592-57-4 Usage
Chemical Properties
clear colorless to light yellow liquid
Uses
Different sources of media describe the Uses of 592-57-4 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.
Preparation
1,3-Cyclohexadiene has been prepared by dehydration of cyclohexen-3-ol, by pyrolysis at 540° of the diacetate of cyclohexane-1,2-diol, by dehydrobromination with quinoline of 3-bromocyclohexene, by treating the ethyl ether of cyclohexen-3-ol with potassium bisulfate, by heating cyclohexene oxide with phthalic anhydride, by treating cyclohexane-1,2-diol with concentrated sulfuric acid, by treatment of 1,2-dibromocyclohexane with tributylamine, with sodium hydroxide in ethylene glycol, and with quinoline, and by treatment of 3,6-dibromo-cyclohexene with sodium.
Purification Methods
Distil the diene from NaBH4 or Na under N2 and collect it in a trap cooled in Dry Ice. It is highly flammable. [Marvel & Martell, J Am Chem Soc 81 450 1959, Beilstein 5 IV 382.]
Check Digit Verification of cas no
The CAS Registry Mumber 592-57-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 2 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 592-57:
(5*5)+(4*9)+(3*2)+(2*5)+(1*7)=84
84 % 10 = 4
So 592-57-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2
592-57-4Relevant articles and documents
ESR study of radical cations from γ-irradiation of bicyclo[3.1.0]hex-2-ene in freon matrices
Faucitano,Buttafava,Martinotti,Sustmann,Korth
, p. 2223 - 2226 (2007/10/02)
Bicyclo[3.1.0]hex-2-ene radical cation, generated by γ-irradiation of the parent compounds in freon matrices at 77 K, undergoes ring opening to the 1,3-cyclohexadiene radical cation, In CF2ClCFCl2 matrix both radical cations also undergo deprotonation to the corresponding neutral radicals.
Photochemical Rearrangements of C6H8, C7H10, and C8H12 Radical Cations in Solid Argon at 20 K
Kelsall, Benuel J.,Andrews, Lester
, p. 2723 - 2729 (2007/10/02)
C6H8 radical cations have been produced by matrix photoionization techniques and trapped in solid argon.Electronic spectra show that two different types of products are formed; a conjugated diene cation with strong and weak absorption between 30000 and 20000 cm-1 and conjugated triene cations with a strong absorption between 28000 and 22000 cm-1 and weak absorptions between 18000 and 14000 cm-1.With selective photolysis in the high-energy bands, the conjugated triene cation geometric isomers were interconverted while the cyclic diene cations were ring opened to give conjugated triene cations.Similar experiments with cyclic and bicyclic C7H10 cations gave three conjugated heptatriene cation conformers, and cyclic C8H12 cations yielded a number of conjugated octatriene cation isomers.
