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Usage

Uses

Used in Pharmaceutical and Agricultural Chemical Industries:
1,5-DIMETHYL-1H-INDOLE-2-CARBALDEHYDE is used as a building block in the synthesis of various pharmaceuticals and agricultural chemicals. Its unique chemical structure allows for the creation of a wide range of compounds with different therapeutic and pesticidal properties.
Used in Fragrance Industry:
1,5-DIMETHYL-1H-INDOLE-2-CARBALDEHYDE is used as a fragrance ingredient to produce scents with a floral, woody, or fruity aroma. Its ability to impart pleasant and complex scents makes it a valuable component in the formulation of perfumes, colognes, and other fragrance products.
Used in Biomedical Research:
1,5-DIMETHYL-1H-INDOLE-2-CARBALDEHYDE has shown potential as a fluorescent probe in biomedical research. It can be used for detecting and imaging specific proteins and cellular structures, aiding in the study of various biological processes and diseases.
It is important to handle and store 1,5-DIMETHYL-1H-INDOLE-2-CARBALDEHYDE with caution, as it may pose health risks if not properly managed.

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

Upstream product

• 16382-15-3 5-methyl-1H-indole-2-carboxylic acid ethyl ester 
• 27816-53-1 1,5-dimethyl-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 614-96-0 5-methyl-1H-indole 
• 102870-03-1 5-methylindole-2-carboxylic acid methyl ester 
• 10241-97-1 5-methylindole-2-carboxylic acid 
• 167478-82-2 methyl-1,5-dimethyl-1H-indole-2-carboxylate 
• 943117-52-0 C₁₁H₁₃NO 
• 67929-99-1 ethyl 1,5-dimethyl-indole-2-carboxylate 

Downstream Products

• 1305306-37-9 C₂₁H₁₉N 
• 1627687-20-0 C₂₆H₃₅NO₃ 
• 1627687-21-1 1-(1,5-dimethyl-1H-indol-2-yl)-4-cyclohexylpenta-2,3-dien-1-ol 
• 1627687-45-9 3-cyclohexyl-4,6,9-trimethyl-9H-carbazole 

Relevant academic research and scientific papers

Synthesis of Carbazoles and Dihydrocarbazoles by a Divergent Cascade Reaction of Donor-Acceptor Cyclopropanes

An alkylation/olefination cascade of indolecarboxaldehydes and phosphonate-functionalized donor-acceptor cyclopropanes affords functionalized dihydrocarbazoles and cyclohepta[cd]indoles in formal (3 + 3) and (4 + 3) cycloadditions. A minor modification to the reaction conditions also allows access to the fully aromatic heterocyclic scaffolds by thermal loss of an electron-rich aryl moiety.

Cycloaddition of in Situ Formed Azaoxyallyl Cations with 2-Alkenylindoles: An Approach to Tetrahydro-β-carbolinones

A novel [3 + 3] cycloaddition between in situ formed azaoxyallyl cations and 2-alkenylindoles has been developed. This concise method allows the efficient construction of a series of tetrahydro-β-carbolinones in good yields under mild conditions. Gram-sca

Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines

An efficient zinc(II)-catalyzed alkyne oxidation/C￡H functionalization sequence was developed, thus leading to highly site-selective synthesis of a variety of isoquinolones and β-carbolines. Importantly, in contrast to the well-established gold-catalyzed intermolecular alkyne oxidation, over-oxidation can be completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theoretical calculations are described.

Construction of Benzo[c]carbazoles and Their Antitumor Derivatives through the Diels-Alder Reaction of 2-Alkenylindoles and Arynes

The direct assembly of benzo[c]carbazole derivatives via the Diels-Alder reaction of arynes and easily accessible 2-alkenylidoles was reported. By employing different aryne precursor loads, 6,7-dihydrobenzo[c]carbazoles or aryl-substituted 7,11b-dihydrobenzo[c]carbazoles could be controllably generated in good to excellent yields under a nitrogen atmosphere. On the other hand, when the reaction was conducted under oxygen, oxidated/aromatized product benzo[c]carbazoles could be generated directly with high selectivity and efficiency in a one-step manner. Interestingly, the benzo[c]carbazole-5-carboxamide amidation derivatives of the above products showed good antitumor activities. The inhibitory effect of these molecules against cancer cells was also described.

Synthesis of carbazoles by gold(I)-catalyzed carbocyclization of 2-(enynyl)indoles

A new synthetic protocol for carbazoles through gold(I)-catalyzed intramolecular hydroarylation of (Z)-2-(enynyl)indoles was achieved in good yields. The requisite (Z)-2-(enynyl)indoles were synthesized stereoselectively by trimethylgallium-promoted, Z-selective Wittig olefination of N-alkylindole-2-carboxaldehydes with propargyl ylides. Substrates possessing both alkyl as well as aromatic groups are well tolerated under these reaction conditions. Georg Thieme Verlag Stuttgart.