592-57-4 Usage
Description
1,3-Cyclohexadiene is a clear colorless to light yellow liquid that is known for its versatile chemical properties and potential applications in various industries.
Uses
1. Used in Chemical Synthesis:
1,3-Cyclohexadiene is used as a key intermediate in the synthesis of various organic compounds due to its ability to undergo multiple chemical reactions. It is used as a hydrogen donor in transfer hydrogenation, facilitating the formation of carbonyl addition products with aldehydes and aromatic alcohols via iridium-catalyzed hydrogen auto-transfer and transfer hydrogenation mediated by isopropanol.
2. Used in Polymer Industry:
In the polymer industry, 1,3-Cyclohexadiene is used in living anionic polymerization with the n-BuLi/TMEDA system to form polycyclohexadiene, which has potential applications in the production of polymers with specific properties.
3. Used in Pharmaceutical Industry:
1,3-Cyclohexadiene is used in the platinum-catalyzed silaboration process to form (1R,4S)-1-(dimethylphenylsilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-cyclohexene, which can be further utilized in the synthesis of pharmaceutical compounds.
4. Used in Research and Development:
1,3-Cyclohexadiene is useful in the study of proteomics research, where it can be employed as a reagent or a starting material for the development of new methodologies and techniques.
5. Used in Conversion to Benzene:
1,3-Cyclohexadiene is also used in the conversion to benzene, which is a fundamental building block in the chemical industry with a wide range of applications, including the production of plastics, resins, synthetic fibers, and detergents.
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.
