Cycloheptanone

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Cycloheptanone
IUPAC name

Cycloheptanone

Other names

Suberone

Identifiers
CAS number 502-42-1 YesY
PubChem 10400
ChemSpider 9971 YesY
ChEMBL CHEMBL18607 YesY
Jmol-3D images Image 1
Properties
Molecular formula C7H12O
Molar mass 112.17 g mol−1
Appearance Colorless liquid
Density 0.949 g/cm3 (20 °C)[1]
Boiling point 179–181 °C[1]
Solubility in water Insoluble
Hazards
R-phrases R41[2]
S-phrases S23 S24/25 S26 S39[2]
Flash point 56 °C[2]
Related compounds
Related cyclic ketones Cyclohexanone, Cyclooctanone, Tropinone
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 destructive distillation 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 has no direct applications, but is a precursor to other compounds. Bencyclane, a spasmolytic agent and vasodilator is produced from it, for example.[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. ↑ 1.0 1.1 The Merck Index, 11th Edition, 2728
  2. ↑ 2.0 2.1 2.2 Cycloheptanone at Sigma-Aldrich
  3. ↑ Thorpe, T. E.; A dictionary of applied chemistry. 1912.
  4. ↑ 4.0 4.1 Siegel, H.; Eggersdorfer, M. (2005), "Ketones", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a15_077 
  5. ↑ 5.0 5.1 Hyp J. Dauben, Jr., Howard J. Ringold, Robert H. Wade, David L. Pearson, and Arthur G. Anderson, Jr. (1963), "Cycloheptanone", Org. Synth. ; Coll. Vol. 4: 221 
  6. ↑ Cornils, B.; Lappe, P. (2005), "Dicarboxylic Acids, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a08_523.pub2 
  7. ↑ Dicarboxylic Acids. http://www.cyberlipid.org/fa/acid0004.htm
  8. ↑ Lemiere, G. L.; Alderweireldt, F. C.; Voets, J. P.; "Reduction of cycloalkanones by several microorganisms" Zeitschrift für Allg. Mikrobiologie, 1975. 15 (2), pp 89-92. doi:10.1002/jobm.19750150204
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