64179-67-5

Basic information

• Product Name: 2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBALDEHYDE
• Synonyms: 2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBALDEHYDE;1,4-BENZODIOXAN-2-CARBOXALDEHYDE;1,4-Benzodioxin-2-carboxaldehyde, 2,3-dihydro-;2,3-dihydro-1,4-benzodioxine-2-carbaldehyde;2,3-Dihydrobenzo[b][1,4]dioxine-2-carbaldehyde
• CAS NO: 64179-67-5
• Molecular Formula: C9H8O3
• Molecular Weight: 164.16
• Mol File: 64179-67-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 265.892 °C at 760 mmHg
• Flash Point: 105.236 °C
• Appearance: /
• Density: 1.314 g/cm³
• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: 2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBALDEHYDE(64179-67-5)
• EPA Substance Registry System: 2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBALDEHYDE(64179-67-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 64179-67-5(Hazardous Substances Data)

Usage

General Description

2,3-Dihydro-benzo[1,4]dioxine-2-carbaldehyde is a chemical compound with the molecular formula C9H8O2. It is an aldehyde derivative of benzo[1,4]dioxine, with a benzene ring fused to a 1,4-dioxine ring. 2,3-DIHYDRO-BENZO[1,4]DIOXINE-2-CARBALDEHYDE is used in the synthesis of pharmaceuticals and agrochemicals. It has also been studied for its potential antibacterial and antifungal properties. Additionally, 2,3-dihydro-benzo[1,4]dioxine-2-carbaldehyde has been investigated for its potential use in the development of new materials and as a building block for the synthesis of other compounds.

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 articles and documents

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.).