Cycloheptanone

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.

Cycloheptanone
Names
Preferred IUPAC name
Cycloheptanone
Other names
Suberone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.216
EC Number
  • 207-937-6
UNII
  • InChI=1S/C7H12O/c8-7-5-3-1-2-4-6-7/h1-6H2 checkY
    Key: CGZZMOTZOONQIA-UHFFFAOYSA-N checkY
  • O=C1CCCCCC1
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:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
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
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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Infobox references

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
  1. The Merck Index, 11th Edition, 2728
  2. Cycloheptanone at Sigma-Aldrich
  3. Thorpe, T. E. (1912). A Dictionary of Applied Chemistry. LCCN 12009914.
  4. Siegel, H.; Eggersdorfer, M. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077.
  5. Dauben, H. J. Jr.; Ringold, H. J.; Wade, R. H.; Pearson, D. L.; Anderson, A. G. Jr. (1954). "Cycloheptanone". Organic Syntheses. 34: 19.; Collective Volume, vol. 4, p. 221
  6. Cornils, B.; Lappe, P. "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.pub2.
  7. "Dicarboxylic Acids". cyberlipids.org. Archived from the original on 2011-09-07. Retrieved 2011-04-26.
  8. 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.
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