122-95-2

Usage

Uses

1. Used in Organic Synthesis:
1,4-Diethoxybenzene is used as an intermediate in the field of organic synthesis for the production of various chemicals and compounds. Its versatile structure allows it to be a valuable building block in the synthesis of a wide range of organic molecules.
2. Used in the Synthesis of Pillar[6]arene:
1,4-Diethoxybenzene is used as a key component in the synthesis of pillar[6]arene, a type of macrocyclic molecule with potential applications in supramolecular chemistry and materials science. The synthesis of pillar[6]arene typically involves the use of boron trifluoride etherate (BF3.OEt2) as a catalyst, which facilitates the formation of the macrocyclic structure.

InChI:InChI=1/C10H14O2/c1-3-11-9-5-7-10(8-6-9)12-4-2/h5-8H,3-4H2,1-2H3

Upstream product

• 57246-14-7 Tetraethyl 1,4-phenylene bis(phosphate) 
• 75-03-6 ethyl iodide 
• 123-31-9 hydroquinone 
• 74-96-4 ethyl bromide 
• 64-67-5 diethyl sulfate 
• 78-40-0 triethyl phosphate 
• 546-74-7 sodium ethyl sulfate 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 30008-10-7 sodium 4-hydroxybenzen-1-olate 
• 106-37-6 1.4-dibromobenzene 
• 141-52-6 sodium ethanolate 
• 1569262-64-1 ethyl N-tert-butyl-4-nitrobenzenesulfonimidate 
• 622-62-8 4-Ethoxyphenol 
• 106-41-2 4-bromo-phenol 

Downstream Products

• 63213-46-7 3-(2,5-diethoxybenzoyl)propanoic acid 
• 56150-29-9 1,4-diethoxy-2,5-bis(chloromethyl)benzene 
• 103861-41-2 1,4-diethoxy-2-chloromethyl-benzene 
• 4686-98-0 2,5-diethoxybenzaldehyde 
• 102942-88-1 1,4-diethoxy-2,5-dinitro-benzene 
• 90870-51-2 2,3-Dinitrohydroquinone diethyl ether 
• 119-23-3 2,5-diethoxy-1-nitrobenzene 
• 37158-04-6 2,5-diethoxy-benzenesulfonic acid amide 
• 312325-40-9 1,4-diethoxy-2,3,5-trinitro-benzene 
• 1937-92-4 1-(2,5-diethoxy-phenyl)-propan-1-one 
• 112434-80-7 1-(2,5-diethoxy-phenyl)-ethanone 
• 75631-63-9 trichloro-acetic acid-(4-ethoxy-phenyl ester) 
• 857564-04-6 2,5-diethoxy-deoxybenzoin 
• 73010-48-7 3,6-diethoxy-3,6-dimethoxycyclohexa-1,4-diene 

Relevant academic research and scientific papers

Tuning the moisture and thermal stability of metal-organic frameworks through incorporation of pendant hydrophobic groups

An isostructural series of NbO-type porous metal-organic frameworks (MOFs) with different dialkoxy-substituents of formula Cu2(TPTC-OR) (TPTC-OR = 2′,5′-di{alkyl}oxy-[1,1′:4′,1″-terphenyl]-3, 3″,5,5″-tetracarboxylate, R = Me, Et, nPr, nHex) has been synthesized and characterized. The moisture stability of the materials has been evaluated, and a new superhydrophobic porous MOF has been identified. The relationship between pendant side chain length and thermal stability has been analyzed by in situ synchrotron powder X-ray diffraction, showing decreased thermal stability as the side chain length is increased, contradictory to thermogravimetric decomposition studies. Additionally, the four materials exhibit moderate Brunauer-Emmett-Teller (BET) and Langmuir surface areas (1127-1396 m2 g-1 and 1414-1658 m2 g -1) and H2 capacity up to 1.9 wt % at 77 K and 1 bar.

