20357-15-7

Basic information

• Product Name: 1,2-DIMETHYLINDOLE-3-CARBOXYLIC ACID
• Synonyms: RARECHEM AL BO 1939;TIMTEC-BB SBB010180;ASINEX-REAG BAS 12968454;BUTTPARK 153\33-42;1,2-DIMETHYL-1H-INDOLE-3-CARBOXYLIC ACID;1,2-DIMETHYLINDOLE-3-CARBOXYLIC ACID;3-Carboxy-1,2-dimethyl-1H-indole
• CAS NO: 20357-15-7
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• Product Categories: Indole
• Mol File: 20357-15-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 200-202
• Boiling Point: 393.1 °C at 760 mmHg
• Flash Point: 191.5 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 6.95E-07mmHg at 25°C
• PKA: 4.03±0.10(Predicted)
• CAS DataBase Reference: 1,2-DIMETHYLINDOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DIMETHYLINDOLE-3-CARBOXYLIC ACID(20357-15-7)
• EPA Substance Registry System: 1,2-DIMETHYLINDOLE-3-CARBOXYLIC ACID(20357-15-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 20357-15-7(Hazardous Substances Data)

Usage

General Description

1,2-Dimethylindole-3-carboxylic Acid is a chemical compound that belongs to the class of organic compounds known as indoles, which contain a bicyclic structure of a six-membered benzene ring fused to a five-membered nitrogenous ring. It is specific in structure due to the presence of two methyl groups attached at the first and second positions of the indole nucleus, with a carboxylic acid group at the third position. This chemical is important in various fields of study and application, including pharmaceuticals, organic synthesis, and material sciences. It plays a role in the synthesis of several complex molecules, including some bioactive compounds. Data about its physical and chemical properties, toxicity, and safety handling is usually available from official material safety data sheets.

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

Upstream product

• 72036-47-6 ethyl acetoacetate N-methyl-N-phenylhydrazone 
• 32387-21-6 1-methyl-3-indolecarboxylic acid 
• 74-88-4 methyl iodide 
• 20357-14-6 ethyl 1,2-dimethyl-1H-indole-3-carboxylate 
• 108438-43-3 methyl 1-methyl-1H-indole-3-carboxylate 
• 875-79-6 1,2-dimethylindole 
• 124-38-9 carbon dioxide 

Relevant articles and documents

Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.

VLA-4 INHIBITORS

The present invention relates to a compound represented by the following formula (I): (wherein, W represents WA-A1 -WB - (in which, WA is substituted or unsubstituted aryl, etc., A1 is -NR1-, single bond, -C(O)-, etc., and WB is substituted or unsubstituted arylene, etc.), R is single bond, -NH-, -OCH2-, alkenylene, etc., X is -C(O) -CH2-, etc., and M is, for example, the following formula: (in which, R11, R12 and R13 each independently represents hydrogen, hydroxyl, amino, halogen, etc., R14 is hydrogen or lower alkyl, Y represents -CH2-O-, etc., Z is substituted or unsubstituted arylene, etc., A2 is single bond, etc, and R10 is hydroxyl or lower alkoxy)), or salt thereof; and a medicament containing the same. This compound or salt thereof selectively inhibits binding of cell adhesion molecules to VAL-4 and exhibits high bioavailability so that it is useful as a preventive and/or remedy for inflammatory diseases, autoimmune diseases, metastasis, bronchial asthma, rhinostenosis, diabetes, and the like.

Preparation of 2,3-Disubstituted Indoles from Indole-3-carboxylic Acids and Amides by α-Deprotonation

Direct deprotonations have been used to obtain the 2(α)-lithiated indole-3-carboxylate dianions 8 and 14, together with the related 2(α)-lithiated indole-3-carboxamide monoanions 18 and 20b from the parent compounds.These four intermediates are useful for