131172-61-7

Basic information

• Product Name: 5-(4-CHLORO-PHENYL)-1H-PYRROLE-2-CARBOXYLIC ACID
• Synonyms: 5-(4-CHLORO-PHENYL)-1H-PYRROLE-2-CARBOXYLIC ACID
• CAS NO: 131172-61-7
• Molecular Formula: C₁₁H₈ClNO₂
• Molecular Weight: 221.64
• Mol File: 131172-61-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(4-CHLORO-PHENYL)-1H-PYRROLE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-CHLORO-PHENYL)-1H-PYRROLE-2-CARBOXYLIC ACID(131172-61-7)
• EPA Substance Registry System: 5-(4-CHLORO-PHENYL)-1H-PYRROLE-2-CARBOXYLIC ACID(131172-61-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 131172-61-7(Hazardous Substances Data)

Usage

Derivative

It is derived from pyrrole.

Functional Groups

Carboxylic acid group ( -\textCOOH ): Located at the 2-position of the pyrrole ring.
Chlorophenyl group ( \textC6\textH4\textCl ): Attached to the 5-position of the pyrrole ring.

Potential Applications

Pharmaceutical Industry: Due to its structural features, it may have applications in drug synthesis.

Reactivity

Interesting compound for further research and development in organic chemistry due to its properties and reactivity.

Upstream product

• 91735-77-2 1-(5-(4-chlorophenyl)-1H-pyrrol-2-yl)-2,2,2-trifluoroethan-1-one 
• 153783-24-5 (S)-5-(4-Chloro-phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylic acid ethyl ester 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 153783-19-8 (S)-2-tert-Butoxycarbonylamino-5-(4-chloro-phenyl)-5-oxo-pentanoic acid ethyl ester 
• 1956-39-4 4-chloroacetophenone oxime 
• 19867-89-1 2-(4-chlorophenyl)-1H-pyrrole 
• 99-91-2 para-chloroacetophenone 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 1017414-83-3 5-(4-chlorophenyl)-1-methyl-1H-pyrrole-2-carboxylic acid 

Relevant articles and documents

Synthesis of 5-Arylpyrrole-2-carboxylic Acids as Key Intermediates for NBD Series HIV-1 Entry Inhibitors

5-Arylpyrrole-2-carboxylic acids are important key intermediates in the synthesis of HIV-1 entry inhibitors (such as NBD-11021 and NBD-14010). Here we present a general method for the synthesis of some 5-arylpyrrole-2-carboxylic acids in three steps starting from pyrrole. By this method, the compounds could be prepared on gram scale and without chromatographic purification.

Structure-Based Design of a Small Molecule CD4-Antagonist with Broad Spectrum Anti-HIV-1 Activity

Earlier we reported the discovery and design of NBD-556 and their analogs which demonstrated their potential as HIV-1 entry inhibitors. However, progress in developing these inhibitors has been stymied by their CD4-agonist properties, an unfavorable trait for use as drug. Here, we demonstrate the successful conversion of a full CD4-agonist (NBD-556) through a partial CD4-agonist (NBD-09027), to a full CD4-antagonist (NBD-11021) by structure-based modification of the critical oxalamide midregion, previously thought to be intolerant of modification. NBD-11021 showed unprecedented neutralization breath for this class of inhibitors, with pan-neutralization against a panel of 56 Env-pseudotyped HIV-1 representing diverse subtypes of clinical isolates (IC50 as low as 270 nM). The cocrystal structure of NBD-11021 complexed to a monomeric HIV-1 gp120 core revealed its detail binding characteristics. The study is expected to provide a framework for further development of NBD series as HIV-1 entry inhibitors for clinical application against AIDS.

General method for the synthesis of 5-arylpyrrole-2-carboxylic acids

5-Arylpyrrole-2-carboxylic acids are prepared by DDQ oxidative aromatization of the corresponding ethyl 2-aryl-Δ1-pyrroline-5-carboxylate followed by basic hydrolysis.

SYNTHESIS OF PYRROLE-2-CARBOXYLIC ACIDS AND THEIR N-VINYL DERIVATIVES

Haloform cleavage of 2-trifluoroacetyl- and N-vinyl-2-trifluoroacetylpyrroles gives pyrrole-2-carboxylic acids and their N-vinyl derivatives in good yields; most of these compounds do not melt between 120-190 deg C, but rather decompose with CO2 evolution.