Substituted poly(p-phenylene) thin films via Surface-Initiated Kumada-Type catalyst transfer polycondensation

Conjugated polymer films of unsubstituted and alkoxy-substituted poly(p-phenylene) have been prepared via a Kumada-type catalyst-transfer polycondensation in a grafting-from configuration. A surface-bound external initiator was formed by reacting a Ni(O) complex with a thienyl bromide monolayer, and this surface-bound initiator was used to polymerize several Grignard monomers prepared from the corresponding 1,4-dihalobenzenes resulting in surface-bound, conjugated polymer chains with thickness up to 30 nm. A series of 1,4-diodo monomers with alkoxy side chains ranging from unsubstituted 1,4-diiodobenzene to 1,4-diiodo-2,5-dihexyloxybenzene were polymerized in order to explore the influence of steric bulk on the surface-initiated polymerization process. Within the series of molecules, it was observed that monomers with smaller, less bulky side chains were more easily polymerized from the surface, resulting in smooth, regular films for unsubstituted and methoxy-substituted polyphenylene. Islands of polymer growth were observed with the ethoxy-substituted material and only sparse, irregular growth for the hexyloxysubstituted polymer. The resulting films were characterized by AFM., infrared spectroscopy, ellipsometry, and UV-vis spectroscopy.

Synthesis of p-Di[1-13C]ethoxybenzene from [1-13C]iodoethane with high labeling efficiency

p-Di[1-13C]ethoxybenzene was synthesized in high yield and with high labeling efficiency from hydroquinone and [1-13C]iodoethane in the presence of a base in dry acetone. Some p-[1-13C]ethoxyphenol was also formed, from which further p-di[1-13C]ethoxybenzene could be synthesized.

Light assisted O-alkylation of phenols to ethers using layered double oxides catalyst under green and mild conditions

O-alkylation of phenols with dialkyl carbonates to ethers over layered double oxides (LDOs) catalyst under light irradiation is described. A base additive is not required when using the longer-chain diethyl carbonate as an alkylating agent owing to the sufficient basicity provided by LDOs. The synergism of substrate phenols molecules absorbing light to reach the first excited states with acid–base pairs of catalyst enhanced the interaction of reactant molecules with the surface of LDOs, simultaneously accelerating the cleavage of phenolic hydroxyl groups. A variety of phenols are tolerated in this system. This work reports a simple and environmentally benign catalytic process for the dehydrogenation of phenolic hydroxyl groups.

Double-triazole substituted ethoxy compound and its preparation method and application

The invention discloses a double-triazole substituted ethoxy benzene compound and a preparation method and application thereof. The organic compound is prepared by conducting reflux reaction on 1,4-bis (bromomethyl)-2,5-diethoxy benzene with 3-(1H-1,2,4-triazole-1-yl) propionitrile in acetonitrile, and then conducting basic hydrolysis. The preparation method of the present invention has the characteristics of simple operation, low production cost and little environmental pollution, and is applicable to large scale industrialization production. The compound prepared by the invention can be applied to the research on bactericide. The experimental results confirm that the double-triazole substituted ethoxy benzene compound has certain sterilization activity on Escherichia coli and Staphylococcus aureus, especially significant bactericidal activity against Staphylococcus aureus.

Solvent-free synthesis of pillar[6]arenes

An efficient solvent-free procedure for the synthesis of pillar[6]arenes has been developed. The procedure involves the solid-state condensation of finely milled 1,4-dialkoxybenzene and paraformaldehyde by grinding in the presence of a catalytic amount of H2SO4. The use of organic solvents for the extraction of products has also been avoided. Operational simplicity, compatibility with various 1,4-dialkoxybenzenes, non-chromatographic purification technique, high yields and mild reaction conditions are the notable advantages of this procedure. A large scale reaction demonstrated the practical applicability of this methodology.

