26180-28-9

Basic information

• Product Name: 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid
• Synonyms: 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid;BENZOIC ACID, 3-(2,5-DIMETHYL-1H-PYRROL-1-YL)-;OTAVA-BB 7020618033;UKRORGSYN-BB BBV-158012
• CAS NO: 26180-28-9
• Molecular Formula: C₁₃H₁₃NO₂
• Molecular Weight: 215.25
• Mol File: 26180-28-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 146 °C
• Boiling Point: 401.9 °C at 760 mmHg
• Flash Point: 196.9 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 3.51E-07mmHg at 25°C
• Refractive Index: 1.579
• PKA: 3.71±0.10(Predicted)
• CAS DataBase Reference: 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid(26180-28-9)
• EPA Substance Registry System: 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid(26180-28-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 26180-28-9(Hazardous Substances Data)

Usage

General Description

3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid is a chemical compound that belongs to the pyrrole and benzoic acid groups. Pyrrole is a heterocyclic aromatic organic compound, while benzoic acid is a colorless crystalline solid which is a simple aromatic carboxylic acid. This specific compound is characterized by a pyrrole ring, which is a 5-membered ring with four carbon atoms and one nitrogen atom, with the benzoic acid group attached. The presence of methyl groups on the 2nd and 5th carbon of the pyrrole ring distinguishes this chemical. Detailed information such as its synthesis, potential uses, toxicological data, and physical and chemical properties can be found in scientific literature and databases specific to chemistry and material science.

InChI:InChI=1/C13H13NO2/c1-9-6-7-10(2)14(9)12-5-3-4-11(8-12)13(15)16/h3-8H,1-2H3,(H,15,16)

Upstream product

• 99-05-8 meta-aminobenzoic acid 
• 110-13-4 2,5-hexanedione 

Downstream Products

• 409353-42-0 N-(3-carboxy)phenyl-2,5-dimethyl-3-formylpyrrole 

Relevant articles and documents

A New Green and Efficient Br?nsted: Lewis Acidic DES for Pyrrole Synthesis

Abstract: Deep eutectic solvents (DESs) are fluids composed of different Lewis or Br?nsted acids and bases, generally acknowledged as new analogues to ionic liquids (ILs), because of their similar characteristics, but with more advantages related to preparation cost, environmental impact etc. Their preparation involve the simple mixing of two components generally with moderate heating that are inexpensive, non-toxic, biodegradable and the resulting mixture is capable to overcome the drawbacks of conventional organic solvents and ILs. Chemical reactions with these materials are significantly less hazardous and they can act as catalysts as well as reaction media. Here, three new DESs based on ZrOCl2·8H2O in combination with urea, ethylene glycol and glycerol are introduced. Physicochemical properties like phase behaviour, Freezing point, density, viscosity, thermal stability and miscibility properties in common solvents are determined. In addition, a new method for the determination of acidity of DESs having both Br?nsted and Lewis sites is also introduced in this work. A convenient synthesis of pyrrole through Paal–Knorr reaction is reported using a variety of amines which are used to establish the importance of this catalyst in organic reactions. The products are analysed by GC–MS, 1H NMR and 13C NMR. By comparing the three DESs, DES 1 (formed from ZrOCl2·8H2O with urea) has the lowest density, viscosity, highest acidity and thermal stability. It was shown to be an excellent green catalyst for Paal–Knorr reaction. Reusability of the catalyst was also achieved up to 4 runs, without significant loss in its catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]

Paal-Knorr pyrrole synthesis using recyclable amberlite IR 120 acidic resin: A green approach

Amberlite IR 120 acidic resin, a polymer matrix, has been demonstrated as a catalyst for Paal-Knorr condensation of 2,5-hexadione with primary amines under solvent-free conditions. This is an efficient, mild, and green methodology for N-substituted pyrrole derivatives. Copyright Taylor & Francis Group, LLC.

Design, synthesis, and biological evaluation of N-carboxyphenylpyrrole derivatives as potent HIV fusion inhibitors targeting gp41

On the basis of the structures of small-molecule hits targeting the HIV-1 gp41, N-(4-carboxy-3-hydroxy)phenyl-2,5-dimethylpyrrole (2, NB-2), and N-(3-carboxy-4-chloro)phenylpyrrole (A1, NB-64), 42 N-carboxyphenylpyrrole derivatives in two categories (A and B series) were designed and synthesized. We found that 11 compounds exhibited promising anti-HIV-1 activity at micromolar level and their antiviral activity was correlated with their inhibitory activity on gp41 six-helix bundle formation, suggesting that these compounds block HIV fusion and entry by disrupting gp41 core formation. The structure-activity relationship and molecular docking analysis revealed that the carboxyl group could interact with either Arg579 or Lys574 to form salt bridges and two methyl groups on the pyrrole ring were favorable for interaction with the residues in gp41 pocket. The most active compound, N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrrole (A12), partially occupied the deep hydrophobic pocket, suggesting that enlarging the molecular size of A12 could improve its binding affinity and anti-HIV-1 activity for further development as a small-molecule HIV fusion and entry inhibitor.