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).
	verify (what is ?)
	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]

gollark: I figure it's not hugely useful linking to all the many, many individual function documentation pages. So maybe only the important functions, important *APIs*, or more freeform documentation for other stuff.

gollark: A link to the main page is useful, Yemmel's project idea list, maybe other things?

gollark: The CC:T wiki?

gollark: That is an oddly specific scenario. And you can just check the online version *now*.

gollark: I check Wikipedia rather than using the (surprisingly small) database dump, partly because the database dump is text-only and the software for viewing it is lacking, and partly because there's just no particular reason to not use the online one.

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.