Cycloheptanone

Cycloheptanone
Names
	IUPAC name Cycloheptanone
	Other names Suberone
Identifiers
CAS Number	502-42-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL18607 ;
ChemSpider	9971 ;
ECHA InfoCard	100.007.216
EC Number	207-937-6;
PubChem CID	10400;
UNII	QH80295937 ;
CompTox Dashboard (EPA)	DTXSID8060113 ;
	InChI InChI=1S/C7H12O/c8-7-5-3-1-2-4-6-7/h1-6H2 Key: CGZZMOTZOONQIA-UHFFFAOYSA-N ;
	SMILES O=C1CCCCCC1;
Properties
Chemical formula	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]
Solubility in water	Insoluble
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H302, H318
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+312, P303+361+353, P305+351+338, P310, P330, P370+378, P403+235, P501
Flash point	56 °C (133 °F; 329 K)[2]
Related compounds
Related cyclic ketones	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

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]

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References

The Merck Index, 11th Edition, 2728
Cycloheptanone at Sigma-Aldrich
Thorpe, T. E. (1912). A Dictionary of Applied Chemistry. LCCN 12009914.
Siegel, H.; Eggersdorfer, M. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077.CS1 maint: multiple names: authors list (link)
Dauben, H. J. Jr.; Ringold, H. J.; Wade, R. H.; Pearson, D. L.; Anderson, A. G. Jr. (1954). "Cycloheptanone". Organic Syntheses. 34: 19.CS1 maint: multiple names: authors list (link); Collective Volume, 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.CS1 maint: multiple names: authors list (link)
"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.

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[Merck-1] The Merck Index, 11th Edition, 2728

[Aldrich-2] Cycloheptanone at Sigma-Aldrich

[3] Thorpe, T. E. (1912). A Dictionary of Applied Chemistry. LCCN 12009914.

[ketones-4] Siegel, H.; Eggersdorfer, M. "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a15_077.CS1 maint: multiple names: authors list (link)

[organic_syntheses-5] Dauben, H. J. Jr.; Ringold, H. J.; Wade, R. H.; Pearson, D. L.; Anderson, A. G. Jr. (1954). "Cycloheptanone". Organic Syntheses. 34: 19.CS1 maint: multiple names: authors list (link); Collective Volume, 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.CS1 maint: multiple names: authors list (link)

[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.