34225-81-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Methylindene-2-carboxylic acid is used as an active pharmaceutical ingredient for its potential therapeutic effects. Its unique chemical structure allows it to interact with biological targets, offering new avenues for the development of drugs to treat various diseases and conditions.
Used in Materials Science:
In the field of materials science, 3-Methylindene-2-carboxylic acid is utilized as a key component in the synthesis of advanced materials. Its properties contribute to the development of materials with specific characteristics, such as improved strength, stability, or functionality, for use in various applications.
Used in Organic Synthesis:
3-Methylindene-2-carboxylic acid serves as a versatile building block in organic synthesis. Its reactivity and structural features enable the creation of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals, expanding the scope of chemical research and innovation.
As the potential uses of 3-Methylindene-2-carboxylic acid continue to be explored, its applications in various industries are expected to grow, further highlighting its importance as a valuable chemical compound.

InChI:InChI=1/C11H10O2/c1-7-9-5-3-2-4-8(9)6-10(7)11(12)13/h2-5H,6H2,1H3,(H,12,13)

Upstream product

• 620-79-1 Ethyl 2-benzylacetoacetate 
• 7664-93-9 sulfuric acid 
• 7316-64-5 3-methylindene-2-carboxylic acid methyl ester 
• 3666-82-8 2-benzyl-3-oxo-butyric acid methyl ester 
• 2382-58-3 2-benzyl-3-oxobutanoic acid 
• 124-38-9 carbon dioxide 
• 767-60-2 3-Methylindene 
• 22433-39-2 1-methyl-1-phenylallene 

Downstream Products

• 103343-92-6 3-Methyl-1H-indene-2-carboxylic acid [5-(2-fluoro-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl]-amide 
• 124-38-9 carbon dioxide 
• 767-59-9 1-Methylinden 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 184102-76-9 3‐methyl‐1H‐indene‐2‐carbonyl chloride 
• 685141-82-6 2(RS)-{2-[(3-methyl-1H-indene-2-carbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid ethyl ester 
• 1620107-42-7 N-((R)-1-(((S)-3-(4-methoxyphenyl)-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-3-phenylpropan-2-yl)amino)-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)-3-methyl-1H-indene-2-carboxamide 
• 1598433-50-1 C₂₅H₂₈N₂O₅ 
• 1620107-87-0 C₂₅H₂₈N₂O₅ 

Relevant academic research and scientific papers

AlBr3-mediated tandem cyclizationcarboxylation of allenylbenzenes with CO2 in the presence of pyridines

Indene-2-carboxylic acids are prepared from allenylbenzenes and CO2 by an AlBr3-mediated tandem reaction consisting of intramolecular FriedelCrafts alkylation of allenylbenzenes and subsequent carbonation of the resulting indenylaluminum species. The reaction requires 2,6- di-tert-butylpyridine or 2,6-diiodopyridine to neutralize an acidic by-product without deactivating the Lewis acid.

EtAlCl2/2,6-Disubstituted Pyridine-Mediated Carboxylation of Alkenes with Carbon Dioxide

α-Arylalkenes and trialkyl-substituted alkenes undergo carboxylation with CO2 in the presence of EtAlCl2 and 2,6-dibromopyridine to afford the corresponding α,β- and/or β,γ-unsaturated carboxylic acids. This reaction is suggested to proceed via the electrophilic substitution of EtAlCl2 with the aid of the base, followed by the carbonation of the resulting ate complex. This reaction can be applied to terminal dialkylalkenes by using a mixture of 2,6-di-tert-butylpyridine and 2,6-dibromopyridine.

Cyclization of arylacetoacetates to indene and dihydronaphthalene derivatives in strong acids. Evidence for involvement of further protonation of O,O-diprotonated β-ketoester, leading to enhancement of cyclization

The chemical features, such as substrate stability, product distribution, and substrate generality, and the reaction mechanism of Bronsted superacid-catalyzed cyclization reactions of aromatic ring-containing acetoacetates (β-ketoesters) were examined in detail. While two types of carbonyl cyclization are possible, i.e., keto cyclization and ester cyclization, the former was found to take place exclusively. The reaction constitutes an efficient method to synthesize indene and 3,4-dihydronapthalene derivatives. Acid-base titration monitored with 13C NMR spectroscopy showed that the acetoacetates are fully O1,O3-diprotonated at H 0) -11. While the five-membered ring cyclization of the arylacetoacetates proceeded slowly at H0) -11, a linear increase in the rate of the cyclization was found with increasing acidity in the high acidity region of H0) -11.8 to -13.3. Therefore, the O 1,O3-diprotonated acetoacetates exhibited some cyclizing reactivity, but they are not the reactive intermediates responsible for the acceleration of the cyclization in the high acidity region. The reactive cationic species might be formed by further protonation (or protosolvation) of the O1,O3-diprotonated acetoacetates; i.e., they may be tricationic species. Thermochemical data on the acid-catalyzed cyclization of the arylacetoacetates showed that the activation energy is decreased significantly as compared with that of the related acid-catalyzed cyclization reaction of a compound bearing a single functional group, such as a ketone. These findings indicate that intervention of the trication contributes to the activation of the cyclization of arylacetoacetates in strong acid, and the electron-withdrawing nature of the O-protonated ester functionality significantly increases the electrophilicity of the ketone moiety.

Studies on Indenoheterocycles: Part I - Synthesis of 9,9-Dimethyl-9H-indenopyridazin-1(2H)-ones

Starting from methyl 3-methyl-1H-indene-2-carboxylate (3) the bifunctional 3-formyl-1,1-dimethyl-1H-indene-2-carboxylate (6) has been obtained in high yield in two steps.The phenylhydrazones (8) of this compound undergo facile cyclisation to the title compounds, 2-substituted 9,9-dimethyl-9H-indenopyridazin-1(2H)-ones (9).However, the 2-unsubstituted indenopyridazinone (12) has been prepared employing two different routes starting from 6.