1,3-Cyclohexadiene

Base Information

• Chemical Name: 1,3-Cyclohexadiene
• CAS No.: 592-57-4
• Deprecated CAS: 33004-09-0
• Molecular Formula: C6H8
• Molecular Weight: 80.1295
• Hs Code.: 29021990
• European Community (EC) Number: 249-853-2,209-764-1
• ICSC Number: 0762
• UN Number: 1993
• UNII: JV5W0EG5BP
• DSSTox Substance ID: DTXSID30862259
• Nikkaji Number: J1.855.158F,J1.855.159D,J94.915I
• Wikipedia: Cyclohexa-1,3-diene
• Wikidata: Q387320
• Metabolomics Workbench ID: 55637
• Mol file: 592-57-4.mol

Synonyms:1,3-cyclohexadiene

Chemical Property of 1,3-Cyclohexadiene

Chemical Property:

• Appearance/Colour: clear colorless to light yellow liquid
• Vapor Pressure: 55.7mmHg at 25°C
• Melting Point: -98 °C
• Refractive Index: n20/D 1.474(lit.)
• Boiling Point: 80 °C(lit.)
• Flash Point: °C
• PSA: 0.00000
• Density: 0.861g/cm³
• LogP: 1.89260
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly miscible with methanol. Immiscible with water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 80.062600255
• Heavy Atom Count: 6
• Complexity: 66

Purity/Quality:

99.3% ^*data from raw suppliers

1,3-Cyclohexadiene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): FXi
• Hazard Codes: F
• Statements: 11-10-37
• Safety Statements: 9-16-29-33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: C1CC=CC=C1
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract.
• Uses: 1,3-Cyclohexadiene can undergo: C-C coupling with aromatic alcohols via iridium-catalyzed hydrogen auto-transfer and with aldehydes via transfer hydrogenation mediated by isopropanol to form carbonyl addition products. Living anionic polymerization with n-BuLi/TMEDA system to form polycyclohexadiene. Platinum-catalyzed silaboration to form (1R,4S)-1-(dimethylphenylsilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclohexene. Aerobic palladium-catalyzed 1,4-diacetoxylation in the presence of cobalt tetra(hydroquinone)porphyrin as an electron transfer reagent. 1,3-Cyclohexadiene is used as a hydrogen donor in transfer hydrogenation. It is used in the conversion to benzene. It is useful in the study of proteomics research. 1,3-Cyclohexadiene can undergo:C-C coupling with aromatic alcohols via iridium-catalyzed hydrogen auto-transfer and with aldehydes via transfer hydrogenation mediated by isopropanol to form carbonyl addition products.Living anionic polymerization with n-BuLi/TMEDA system to form polycyclohexadiene.Platinum-catalyzed silaboration to form (1R,4S)-1-(dimethylphenylsilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclohexene.Aerobic palladium-catalyzed 1,4-diacetoxylation in the presence of cobalt tetra(hydroquinone)porphyrin as an electron transfer reagent.

Technology Process of 1,3-Cyclohexadiene

There total 5 articles about 1,3-Cyclohexadiene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1,3,5-hexatriene (2235-12-3) → cyclohexa-1,3-diene radical cation (592-57-4) + 1,4-cyclohexadiene radical cation (628-41-1) + trans-1,3,5-hexatriene radical cation (62015-34-3) + (Z)-1,3,5-hexatriene radical cation (62015-35-4)

Guidance literature:

In dichloromethane; at -253.2 ℃; Irradiation; electronic spectra of the produced radical mixture; the radicals were investigated;

DOI:10.1021/j150657a011

Reference yield:

cyclohexa-1,4-diene (1165952-92-0) → cyclohexa-1,3-diene radical cation (592-57-4) + 1,4-cyclohexadiene radical cation (628-41-1) + trans-1,3,5-hexatriene radical cation (62015-34-3) + (Z)-1,3,5-hexatriene radical cation (62015-35-4)

Guidance literature:

In dichloromethane; at -253.2 ℃; Irradiation; electronic spectra of the produced radical mixture; the radicals were investigated;

DOI:10.1021/j150657a011

Reference yield:

cyclohexa-1,3-diene (1165952-91-9) → cyclohexa-1,3-diene radical cation (592-57-4) + 1,4-cyclohexadiene radical cation (628-41-1) + trans-1,3,5-hexatriene radical cation (62015-34-3) + (Z)-1,3,5-hexatriene radical cation (62015-35-4)

Guidance literature:

In dichloromethane; at -253.2 ℃; Irradiation; electronic spectra of the produced radical mixture; the radicals were investigated;

DOI:10.1021/j150657a011

upstream raw materials:

3-methoxycyclohexene

1,3,5-hexatriene

bicyclo{3.1.0}hex-2-ene

cyclohexa-1,4-diene

Refernces

• 1、 Rabasco, John J.,Kass, Steven R.. "The gas-phase elimination reaction of 3-methoxycyclohexene: Regiochemistry". . p. 4077 - 4080. Retrieved 2007/10/02.