64179-67-5

Usage

Uses

Used in Pharmaceutical Synthesis:
2,3-Dihydro-benzo[1,4]dioxine-2-carbaldehyde is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Synthesis:
2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBALDEHYDE is also utilized in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products to improve crop protection and yield.
Used in Antibacterial Applications:
2,3-Dihydro-benzo[1,4]dioxine-2-carbaldehyde has been studied for its potential antibacterial properties. It can be used as an active ingredient in the development of new antimicrobial agents to combat bacterial infections.
Used in Antifungal Applications:
2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBALDEHYDE has also been investigated for its antifungal properties, making it a potential candidate for the development of new antifungal agents to treat fungal infections.
Used in Material Science:
2,3-Dihydro-benzo[1,4]dioxine-2-carbaldehyde has been explored for its potential use in the development of new materials. Its unique structure and properties can contribute to the creation of innovative materials with specific characteristics for various applications.
Used as a Building Block in Organic Synthesis:
2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBALDEHYDE serves as a valuable building block for the synthesis of other organic compounds. Its versatile structure allows for further chemical modifications and the development of new molecules with diverse applications across different industries.

InChI:InChI=1/C9H8O3/c10-5-7-6-11-8-3-1-2-4-9(8)12-7/h1-5,7H,6H2

Upstream product

• 3663-79-4 methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate 
• 1008-92-0 2-cyano-1,4-benzodioxane 
• 1616377-88-8 rac-2-N,N-dichloroaminomethyl-1,4-benzodioxane 
• 4442-59-5 (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine 

Downstream Products

• 1384516-18-0 C₂₁H₁₉ClN₂O₄S 

Relevant academic research and scientific papers

Catalyst-Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor-Acceptor Complex Photoactivation

A catalyst- and additive-free decarbonylative trifluoromethylthiolation of aldehyde feedstocks has been developed. This operationally simple, scalable, and open-to-air transformation is driven by the selective photoexcitation of electron donor-acceptor (EDA) complexes, stemming from the association of 1,4-dihydropyridines (donor) with N-(trifluoromethylthio)phthalimide (acceptor), to trigger intermolecular single-electron transfer events under ambient- and visible light-promoted conditions. Extension to other electron acceptors enables the synthesis of thiocyanates and thioesters, as well as the difunctionalization of [1.1.1]propellane. The mechanistic intricacies of this photochemical paradigm are elucidated through a combination of experimental efforts and high-level quantum mechanical calculations [dispersion-corrected (U)DFT, DLPNO-CCSD(T), and TD-DFT]. This comprehensive study highlights the necessity for EDA complexation for efficient alkyl radical generation. Computation of subsequent ground state pathways reveals that SH2 addition of the alkyl radical to the intermediate radical EDA complex is extremely exergonic and results in a charge transfer event from the dihydropyridine donor to the N-(trifluoromethylthio)phthalimide acceptor of the EDA complex. Experimental and computational results further suggest that product formation also occurs via SH2 reaction of alkyl radicals with 1,2-bis(trifluoromethyl)disulfane, generated in-situ through combination of thiyl radicals. (Figure presented.).

From 2-aminomethyl-1,4-benzodioxane enantiomers to unichiral 2-cyano- and 2-carbonyl-substituted benzodioxanes via dichloroamine

2-Substituted 1,4-benzodioxanes, such as 2-cyano-, 2-methoxycarbonyl-, 2-aminocarbonyl-, and 2-formyl-1,4-benzodioxane, are key synthons that for the most part are never described as enantiomers or are inadequately characterized for enantiomeric purity. They were prepared by quantitative N,N-dichlorination of (R)- and (S)-2-aminomethyl-1,4-benzodioxane and successive functional group conversions in high yields without any racemization of the stereogenic benzodioxane C(2).