286-75-9

Basic information

• Product Name: 5,10-dioxatricyclo[7.1.0.04,6]decane
• Synonyms: 5,10-dioxatricyclo[7.1.0.04,6]decane;DIEPOXYCYCLOOCTANE;1,5-Cyclooctadiene diepoxide
• CAS NO: 286-75-9
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.17968
• EINECS: 206-011-9
• Mol File: 286-75-9.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 313.9°Cat760mmHg
• Flash Point: 105°C
• Appearance: /
• Density: 1.153g/cm³
• CAS DataBase Reference: 5,10-dioxatricyclo[7.1.0.04,6]decane(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10-dioxatricyclo[7.1.0.04,6]decane(286-75-9)
• EPA Substance Registry System: 5,10-dioxatricyclo[7.1.0.04,6]decane(286-75-9)

Safety Data

• Hazardous Substances Data: 286-75-9(Hazardous Substances Data)

Usage

General Description

The chemical compound 5,10-dioxatricyclo[7.1.0.04,6]decane, also known as crown ether, is a cyclic polyether that contains three oxygen atoms in its ring structure. It is commonly used as a complexing agent for metal cations in various chemical and biological applications. Its unique structure allows it to selectively bind to specific metal ions, making it useful in applications such as ion selective electrodes, phase transfer catalysts, and as a host molecule in supramolecular chemistry. Additionally, crown ethers have been studied for their potential use in drug delivery systems and as components in materials science due to their ability to form stable complexes with various metal ions.

InChI:InChI=1/C8H12O2/c1-2-6-8(10-6)4-3-7-5(1)9-7/h5-8H,1-4H2

Upstream product

• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 73022-52-3 1,5-dimethyl-1,5-cyclooctadiene 
• 5259-72-3 cyclo-octa-1,5-diene 

Downstream Products

• 110-61-2 butanedinitrile 
• 1932267-11-2 9-(tert-butoxycarbonyl)-9-azabicyclo[3.3.1]nona-2,6-diene 

Relevant articles and documents

Iron-Catalyzed Epoxidation of Linear α-Olefins with Hydrogen Peroxide

The combination of Fe(OTf)2 with N-methyl bis(picolylamine) (Me-bpa) L7 enables epoxidation of linear olefins including terminal, internal, and cyclic ones, using hydrogen peroxide as terminal oxidant under mild conditions. In the presence of picolinic acid as additive improved yields of epoxides up to 75 % have been achieved.

Efficient and region-selective conversion of octanes to epoxides under ambient conditions: Performance of tri-copper catalyst, [Cu3I(L)]+1 (L=7-N-Etppz)

In this paper, is described the conversion of the octane group of hydrocarbons into industrially important epoxides using tri-copper catalyst, [Cu3I(L)]+1 (L=7-N-Etppz). The role of hydrogen peroxide as a sacrificial oxygen donor during catalytic conversion to epoxides has been investigated. The performance of the catalyst has been evaluated in terms of turnover numbers (TON) and turnover frequencies (TOF) reported in this article.

Electronic Structure and Multicatalytic Features of Redox-Active Bis(arylimino)acenaphthene (BIAN)-Derived Ruthenium Complexes

The article examines the newly designed and structurally characterized redox-active BIAN-derived [Ru(trpy)(R-BIAN)Cl]ClO4 ([1a]ClO4-[1c]ClO4), [Ru(trpy)(R-BIAN)(H2O)](ClO4)2 ([3a](ClO4)2-[3c](ClO4)2), and BIAO-derived [Ru(trpy)(BIAO)Cl]ClO4 ([2a]ClO4) (trpy = 2,2′:6′,2′′-terpyridine, R-BIAN = bis(arylimino)acenaphthene (R = H (1a+, 3a2+), 4-OMe (1b+, 3b2+), 4-NO2 (1c+, 3c2+), BIAO = [N-(phenyl)imino]acenapthenone). The experimental (X-ray, 1H NMR, spectroelectrochemistry, EPR) and DFT/TD-DFT calculations of 1an-1cn or 2an collectively establish {RuII-BIAN0} or {RuII-BIAO0} configuration in the native state, metal-based oxidation to {RuIII-BIAN0} or {RuIII-BIAO0}, and successive electron uptake processes by the α-diimine fragment, followed by trpy and naphthalene π-system of BIAN or BIAO, respectively. The impact of the electron-withdrawing NO2 function in the BIAN moiety in 1c+ has been reflected in the five nearby reduction steps within the accessible potential limit of -2 V versus SCE, leading to a fully reduced BIAN4- state in [1c]4-. The aqua derivatives ({RuII-OH2}, 3a2+-3c2+) undergo simultaneous 2e-/2H+ transfer to the corresponding {RuIV-O} state and the catalytic current associated with the RuIV/RuV response probably implies its involvement in the electrocatalytic water oxidation. The aqua derivatives (3a2+-3c2+) are efficient and selective precatalysts in transforming a wide variety of alkenes to corresponding epoxides in the presence of PhI(OAc)2 as an oxidant in CH2Cl2 at 298 K as well as oxidation of primary, secondary, and heterocyclic alcohols with a large substrate scope with H2O2 as the stoichiometric oxidant in CH3CN at 343 K. The involvement of the {RuIV-O} intermediate as the active catalyst in both the oxidation processes has been ascertained via a sequence of experimental evidence.