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1,4-Cyclohexanedione 
Summary
1,4-Cyclohexanedione is an organic compound with the formula (CH2)4(CO)2. This white solid is one of the three isomeric cyclohexanediones. This particular diketone is used as a building block in the synthesis of more complex molecules.
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| Names | |
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| Preferred IUPAC name
Cyclohexane-1,4-dione | |
| Identifiers | |
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3D model (JSmol)
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| 3DMet |
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| 774152 | |
| ChEBI |
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| ChemSpider |
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| ECHA InfoCard | 100.010.279 |
| EC Number |
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| 101292 | |
| KEGG |
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PubChem CID
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| UNII |
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CompTox Dashboard (EPA)
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| Properties | |
| C6H8O2 | |
| Molar mass | 112.128 g·mol−1 |
| Appearance | White solid |
| Melting point | 77 to 78.5 °C (170.6 to 173.3 °F; 350.1 to 351.6 K) |
| Boiling point | 130 to 133 °C (266 to 271 °F; 403 to 406 K) (20 mmHg) |
| Very | |
| Solubility | Soluble in ethanol. Insoluble in diethyl ether. |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
| Flash point | 132 °C (270 °F; 405 K) |
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
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Preparation edit
1,4-Cyclohexanedione is prepared in two steps from diesters of succinic acid. Specifically under basic conditions, the diethyl succinate condenses to give the cyclohexenediol derivative diethylsuccinoylsuccinate. This intermediate can be hydrolysed and decarboxylated to afford the desired dione.[2]
This dione condenses with malononitrile to give an intermediate that can be dehydrogenated to tetracyanoquinodimethane (TCNQ).[3]
References edit
- ^ MSDS for 1,4-Cyclohexanedione
- ^ Nielsen, Arnold T.; Carpenter, Wayne R. (1965). "1,4-Cyclohexanedione". Organic Syntheses. 45: 25. doi:10.15227/orgsyn.045.0025.
- ^ Strittmatter, Harald; Hildbrand, Stefan; Pollak, Peter (2007). "Malonic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_063.pub2. ISBN 978-3527306732.