Cycloheptanone
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| Names | |
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| Preferred IUPAC name
Cycloheptanone | |
| Other names
Suberone
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.216 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C7H12O | |
| Molar mass | 112.172 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.949 g/cm3 (20 °C)[1] |
| Boiling point | 179 to 181 °C (354 to 358 °F; 452 to 454 K)[1] |
| Insoluble | |
| Hazards | |
| GHS labelling: | |
  
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| Danger | |
| H226, H302, H318 | |
| P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P312, P303+P361+P353, P305+P351+P338, P310, P330, P370+P378, P403+P235, P501 | |
| Flash point | 56 °C (133 °F; 329 K)[2] |
| Related compounds | |
Related cyclic ketones
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Cyclohexanone, Cyclooctanone, Tropinone |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cycloheptanone, (CH2)6CO, is a cyclic ketone also referred to as suberone. It is a colourless volatile liquid. Cycloheptanone is used as a precursor for the synthesis of pharmaceuticals.
Synthesis
In 1836, French chemist Jean-Baptiste Boussingault first synthesized cycloheptanone from the calcium salt of dibasic suberic acid. The ketonization of calcium suberate yields calcium carbonate and suberone:[3]
- Ca(O2C(CH2)6CO2) → CaCO3 + (CH2)6CO
Cycloheptanone is still produced by the cyclization and decarboxylation of suberic acid or suberic acid esters. This reaction is typically conducted in the gas phase at 400–450 °C over alumina doped with zinc oxide or cerium oxide.[4]
Cycloheptanone is also produced by the reaction of cyclohexanone with sodium ethoxide and nitromethane. The resulting sodium salt of 1-(nitromethyl)cyclohexanol is added to acetic acid and shaken with hydrogen gas in the presence of W-4 Raney nickel catalyst. Sodium nitrite and acetic acid are then added to give cycloheptanone.[5]
Cycloheptanone is also prepared by ring expansion of cyclohexanone with diazomethane as the methylene source.[5]
Uses and reactions
Cycloheptanone is a precursor to bencyclane, a spasmolytic agent and vasodilator.[4] Pimelic acid is produced by the oxidative cleavage of cycloheptanone.[6] Dicarboxylic acids such as pimelic acid are useful for the preparation of fragrances and certain polymers.[7]
Several microorganisms, including Mucor plumbeus, Mucor racemosus, and Penicillium chrysogenum, have been found to reduce cycloheptanone to cycloheptanol. These microorganisms have been investigated for use in certain stereospecific enzymatic reactions.[8]
References
- ^ a b The Merck Index, 11th Edition, 2728
- ^ Cycloheptanone at Sigma-Aldrich
- ^ Thorpe, T. E. (1912). A Dictionary of Applied Chemistry. LCCN 12009914.
- ^ a b Siegel, H.; Eggersdorfer, M. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077. ISBN 978-3527306732.
- ^ a b Dauben, H. J. Jr.; Ringold, H. J.; Wade, R. H.; Pearson, D. L.; Anderson, A. G. Jr. (1954). "Cycloheptanone". Organic Syntheses. 34: 19; Collected Volumes, vol. 4, p. 221.
- ^ Cornils, B.; Lappe, P. "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.pub2. ISBN 978-3527306732.
- ^ "Dicarboxylic Acids". cyberlipids.org. Archived from the original on 2011-09-07. Retrieved 2011-04-26.
- ^ Lemiere, G. L.; Alderweireldt, F. C.; Voets, J. P. (1975). "Reduction of cycloalkanones by several microorganisms". Zeitschrift für Allgemeine Mikrobiologie. 15 (2): 89–92. doi:10.1002/jobm.19750150204.