Practical Ligand-Free Copper-Catalysed Short-Chain Alkoxylation of Unactivated Aryl Bromides

An efficient and practical short-chain alkoxylation of unactivated aryl bromides has been developed with special attention focussed on the applicability of the reaction. Sodium alkoxide is used as the nucleophile, and the corresponding alcohol as the solvent. The reaction requires neither precious metals nor organic ligands. It uses a catalytic system consisting of copper(I) bromide as a catalyst, the corresponding alkyl formate as a noncontaminating cocatalyst, and lithium chloride as an additive. A wide range of substrates and test cases highlight the synthetic utility of the approach. Considering the commercial accessibility and affordability of the feedstocks, this protocol shows promise as a new alternative for the sustainable preparation of aryl alkyl ethers.

Synthesis and surfactochromicity of 1,4-diketopyrrolo[3,4-c]pyrrole(DPP)- based anionic conjugated polyelectrolytes

Two novel anionic conjugated copolyelectrolytes PSDPPPV and PSDPPPE were synthesized via Heck/Sonogashira coupling reactions and characterized by FT-IR, 1H NMR, UV-vis, and PL spectroscopy. The two polymers are respectively constituted of 2,5-diethoxy-1,4-phenyleneethynylene (DPV) and 2,5-diethoxy-1,4-phenyleneethynylene (DPE) with 1,4-diketo-2,5-bis(4- sulfonylbutyl)-3,6-diphenylpyrrolo[3,4-c]pyrrole (SDPP) which is a novel water soluble diketopyrrolopyrrole derivative. PSDPPPV and PSDPPPE show broad absorption band in visible region and they exhibit strong fluorescence quenching in aqueous solution. The fluorescence of their aqueous solutions can be enhanced in the presence of cationic surfactant or polymer nonionic surfactant. Fluorescence enhancement by introduction of polyvinylpyrrolidone (PVP) shows linear response. This result provides a controllable method to increase fluorescence intensity of dipyrrolopyrrole-based conjugate polyelectrolytes in aqueous phase. The optical properties suggested that PSDPPPV and PSDPPPE which are negatively charged conjugated polymers can assemble with positively charged photovoltaic materials to form ionic photoactive layer.

SNAAP sulfonimidate alkylating agent for acids, alcohols, and phenols 1

Stable, crystalline ethyl N-tert-butyl-4-nitrobenzenesulfonimidate has been prepared in high yield by direct O-ethylation of N-tert-butyl-4- nitrobenzenesulfonamide with iodoethane and silver(I) oxide in dichloromethane. This sulfonimidate directly ethylates various acids to esters; the stronger the acid, the faster it alkylates and in higher yield. It readily ethylates alcohols and phenols to ethers at room temperature in the presence of tetrafluoroboric acid catalyst without molecular rearrangements or racemization. We have defined these reactions as SNAAP alkylations: [substitution, nucleophilic of acids, alcohols and phenols]. The hard sulfonimidate alkylating agent is chemoselective, preferring oxygen > nitrogen > sulfur. The sulfonamide byproduct of alkylation is readily recycled to the sulfonimidate. Georg Thieme Verlag Stuttgart . New York.

Copper(II) ion-sensing mechanism of oligo-phenylene vinylene derivatives: Syntheses and theoretical calculations

Oligo-phenylene vinylene (oligo-PV) with two picolinamide side-groups and six methoxy end-groups was synthesized in order to be a fluorescent sensing molecule. Various metal ion solutions (1.5×10-4 M) were added to the 1.5×10-6 M acetonitrile solution of the fluorescent molecule. The fluorescent emission spectra showed that, at about the same concentration (1.5×10-4 M), only Cu(II) ion can quench the fluorescent emission of the picolinamide-PV solution. Possible metal ion-sensing mechanisms could be either the binding at picolinamide side-groups or methoxy end-groups, or interchain-stacking driven by the metal ions. Hence, oligo-PVs with six methoxy end-groups but without substituted side-groups, and another oligo-PV with six methoxy end-groups and two ethoxy side-groups were synthesized for comparison. These molecules turned out to be inactive to any metal ion solutions. Moreover, quantum calculation was used to confirm the result. Binding energy and conformation were calculated and simulated. It could be concluded that nitrogen and oxygen atoms of the picolinamide group and one oxygen atom from the methoxy group are involved in the metal ion-binding process.