4992-08-9

Basic information

• Product Name: 2-(1H-INDOL-2-YL)BENZOIC ACID
• Synonyms: 2-(1H-INDOL-2-YL)BENZOIC ACID
• CAS NO: 4992-08-9
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.25
• Mol File: 4992-08-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(1H-INDOL-2-YL)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1H-INDOL-2-YL)BENZOIC ACID(4992-08-9)
• EPA Substance Registry System: 2-(1H-INDOL-2-YL)BENZOIC ACID(4992-08-9)

Safety Data

• Hazardous Substances Data: 4992-08-9(Hazardous Substances Data)

Usage

Structure

Derivative of benzoic acid with an indole ring

Potential uses

Anti-inflammatory and anti-cancer agent

Mechanism of action

Inhibits the activity of certain enzymes and proteins involved in inflammation and cancer

Research applications

Building block for the synthesis of various indole-based compounds

Physical properties

White to off-white powder

Solubility

Sparingly soluble in water

Usage

Primarily used in laboratory settings

Upstream product

• 100-63-0 phenylhydrazine 
• 50-78-2 aspirin 
• 69-72-7 salicylic acid 
• 1044518-10-6 methyl 2-[1H-indol-2-yl]benzoate 
• 213318-44-6 N-Boc-indole-2-boronic acid 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 4992-09-0 isoindolo[2,1-a]indol-6-one 

Downstream Products

• 1044518-10-6 methyl 2-[1H-indol-2-yl]benzoate 
• 88207-38-9 3-chloro-2-(2-hydroxymethylphenyl)-1-phenylsulphonylindole 
• 88207-36-7 2-(2-hydroxymethylphenyl)-1-phenylsulphonylindole 
• 88207-41-4 2-(2-tetrahydropyran-2-yloxymethylphenyl)indole 
• 88207-35-6 2-(2-hydroxymethylphenyl)indole 

Relevant articles and documents

Synthesis and molecular docking based exploration of salicylic acid derivatives

In present study, four salicylic acid derivatives viz., 2-acetoxybenzoic acid (2a), 2-(1H-indol-2-yl)benzoic acid (3a), 5-chloro-2-acetoxybenzoic acid (2b) and 5-chloro-2-(1H-indol-2-yl)benzoic acid (3b) were synthesized and studied for molecular docking on 3JUS and 3UPI protein selected from pdb. The studies show that all of the four synthesized compounds were found to be docked. Compound 3a and 3b showed the best ligand pose energy -10.8163 kcal/mol and -11.1354 kcal/mol with docking run: elapsed time 9 s and 12 s, respectively in respect of 3JUS Further, compounds 3a and 3b showed the best ligand pose energy -9.17851 and -9.54722 kcal/mol with docking run: elapsed time 10 and 14 s, respectively in case of 3UPI. Hence, studies showed that 5-chloro-2-(1H-indol-2-yl)benzoic acid (3b) emerged as potent compound which might show diverse nature of biological and therapeutic activity.

Isoindolo[2,1-a]indol-6-one-a new pyrolytic synthesis and some unexpected chemical properties

Isoindolo[2,1-a]indol-6-one 1 is formed by a sigmatropic shift-elimination-cyclisation cascade by flash vacuum pyrolysis (FVP) of methyl 2-(indol-1-yl)benzoate 7 at 950 °C. The dihydro compound 16 is easily obtained by catalytic reduction of 1, but the reaction is very sensitive to steric effects at the 11-position. Attempted ring-opening of 1 in basic methanol provides an equilibrium of isoindolo[2,1-a]indol-6-one 1 and the ester 19. Lithium aluminium hydride reduction of 1 provides the alcohol 22 which can be dehydrated to a mixture of 23 and 24 by FVP at 800-950 °C.

Indole β-Nucleophilic Substitution. Part 7. β-Halogenation of Indoles. Attempted Intramolecular β-Nucleophilic Substitution of α-Arylindoles

Intramolecular β-nucleophilic substitution of 2-aryl-1-phenylsulphonylindoles could not be achieved.N-Arylsulphonylation of 2-arylindoles with arylsulphonyl halides using phase-transfer conditions is accompanied by 3-halogenation in some cases; the propor