Properties

Ability to form fluorescent complexes with biomolecules

Safety Precautions

Toxic and potentially harmful if not used properly

Upstream product

• 4885-02-3 Dichloromethyl methyl ether 
• 75866-92-1 N-((1H-pyrrol-2-yl)methylene)-N-methylmethanaminium hydrogen chloride 
• 74023-87-3 pyrrole-2,4-dicarbonitrile 
• 152420-76-3 3,5-dichloro-1H-pyrrole-2,4-dicarboxaldehyde 

Downstream Products

• 896138-55-9 2-((3-methoxy-5-phenyl-2H-pyrrol-2-ylidene)methyl)-3,5-dimethyl-1H-pyrrole 
• 803712-67-6 obatoclax 
• 625-82-1 2,4-dimethyl-1H-pyrrole 

Relevant articles and documents

Chemo- and regioselectivity in the reactions of polyfunctional pyrroles

The chemo- and regioselectivity of the reduction, oxidation and Wittig reaction of polyfunctional pyrroles, containing a variety of reactive centres was investigated. The reaction of 3,5-dichloropyrrole-2,4-dicarboxaldehydes with potassium permanganate leads to regioselective oxidation of the 2-formyl group, while the Wittig reaction with 1 equiv of a triphenylphosphorane produced the 2-alkenyl substituted pyrroles. The chemo- and regioselectivity of the reactions of polyfunctional pyrroles, containing a variety of reactive centres is described. Regioselective reduction, oxidation or Wittig reactions give a range of pyrroles suitable for further synthetic transformations.

Pyrrole chemistry. XXI. Synthetic approaches to cyanopyrroles

The Vilsmeier-Haack reaction with pyrrole and 1-methylpyrrole has been modified to provide a direct synthesis of the corresponding 2-nitriles.Chlorosulfonyl isocyanate may be used to prepare the some compounds, but less satisfactorily.The latter reagent does enable the synthesis of pyrrole-2,4-dicarbonitrile in one step.The dinitrile may be reduced to pyrrole-2,4-dicarboxaldehyde.