3450-15-5

Usage

Appearance

Yellow crystalline substance

Common uses

Reagent in organic synthesis, building block for various chemical reactions, production of pharmaceuticals and agrochemicals

Known for

High stability and selective reactivity

Handling and storage

Must be handled and stored with care due to potential hazards if not properly managed.

Upstream product

• 928-49-4 hex-3-yne 
• 137039-62-4 1,4-dihydroxy-2,3,5,6-tetraethylbenzene 
• 77922-77-1 1,2,4,5-tetraethyl-3,6-dinitro-benzene 
• 2715-54-0 1-(2,4,5-triethylphenyl)ethanone 
• 635-81-4 1,2,4,5-tetraethylbenzene 
• 877-44-1 1,2,4-triethylbenzene 
• 201230-82-2 carbon monoxide 
• 137039-59-9 1,4-dimethoxy-2,3,5,6-tetraethylbenzene 
• 604-88-6 hexaethylbenzene 
• 58244-25-0 2,3,5,6-tetraethyl-p-phenylenediamine 

Downstream Products

• 137039-62-4 1,4-dihydroxy-2,3,5,6-tetraethylbenzene 
• 137039-59-9 1,4-dimethoxy-2,3,5,6-tetraethylbenzene 

Relevant academic research and scientific papers

Rhodium-catalyzed [2+2+1+1] cyclocarbonylative coupling of alkynes with carbon monoxide affording tetrasubstituted p-benzoquinones

In this strategy, the tetrasubstituted benzoquinones have been prepared directly by a [2+2+1+1] cyclocarbonylative coupling reaction of internal alkynes with CO in the presence of [RhCl(CO)2]2. The low concentration of CO in the reaction is the crucial point for the chemoselective formation of tetrasubstituted benzoquinones in good to high yields. Functional groups such as chloro, methoxy, cyano, vinyl, fluoro, and carboxylate are tolerated under the reaction conditions.

Control of functional group proximity and direction by conformational networks: Synthesis and stereodynamics of persubstituted arenes

The cooperative nonbonded interactions present in hexaethylbenzene result in an arrangement of alkyl groups such that the 1,3,5 and 2,4,6 substituents point to opposite faces of the benzene ring. Correspondingly, derivatives of hexaethylbenzene have their functional groups convergent (meta as in 1,3,5-trisubstituted-2,4,6-triethylbenzene) or divergent (ortho, para as in 1,2-disubstituted-3,4,5,6-tetraethylbenzenes or 1,4-disubstituted-2,3,5,6-tetraethylbenzenes) due to this cooperative conformational network. To illustrate this structural feature and probe its dynamics, 1,4-di-X-2,3,5,6-tetraethylbenzenes have been synthesized. The dynamic stereochemistry of the disubstituted compounds has been studied by variable temperature 1H NMR spectroscopy. Using the same strategy, the 1,3,5-tris(CH2Y)-2,4,6-triethylbenzenes have also been prepared. The steric bulk of the substituent in the disubstituted compounds has been found to influence the barrier height. The trends found are applicable for the use of these compounds as angular building blocks for the design of ligands, polymers, and supramolecular architectures.

Oxidative Dealkylation of Hydroquinone Ethers with Nitrogen Dioxide in the Convenient Preparation of Quinones

Various Hydroquinone dialkyl ethers (R2Q) are effectively converted by nitrogen dioxide into the corresponding quinone (Q) and alkyl nitrite (RONO) in dichloromethane at room temperature or below.The preparative procedure for the isolation of crystalline quinones in quantitative yield merely involves the convenient removal of the low boiling solvent in vacuo.Isotopic labelling studies demonstrate that the oxidative dealkylation proceeds via alkoxy scission of the labile cation radical (R2Q-cation radical) formed via the oxidation of the hydroquinone ether by nitrogen dioxide ( as the disproportionated ion pair NO+NO3-).The electron-transfer mechanism is confirmed by the spectral observation of R2Q-cation radical (identified by the isolation of the crystalline salt R2Q-cation radical-SbCl6-) and its rapid conversion into quinone and alkyl nitrite by combination with nitrate (NO3-) and nitric oxide (NO).

Convenient Preparation of Quinones via the catalytic Autoxidation of Hydroquinones with Nitrogen Oxides

An efficient, inexpensive, catalytic method for the autoxidation of hydroquinones utilizes the gaseous (NOx) catalyst which allows a simple workup procedure for quinone isolation merely by solvent removal.

Novel Catalysis of Hydroquinone Autoxidation with Nitrogen Oxides

An efficient catalytic method is described for the preparative conversion of hydroquinones to quinones with dioxygen under mild conditions.The use of the gaseous nitrogen oxide (NOx) catalyst allows a simple workup procedure for the isolation of quinones in essentially quantitative yields by merely removing the low-boiling solvent dichloromethane in vacuo.The mechanism of the catalytic autoxidation of hydroquinones is ascribed to the critical role of nitrosonium (NO(+)) in the one-electron oxidation of hydroquinone, followed by the reoxidation of the reduced nitric oxide (NO) with dioxygen.An extensive series of complex interchanges among various NOx species in nitrogen-(V), -(IV), -(III), and -(II) oxidation states, coupled with stepwise oxidation of hydroquinone via a successive series of one-electron/proton transfer, from the critical components of the catalytic cycle.

Effect of transition-metal complexation on the stereodynamics of persubstituted arenes. Evidence for steric complementarity between arene and metal tripod

The stereodynamics in l,4-dimethoxy-2,3,5,6-tetraethylbenzene (5), 1,4-bis(metboxymethyl)-2,3,5,6-tetracthylbenzene (6), and l,4-dineohexyl-2,3,5,6-tetraethylbenzene (7) and their respective tricarbonylchromium complexes, 5(Cr), 6(Cr), and 7(Cr), have bee