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

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

Uses

Used in Pharmaceutical Industry:
1,2-Dimethylindole-3-carboxylic Acid is used as a building block for the synthesis of various bioactive compounds, which can be further developed into potential drug candidates. Its unique structure allows for the creation of molecules with specific biological activities, making it a valuable component in the development of new medications.
Used in Organic Synthesis:
1,2-Dimethylindole-3-carboxylic Acid is used as an intermediate in the synthesis of more complex organic molecules. Its presence in the molecular structure can influence the reactivity and properties of the final product, making it a useful component in the creation of novel compounds for research and development.
Used in Material Sciences:
1,2-Dimethylindole-3-carboxylic Acid is used in the development of new materials with specific properties, such as improved stability or enhanced reactivity. Its incorporation into the molecular structure of these materials can lead to the creation of innovative products with applications in various industries.

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.

Carboxylation of indoles and pyrroles with CO2 in the presence of dialkylaluminum halides

The Lewis acid-mediated carboxylation of arenes with CO2 has been successfully applied to 1-substituted indoles and pyrroles by using dialkylaluminum chlorides instead of aluminum trihalides. Thus, the carboxylation of 1-methylindoles, 1-benzyl-, and 1-phenylpyrroles proceeds regioselectively with the aid of an equimolar amount of Me2AlCl under CO2 pressure (3.0 MPa) at room temperature to afford the corresponding indole-3-carboxylic acids and pyrrole-2-carboxylic acids in 61-85% yields, while the same treatment of 1,2,5-trimethylpyrrole affords the 3-carboxylic acid in 52% yield.

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

2-(Quinuclidin-3-yl)pyrido[4,3-b]indol-1-ones and isoquinolin-1-ones. Potent conformationally restricted 5-HT3 receptor antagonists

Several series of N-(quinuclidin-3-yl)aryl and heteroaryl-fused pyridones were synthesized and evaluated for 5-HT3 receptor affinity. In the heteroaryl series,2-(quinuclidin-3-yl)tetrahydropyrido[4,3-b]indol-1-one (8a) and the 4,5-alkano-bridge