136831-13-5

Basic information

• Product Name: 1H-Indole-2-carboxylic acid, 4-Methyl-, Methyl ester
• Synonyms: 1H-Indole-2-carboxylic acid, 4-Methyl-, Methyl ester;methyl 4-methylindole-2-carboxylate
• CAS NO: 136831-13-5
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.21054
• Mol File: 136831-13-5.mol

Chemical Properties

• Boiling Point: 344.1±22.0 °C(Predicted)
• Appearance: /
• Density: 1.212±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.33±0.30(Predicted)
• CAS DataBase Reference: 1H-Indole-2-carboxylic acid, 4-Methyl-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylic acid, 4-Methyl-, Methyl ester(136831-13-5)
• EPA Substance Registry System: 1H-Indole-2-carboxylic acid, 4-Methyl-, Methyl ester(136831-13-5)

Safety Data

• Hazardous Substances Data: 136831-13-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-2-carboxylic acid, 4-methyl-, methyl ester is used as a building block and intermediate for the synthesis of drugs targeting various medical conditions. Its unique chemical structure and properties make it a promising candidate for drug discovery and development.
Used in Agrochemical Industry:
In the agrochemical industry, 1H-Indole-2-carboxylic acid, 4-methyl-, methyl ester is utilized as an ingredient in the formulation of pesticides and herbicides. Its potential applications in this field contribute to the development of more effective and targeted agricultural chemicals.
Used in Organic Chemistry Research:
1H-Indole-2-carboxylic acid, 4-methyl-, methyl ester is of interest to researchers and chemists in the field of organic chemistry due to its versatile nature and potential applications in the synthesis of various organic compounds. Its unique properties make it a valuable tool for exploring new chemical reactions and developing novel compounds with diverse applications.

Upstream product

• 67-56-1 methanol 
• 18474-57-2 4-methyl-1H-indole-2-carboxylic acid 
• 529-20-4 2-methylphenyl aldehyde 
• 136831-12-4 C₁₁H₁₁N₃O₂ 
• 41085-43-2 2-bromo-3-nitrotoluene 
• 108-44-1 1-amino-3-methylbenzene 
• 126689-79-0 methyl 2-(m-tolylamino)acetate 
• 888723-75-9 3-dimethylamino-2-m-tolylamino-acrylic acid methyl ester 

Downstream Products

• 691362-81-9 methyl 3-formyl-4-methylindole-2-carboxylate 
• 18474-57-2 4-methyl-1H-indole-2-carboxylic acid 
• 1362861-12-8 methyl 3-(2,5-bis(methoxymethoxy)phenyl)-4-methyl-1H-indole-2-carboxylate 

Relevant articles and documents

A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger–Knittel Indole Synthesis

The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.

Synthesis of chromeno[3,4-b]indoles as Lamellarin D analogues: A novel DYRK1A inhibitor class

A library of substituted chromeno[3,4-b]indoles was developed as Lamellarin isosters. Synthesis was achieved from indoles after a four-step pathway sequence involving C-3 iodination, a Suzuki cross-coupling reaction, and a one pot deprotection/lactonisation step. Twenty final compounds were tested in order to determine their activity against topoisomerase I and kinases, the two major biological activities of Lamellarins. One newly synthesized derivative exhibited a strong topoisomerase activity comparable to reference compounds such as campthotecin and Lamellarin with only a weak kinase inhibition. Two other lead compounds were identified as new nanomolar DYRK1A inhibitors and several other drugs affected the kinases in the sub-micromolar range. These results will enable us to use the chromeno[3,4-b]indole as a pharmacophore to develop potent treatments for neurological or oncological disorders in which DYRK1A is fully involved.

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.

Synthesis of the 2,3,4-trisubstituted indole fragments of nosiheptide and glycothiohexide.

Two routes to the protected 4-hydroxymethyl-3-methylindole-2-carboxylate fragment 17 of the thiopeptide antibiotic nosiheptide are described starting from methyl 4-methylindole-2-carboxylate 11, itself prepared in two steps, or from 3-amino-4-chlorobenzoic acid 26. The first route can be adapted to the synthesis of a fragment of the related antibiotic glycothiohexide-alpha, the 3,4-bis(hydroxymethyl)indole-2-carboxylate in which the two hydroxymethyl groups are differentiated as in indole 19 or the lactone 20.

Anti-aids piperazines

The present invention includes diaromatic substituted heterocyclic compounds (III) STR1 which are useful in treating individuals infected with the HIV virus. The invention includes certain previously generically disclosed anti-AIDS piperazinyl compounds (V) and a method of treating HIV infected individuals with the indoles of formula (V) and the anti-AIDS amines (X).