119673-49-3

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Chlorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications. Its unique structural features allow for the creation of a wide range of structurally diverse compounds, expanding the possibilities for medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(2-Chlorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde serves as an intermediate in the production of various agrochemicals, such as pesticides and herbicides. Its versatility in organic synthesis enables the design of effective compounds targeting specific pests or weeds, contributing to agricultural productivity and crop protection.
Used in Organic Synthesis:
1-(2-Chlorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde is utilized as a versatile building block in organic synthesis, allowing chemists to create a broad spectrum of structurally diverse compounds. Its presence of the chlorophenyl and carbaldehyde groups facilitates the formation of new chemical entities with potential applications in various fields, including materials science and specialty chemicals.
Used in Biological Research:
Due to its potential antimicrobial and anticancer properties, 1-(2-Chlorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde is employed in biological research as a subject of study. Scientists investigate its interactions with biological systems to understand its mechanisms of action and explore its potential as a therapeutic agent in treating infections and cancers.

InChI:InChI=1/C13H12ClNO/c1-9-7-11(8-16)10(2)15(9)13-6-4-3-5-12(13)14/h3-8H,1-2H3

Upstream product

• 110-13-4 2,5-hexanedione 
• 95-51-2 o-chloroaniline 
• 32570-13-1 1-(2-chlorophenyl)-2,5-dimethyl-1H-pyrrole 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 471266-89-4 C₁₈H₁₈ClN₃OS 

Relevant academic research and scientific papers

N-(o-chlorophenyl)-2,5-dimethyl-pyrrole-3-carbaldehyde

Crystal structure analysis of the title compound, C13H12CINO, reveals three crystallographically independent molecules in the asymmetric unit. The main conformational difference between these molecules is the orientation of the phenyl rings with respect to the pyrrole rings. The coplanar arrangement of the aldehyde groups attached to the pyrrole rings influences the pyrrole-ring geometry. The C2-C3 and N1-C5 bonds are noticeably longer than the C4-C5 and N1-C2 bonds. Two independent molecules of the title compound form dimers via intermolecular C-H...O hydrogen bonds [D...A = 3.400 (3) A and D-H...A = 157°]. The perpendicular orientation of the phenyl and pyrrole rings of one independent molecule and its symmetry-related molecule allows C-H...π interactions, with an H...centroid distance of 2.85 A and a C-H...π angle of 155°. The distances between the H atom and the pyrrole-ring atoms indicate that the C-H bond points towards one of the bonds in the pyrrole ring.

Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3- alkyl-2-(alkylimino)thiazolidin-4-one chemotype

High affinity and selective S1P4 receptor (S1P4-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H- pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P4-R agonist hit distinct from literature S1P4-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P4-R agonist activity and exquisite selectivity over the other S1P 1-3,5-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P4-R signaling cascade and elucidate the molecular basis of the receptor function.

Sterically Hindered N-Aryl Pyrroles: Chromatographic Separation of Enantiomers and Barriers to Racemization

The novel N-aryl-2,5-dimethylpyrrole-3-carbaldehydes (1)-(7) have been synthesized by condensation of hexane-2,5-dione with the appropriate aniline and subsequent Vilsmeier-Haack formylation of the pyrrole ring.Diastereoisomeric association complexes of t