230291-43-7

Basic information

• Product Name: 1H-Indole-2-carboxylic acid, 4-chloro-, Methyl ester
• Synonyms: 1H-Indole-2-carboxylic acid, 4-chloro-, Methyl ester
• CAS NO: 230291-43-7
• Molecular Formula: C10H8ClNO2
• Molecular Weight: 209.62902
• Mol File: 230291-43-7.mol

Chemical Properties

• Melting Point: 146-147 °C
• Boiling Point: 365.5±22.0 °C(Predicted)
• Appearance: /
• Density: 1.381±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 14.07±0.30(Predicted)
• CAS DataBase Reference: 1H-Indole-2-carboxylic acid, 4-chloro-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylic acid, 4-chloro-, Methyl ester(230291-43-7)
• EPA Substance Registry System: 1H-Indole-2-carboxylic acid, 4-chloro-, Methyl ester(230291-43-7)

Safety Data

• Hazardous Substances Data: 230291-43-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-2-carboxylic acid, 4-chloro-, Methyl ester is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties, including the 4-chloro substituent and the methyl ester functional group, make it a valuable building block for the development of new drugs with diverse therapeutic applications.
Used in Agrochemical Industry:
1H-Indole-2-carboxylic acid, 4-chloro-, Methyl ester is also used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its specific chemical structure allows for the creation of compounds that can effectively control and manage pests and weeds in agricultural settings, contributing to increased crop yields and productivity.
Used in Organic Synthesis:
As a methyl ester, 1H-Indole-2-carboxylic acid, 4-chloro-, Methyl ester can be easily manipulated in organic synthesis reactions, making it a versatile starting material for the production of a wide range of related compounds with diverse chemical properties. This versatility allows researchers and chemists to explore new applications and develop innovative products across various industries.

Upstream product

• 67-56-1 methanol 
• 24621-73-6 4-chloro-1H-indole-2-carboxylic acid 
• 36892-19-0 (2-chloro-6-nitro-phenyl)-pyruvic acid 
• 83-42-1 6-chloro-2-nitrotoluene 
• 108-42-9 3-chloro-aniline 
• 126690-10-6 (3-chloro-phenylamino)-acetic acid methyl ester 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 23967-44-4 4-chloro-1-methyl-1H-indole-2-carboxylic acid 

Relevant articles and documents

3-PHOSPHOGLYCERATE DEHYDROGENASE INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Continuous flow thermolysis of azidoacrylates for the synthesis of heterocycles and pharmaceutical intermediates

An efficient, safe and scalable procedure for the continuous flow thermolysis of azidoacrylates to yield indoles has been developed and was applied to the synthesis of related heterocycles. The scalability of the process was demonstrated in the continuous flow synthesis of a precursor to the DAAO inhibitor 4H-furo[3,2-b]pyrrole-5-carboxylic acid.

[Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation for alkaloid synthesis using aryl azides as nitrogen source

The syntheses of alkaloids including indoles, indolines, tetrahydroquinolines, dihydroquinazolinones and quinazolinones have been accomplished in moderate to excellent yields via [Fe(F20TPP)Cl] catalyzed intramolecular C-N bond formation using aryl azides as nitrogen source.

Rapid and easy access to indoles via microwave-assisted Hemetsberger-Knittel synthesis

Hemetsberger-Knittel indole synthesis can be carried out under microwave activation. The optimum reaction conditions were found by using different solvents and by varying irradiation times and temperature. After 10 min of microwave irradiation, high conversion into the corresponding indole products was achieved without formation of any side products.

Intramolecular C-H amination reactions: Exploitation of the Rh 2(II)-catalyzed decomposition of azidoacrylates

Rhodium(II) perfluorobutyrate-mediated decomposition of vinyl azides provides a new, mild entry into Rh2(II) nitrenoid chemistry. This methodology allows rapid access to a variety of complex, functionalized N-heterocycles in two steps from commercially available starting materials. Copyright

Regioselective and versatile synthesis of indoles via intramolecular Friedel-Crafts heteroannulation of enaminones

A new approach is described for the synthesis of substituted indoles 5, through an intramolecular and regioselective Friedel-Crafts cyclization of enaminones 6a-h catalyzed by Lewis acids. Compounds 6 were prepared from the 2-anilinocarbonyl compounds 7, by treatment with DMFDMA under thermal or microwave (MW) irradiation conditions. An alternative and shorter one-pot two-step synthesis of indoles 5 was achieved starting from compounds 7 and promoted by MW radiation, including the elusive 2-acetylindoles 5i-m. Georg Thieme Verlag Stuttgart.

Probing the subpockets of factor Xa reveals two binding modes for inhibitors based on a 2-carboxyindole scaffold: A study combining structure-activity relationship and X-ray crystallography

Structure-activity relationships within a series of highly potent 2-carboxyindole-based factor Xa inhibitors incorporating a neutral P1 ligand are described with particular emphasis on the structural requirements for addressing subpockets of the factor Xa enzyme. Interactions with the subpockets were probed by systematic substitution of the 2-carboxyindole scaffold, in combination with privileged P1 and P4 substituents. Combining the most favorable substituents at the indole nucleus led to the discovery of a remarkably potent factor Xa inhibitor displaying a Ki value of 0.07 nM. X-ray crystallography of inhibitors bound to factor Xa revealed substituent-dependent switching of the inhibitor binding mode and provided a rationale for the SAR obtained. These results underscore the key role played by the P1 ligand not only in determining the binding affinity of the inhibitor by direct interaction but also in modifying the binding mode of the whole scaffold, resulting in a nonlinear SAR.

Tripeptidyl peptidase inhibitors

The invention is relative to a compound of formula (I) and its use as an inhibitor of the CCK-inactivating peptidase tripeptidyl peptidase (TPP II). The invention concerns in particular the treatment of eating disorder, obesity, psychotic syndrome and associated psychiatric disorders. It concerns also the cosmetic use of a compound (I) in particular to aid slimming.