15791-03-4

Basic information

• Product Name: 3,3,6,6-Tetramethoxy-1,4-cyclohexadiene
• Synonyms: 3,3,6,6-TETRAMETHOXY-1,4-CYCLOHEXADIENE;1,4-BENZOQUINONE DIMETHYL DIACETAL;LABOTEST-BB LT00451944;1,4-Benzoquinone dimethyl diketal;p-Benzoquinone bis(dimethyl acetal)
• CAS NO: 15791-03-4
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.23
• Mol File: 15791-03-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 45-48 °C(lit.)
• Boiling Point: 60 °C/0.2 mmHg(lit.)
• Flash Point: 106 °C
• Appearance: /
• Density: 1.1508 (rough estimate)
• Vapor Pressure: 0.014mmHg at 25°C
• Refractive Index: 1.4580 (estimate)
• CAS DataBase Reference: 3,3,6,6-Tetramethoxy-1,4-cyclohexadiene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,6,6-Tetramethoxy-1,4-cyclohexadiene(15791-03-4)
• EPA Substance Registry System: 3,3,6,6-Tetramethoxy-1,4-cyclohexadiene(15791-03-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: 1759
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 15791-03-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 85, p. 2525, 1963 DOI: 10.1021/ja00899a044

InChI:InChI=1/C10H16O4/c1-11-9(12-2)5-7-10(13-3,14-4)8-6-9/h5-8H,1-4H3

Upstream product

• 67-56-1 methanol 
• 22774-66-9 N-propargyl-p-methoxyaniline 
• 1185-59-7 tetraethylammonium acetate 
• 150-78-7 1,4-dimethoxybezene 
• 2075-46-9 4-nitro-1H-pyrazole 
• 288-88-0 1,2,4-Triazole 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 953-12-8 1-(4-methoxyphenyl)-2-phenylhydrazine 
• 23990-91-2 2,4'-dimethoxy-4-methyldiphenyl ether 
• 124-41-4 sodium methylate 
• 1655-74-9 bis(4-methoxyphenyl) ether 
• 3402-85-5 1-methoxy-4-(p-tolyloxy)benzene 
• 1655-69-2 1-methoxy-4-phenoxy-benzene 
• 60316-51-0 2-bromo-1,1,4,4-tetramethoxycyclohexa-2,5-diene 

Downstream Products

• 72205-84-6 1,1,4,4-Tetraethoxy-1,4-dihydrobenzene 
• 110614-49-8 1,1,4,4-tetrakis(benzyloxy)-2,5-cyclohexadiene 
• 51506-44-6 1,4-Dimethoxy-2-[(2-methylpropyl)thio]benzol 
• 1129400-38-9 1,1,4-trimethoxy-4-(pyrazol-1-yl)cyclohexa-2,5-diene 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 516509-75-4 1,1,4-trimethoxy-4-(3-nitro-1,2,4-triazol-1-yl)cyclohexa-2,5-diene 
• 35357-33-6 1,4-benzoquinone bis(ethylene ketal) 
• 935-50-2 4,4-dimethoxycyclohexa-2,5-dienone 

Relevant articles and documents

Electrochemical N-arylation of azoles in MeOH using undivided electrolysis of their mixtures with 1,4-dimethoxyhenzene

The reactions of 1,4-dimethoxybenzene with azoles (pyrazole, triazole, and their derivatives, as well as tetrazole) were studied by undivided amperostatic electrolysis at Pt electrodes in MeOH. The process proceeds via the formation of a 1,1,4-trimethoxyarenonium cation as the key intermediate and affords 1,1,4,4-tetramethoxycyclohexa-2,5-diene, 1,1,4-trimethoxy-4-(azol-1-yl) cyclohexa-2,5-diene, and 1,4-dimethoxy-2-(azol-1-yl)benzene as the main products. Azole and solvent molecules compete as nucleophiles during electrolysis. A fine mechanism of the process was considered.

N-dimethoxyphenylation of highly basic pyrazoles during undivided electrolysis

The reactions of pyrazole, 3,5-dimethylpyrazole, and its 4-nitro derivatives with 1,4-dimethoxybenzene during undivided amperostatic electrolysis in MeCN (CH2Cl2) were studied. The basicity of the medium, which depends on the solvent

Development of a novel environmentally friendly electrolytic system by using recyclable solid-supported bases for in situ generation of a supporting electrolyte from methanol as a solvent: Application for Anodic methoxylation of organic compounds

We have successfully developed a novel environmentally friendly electrolytic system using recyclable solid-supported bases for in situ generation of a supporting electrolyte from methanol as a solvent. It was found that solid-supported bases are electrochemically inactive at an electrode surface. It was also found that solid-supported bases dissociate methanol into methoxide anions and protons. Therefore, in the presence of solid-supported bases, it was clarified that methanol serves as both a solvent and a supporting electrolyte generated in situ. Anodic methoxylation of various compounds with solid-supported bases was carried out to provide the corresponding methoxylated products in good to excellent yields with a few exceptions. The methoxylated products and the solid-supported bases were easily separated by only filtration, and the desired pure methoxylated products were readily isolated simply by concentration of the filtrates. The separated and recovered solid-supported bases were recyclable for several times.