61364-25-8

Usage

Uses

Used in Chemical Synthesis:
2,5-DIMETHYL-1H-INDOLE-3-CARBALDEHYDE is used as a building block for the synthesis of various chemical compounds. Its unique molecular structure allows it to be a versatile component in the creation of a wide array of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals. 2,5-DIMETHYL-1H-INDOLE-3-CARBALDEHYDE's reactivity and functional groups make it a valuable asset in the development of new and innovative products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,5-DIMETHYL-1H-INDOLE-3-CARBALDEHYDE is used as a key intermediate in the synthesis of various drugs and drug candidates. Its unique structure and reactivity enable the development of novel therapeutic agents with potential applications in treating a range of diseases and medical conditions.
Used in Agrochemical Industry:
2,5-DIMETHYL-1H-INDOLE-3-CARBALDEHYDE also finds application in the agrochemical industry, where it is used as a building block for the synthesis of various agrochemical products, such as pesticides and herbicides. Its unique properties allow for the development of new and effective compounds that can help address challenges in agriculture, such as pest control and crop protection.
Used in Flavor and Fragrance Industry:
In the flavor and fragrance industry, 2,5-DIMETHYL-1H-INDOLE-3-CARBALDEHYDE is used as a starting material for the creation of various aroma compounds. Its unique molecular structure contributes to the development of new and distinct scents, which can be used in a wide range of products, from perfumes and colognes to household and personal care items.
Used in Dye and Pigment Industry:
2,5-DIMETHYL-1H-INDOLE-3-CARBALDEHYDE is also utilized in the dye and pigment industry, where it serves as a building block for the synthesis of various colorants. Its unique chemical properties enable the development of new and vibrant dyes and pigments, which can be used in a variety of applications, including textiles, plastics, and coatings.

InChI:InChI=1/C11H11NO/c1-7-3-4-11-9(5-7)10(6-13)8(2)12-11/h3-6,12H,1-2H3

Upstream product

• 1196-79-8 2,5-Dimethyl-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 

Relevant academic research and scientific papers

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.

Synthesis of Chiral Polycyclic Tetrahydrocarbazoles by Enantioselective Aminocatalytic Double Activation of 2-Hydroxycinnamaldehydes with Dienals

An efficient aminocatalytic enantioselective double-activation strategy has been developed that combines several different aminocatalytic modes in a cascade process, such as iminium ion, vinylogous iminium ion, trienamine, and dienamine activations. By using this strategy, 2-hydroxycinnamaldehydes worked well with various dienals via [4 + 2] cycloaddition and the oxa-Michael reaction-initiated cascade, respectively, leading to chiral polycyclic tetrahydrocarbazole and chromane derivatives with excellent diastereo- and enantioselectivities.

Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives

A simple and effective one-pot synthesis of substituted indolo[1,2-a]quinolines has been developed. The desired products were obtained in up to 98% yield when substituted 2-methyindoles were treated with 2-iodobenzaldehyde in the presence of Cs2CO3, CuI and L-proline. Our mechanistic study confirmed that the reaction sequence involved an intermolecular Knoevenagel reaction followed by an intramolecular Ullmann-type coupling reaction. Moreover, some of the synthesized compounds were found to be active against human breast (MCF-7) and colorectal (HCT-116) cancer cells with IC50 values of 27.96 μM and in the range of 6.21–46.91 μM, respectively.

Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals

The direct and rapid construction of carbazoles was achieved via the reaction of 2-methyl-indole-3-carbaldehydes with enals promoted by LiCl/DBU in a single operation. This mild and green reaction proceeds through a [4 + 2] cycloaddition/dehydration/oxidative aromatization cascade to generate carbazoles in good to excellent yields. The reaction features mild reaction conditions, a broad substrate scope, and excellent functional group tolerance, using O2 (1 atm) as the sole oxidant and affording H2O as the only by-product. More importantly, 4-fluoroquinocarbazole, a significant bioactive compound, was generated in 80% yield in only one step from the obtained carbazole.

One-pot synthesis of substituted indolo[1,2-a]quinolines under transition-metal-free conditions

A simple and efficient one-pot synthesis of substituted indolo[1,2-a]quinolines under transition-metal-free conditions has been developed. When 2-fluorobenzaldehyde was treated with substituted 2-methylindoles in the presence of Cs2CO3, the desired products were typically obtained in good to excellent yields. This reaction sequence involves a nucleophilic aromatic substitution and a Knoevenagel condensation reaction. Our mechanistic investigation revealed that both reactions could proceed as an intermolecular reaction in the first step.