14844-73-6

Basic information

• Product Name: 2,3-DIMETHYL-1H-INDOLE-5-CARBOXYLIC ACID
• Synonyms: AURORA 6423;CHEMBRDG-BB 4400276;AKOS BBS-00006707;2,3-DIMETHYL-1H-INDOLE-5-CARBOXYLIC ACID;OTAVA-BB BB7111550327;ZERENEX E/5046008;2,3-Dimethyl-1H-indole-5-carboxylic acid 97%;2,3-dimethyl-1H-indole-5-carboxylic acid(SALTDATA: FREE)
• CAS NO: 14844-73-6
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Mol File: 14844-73-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 239-241.5
• Boiling Point: 424.6 °C at 760 mmHg
• Flash Point: 210.6 °C
• Appearance: /
• Density: 1.287 g/cm³
• Vapor Pressure: 5.77E-08mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 4.52±0.30(Predicted)
• CAS DataBase Reference: 2,3-DIMETHYL-1H-INDOLE-5-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHYL-1H-INDOLE-5-CARBOXYLIC ACID(14844-73-6)
• EPA Substance Registry System: 2,3-DIMETHYL-1H-INDOLE-5-CARBOXYLIC ACID(14844-73-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 14844-73-6(Hazardous Substances Data)

Usage

General Description

2,3-Dimethyl-1H-indole-5-carboxylic acid is a chemical compound categorized under the group of indole carboxylic acids. It is also identified by other synonyms such as 5-Carboxy-2,3-dimethyl-1H-indole and 3AI-0532. This organic compound appears as a crystalline solid, often white or slightly yellow in color. The specific applications of this compound are not limited but can be broadly used in research and development laboratories, particularly in the field of synthetic chemistry due to its structural features. It's molecular formula is C11H11NO2 and has a molecular weight of 189.21 g/mol. As with many other chemicals, proper handling and storage are essential to ensure safety and maintain its stability.

InChI:InChI=1/C11H11NO2/c1-6-7(2)12-10-4-3-8(11(13)14)5-9(6)10/h3-5,12H,1-2H3,(H,13,14)/p-1

Upstream product

• 95253-14-8 4-sec-butylidenehydrazino-benzoic acid 
• 619-67-0 4-Hydrazinobenzoic acid 
• 78-93-3 butanone 
• 21523-62-6 2,3-dimethylindole-5-carboxylic acid ethyl ester 

Downstream Products

• 21987-27-9 2,3-dimethyl-1H-indole-5-carboxylic acid methyl ester 
• 1415323-20-4 1-(4-(1-(methoxycarbonyl)cyclopropyl)benzyl)-2,3-dimethyl-1H-indole-5-carboxylic acid 
• 1415321-40-2 (S)-1-(4-((5-((1-(3-isopropylphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)phenyl)cyclopropanecarboxylic acid 
• 1415323-21-5 methyl (S)-1-(4-((5-((1-(3-bromophenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)phenyl)cyclopropanecarboxylate 
• 1415323-22-6 methyl (S)-1-(4-((5-((1-(3-isopropylphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)phenyl)cyclopropanecarboxylate 
• 1428342-78-2 methyl (S)-1-(4-((2,3-dimethyl-5-((1-(3-(prop-1-en-2-yl)phenyl)ethyl)carbamoyl)-1H-indol-1-yl)methyl)phenyl)cyclopropanecarboxylate 
• 1415253-92-7 (S)-4'-((5-((1-(3-isopropylphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid 
• 1415253-93-8 (S)-4'-((5-((1-(3-(tert-butyl)phenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid 
• 1415254-35-1 (S)-4'-((2,3-dimethyl-5-((1-(4-methylphenyl)ethyl)carbamoyl)-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid 
• 1415255-09-2 (S)-4'-((5-((1-(4-ethoxyphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid 
• 1415254-19-1 (S)-4'-((5-((1-(4-isopropylphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid 
• 1415252-61-7 (S)-4'-((5-((1-(4-(tert-butyl)phenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid 
• 1415256-97-1 (S)-tert-butyl 4'-((5-((1-(3-isopropylphenyl)ethyl)carbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)-[1,1'-biphenyl]-2-carboxylate 
• 1220018-39-2 4'-((5-(benzylcarbamoyl)-2,3-dimethyl-1H-indol-1-yl)methyl)biphenyl-2-carboxylic acid 

Relevant articles and documents

INDOLE COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

Methods of treating polyQ diseases or disorders such as Huntington's Disease are presented. Compounds of formula (I) of the disclosure are capable of binding directly to the polyQ segment of mutated huntingtin. This binding results in at least partial rev

Discovery of carbazole carboxamides as novel RORγt inverse agonists

A novel series of carbazole carboxamides was discovered as potent RORγt inverse agonists using a scaffold hybridization strategy. Structure-activity relationship exploration on the amide linker, carbazole ring and arylsulfone moiety of the hybrid amide 3a led to identification of potent RORγt inverse agonists. Compound 6c was found to have a good RORγt activity with an IC50 of 58.5 nM in FRET assay, and reasonable inhibitory activity in mouse Th17 cell differentiation assay (58.8% inhibition at 0.3 μM). The binding mode of carbazole carboxamides in RORγt ligand binding domain was discussed.

Design, Synthesis, and Biological Evaluation of Indole Biphenylcarboxylic Acids as PPARγ Antagonists

The thiazolidinediones (TZD) typified by rosiglitazone are the only approved therapeutics targeting PPARγ for the treatment of type-2 diabetes (T2DM). Unfortunately, despite robust insulin sensitizing properties, they are accompanied by a number of severe side effects including congestive heart failure, edema, weight gain, and osteoporosis. We recently identified PPARγ antagonists that bind reversibly with high affinity but do not induce transactivation of the receptor, yet they act as insulin sensitizers in mouse models of diabetes (SR1664).1 This Letter details our synthetic exploration around this novel series of PPARγ antagonists based on an N-biphenylmethylindole scaffold. Structure-activity relationship studies led to the identification of compound 46 as a high affinity PPARγ antagonist that exhibits antidiabetic properties following oral administration in diet-induced obese mice.