23999-91-9

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 
• 152420-76-3 3,5-dichloro-1H-pyrrole-2,4-dicarboxaldehyde 
• 74023-87-3 pyrrole-2,4-dicarbonitrile 

Downstream Products

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

Relevant academic research and scientific papers

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.

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.

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.

Pyrrole chemistry. XXII. A "one-pot" synthesis of some 4-acylpyrrole-2-carboxaldehydes from pyrrole

The Vilsmeier-Haack intermediates formed from pyrrole and from 1-methylpyrrole may be acylated under normal Friedel-Crafts conditions.Hydrolytic work-up then gives 4-acylpyrrole-2-carboxaldehydes in good yield.The methoxide/methanol treatment of the 4-trichloroacetylated intermediate leads to methyl 2-formylpyrrole-4-carboxylate.These are all "one-pot" syntheses from pyrrole.The formyl group has been removed from several of the products thus affording some 3-acylpyrroles in two operations.