1,3-cyclohexadiene
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| Names | |||
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IUPAC name
Cyclohexa-1,3-diene
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| Other names
1,3-Cyclohexadiene, 1,2-Dihydrobenzene, 1,3-CHD
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| Identifiers | |||
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3D model (Jmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.008.878 | ||
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PubChem CID
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| RTECS number | GU4702350 | ||
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| Properties | |||
| C6H8 | |||
| Molar mass | 80.13 g/mol | ||
| Appearance | Colorless liquid | ||
| Density | 0.841 g/cm3 | ||
| Melting point | −98 °C (−144 °F; 175 K) | ||
| Boiling point | 80 °C (176 °F; 353 K) | ||
| -48.6·10−6 cm3/mol | |||
| Hazards | |||
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EU classification (DSD)
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Flammable (F) | ||
| R-phrases | R11 | ||
| S-phrases | S9 S16 S29 S33 | ||
| Flash point | 26 °C (79 °F; 299 K) c.c. | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |||
1,3-Cyclohexadiene is an organic compound with the formula (CH2)2(CH)4. It is a colorless, flammable liquid. Its refractive index is 1.475 (20 °C, D). A naturally occurring derivative of 1,3-cyclohexadiene is terpinene, a component of pine oil.
Cyclohexadiene is prepared by the dehydrobromination of 1,2-dibromocyclohexane:
1,3-Cyclohexadiene can also be prepared by the electrocyclic reaction from 1,3,5-hexatriene either or at temperatures above 110 °C.
Useful reactions of this diene are cycloadditions, such as the Diels-Alder reaction.
1,3-Cyclohexadiene could in principle be used as a hydrogen donor in transfer hydrogenation, since its conversion to benzene + hydrogen is exothermic by about 25 kJ/mol (gas phase).
Compared with its isomer 1,4-cyclohexadiene, 1,3-cyclohexadiene is about 8.5 kJ/mol more stable.
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