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| 1,3-CYCLOHEXADIENE Basic information |
| 1,3-CYCLOHEXADIENE Chemical Properties |
| Melting point | -98 °C | | Boiling point | 80 °C (lit.) | | density | 0.841 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.474(lit.) | | Fp | −2 °F | | storage temp. | 2-8°C | | form | Liquid | | color | Clear colorless to light yellow | | Water Solubility | Slightly miscible with methanol. Immiscible with water. | | BRN | 506024 | | CAS DataBase Reference | 592-57-4(CAS DataBase Reference) | | EPA Substance Registry System | 1,3-Cyclohexadiene (592-57-4) |
| Hazard Codes | F | | Risk Statements | 11-10-37 | | Safety Statements | 9-16-29-33 | | RIDADR | UN 3295 3/PG 2 | | WGK Germany | 3 | | RTECS | GU4702350 | | F | 9 | | TSCA | Yes | | HazardClass | 3 | | PackingGroup | II | | HS Code | 29021990 |
| 1,3-CYCLOHEXADIENE Usage And Synthesis |
| Chemical Properties | clear colorless to light yellow liquid | | 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. | | Uses | 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. | | 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.
| | 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.] |
| 1,3-CYCLOHEXADIENE Preparation Products And Raw materials |
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