1,4-Cyclohexanedione

1,4-Cyclohexanedione^[1]
	Chemical structure of Cyclohexanedione
Names
	Preferred IUPAC name Cyclohexane-1,4-dione
Identifiers
CAS Number	637-88-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	774152
ChEBI	CHEBI:28286 ;
ChemSpider	11995 ;
ECHA InfoCard	100.010.279
EC Number	211-306-0;
Gmelin Reference	101292
KEGG	C08063 ;
PubChem CID	12511;
UNII	BJS27Z99AM ;
CompTox Dashboard (EPA)	DTXSID6060929 ;
	InChI InChI=1S/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2 Key: DCZFGQYXRKMVFG-UHFFFAOYSA-N ; InChI=1/C6H8O2/c7-5-1-2-6(8)4-3-5/h1-4H2 Key: DCZFGQYXRKMVFG-UHFFFAOYAA;
	SMILES C1CC(=O)CCC1=O;
Properties
Chemical formula	C6H8O2
Molar mass	112.128 g·mol−1
Appearance	White solid
Melting point	77 to 78.5 °C (170.6 to 173.3 °F; 350.1 to 351.6 K)
Boiling point	130 to 133 °C (266 to 271 °F; 403 to 406 K) (20 mmHg)
Solubility in water	Very
Solubility	Soluble in ethanol. Insoluble in diethyl ether.
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point	132 °C (270 °F; 405 K)
	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

1,4-Cyclohexanedione is an organic compound with the formula (CH₂)₄(CO)₂. This white solid is one of the three isomeric cyclohexanediones. This particular diketone is used as a building block in the synthesis of more complex molecules.

Preparation

1,4-Cyclohexanedione is prepared in two steps from diesters of succinic acid. Specifically under basic conditions, the diethyl succinate condenses to give the cyclohexenediol derivative diethylsuccinoylsuccinate. This intermediate can be hydrolysed and decarboxylated to afford the desired dione.^[2]

This dione condenses with malononitrile to give an intermediate that can be dehydrogenated to tetracyanoquinodimethane (TCNQ).^[3]

Reactions & Uses

Protection of one of the carbonyl groups with ethylene glycol affords 1,4-cyclohexanedione monoethylene glycol ketal aka 1,4-Dioxaspiro[4.5]decan-8-one [4746-97-8].^[4]^[5] This compound is useful because it finds application in the synthesis of Ramatroban, Ciclindole, Flucindole, LY-344864 [1217756-94-9], Frovatriptan, Epibatidine,^[6]^[7] Quinelorane,^[8] Bromadol,^[9]^[10] & C-8813.

References

^ MSDS for 1,4-Cyclohexanedione
^ Nielsen, Arnold T.; Carpenter, Wayne R. (1965). "1,4-Cyclohexanedione". Organic Syntheses. 45: 25. doi:10.15227/orgsyn.045.0025.
^ Strittmatter, Harald; Hildbrand, Stefan; Pollak, Peter (2007). "Malonic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_063.pub2. ISBN 978-3-527-30673-2.
^ 孙玉亮, et al. CN109503545 (2019 to Hebei caike New Material Technology Co.,Ltd.).
^ 王淑梅, et al. CN111039917 (2020 to Tsaker Chemical Zhangzhou Co ltd).
^ Hassner, A.; Belostotskii, A. M. (March 1995). "A simple method of preparation of 7-alkyl-7-azabicyclo[2.2.1]heptanes". Tetrahedron Letters. 36 (10): 1709–1712. doi:10.1016/0040-4039(95)00051-D.
^ Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Marshall, V. P. (1 April 1997). "Microbiological Oxygenation of Bridgehead Azabicycloalkanes". The Journal of Organic Chemistry. 62 (7): 2244–2251. doi:10.1021/jo962192f.
^ Doll, M. K.-H.; Nichols, D. E.; Kilts, J. D.; Prioleau, C.; Lawler, C. P.; Lewis, M. M.; Mailman, R. B. (1 March 1999). "Synthesis and Dopaminergic Properties of Benzo-Fused Analogues of Quinpirole and Quinelorane". Journal of Medicinal Chemistry. 42 (5): 935–940. doi:10.1021/jm9804533.
^ Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Stephan Wnendt, U.S. patent 7,183,436 (2007 to Gruenenthal Gmbh).
^ Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Babette-Yvonne Koegel, U.S. patent 7,211,694 (2007 to Gruenenthal Gmbh).

[1] MSDS for 1,4-Cyclohexanedione

[OS-2] Nielsen, Arnold T.; Carpenter, Wayne R. (1965). "1,4-Cyclohexanedione". Organic Syntheses. 45: 25. doi:10.15227/orgsyn.045.0025.

[UllMal-3] Strittmatter, Harald; Hildbrand, Stefan; Pollak, Peter (2007). "Malonic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_063.pub2. ISBN 978-3-527-30673-2.

[4] 孙玉亮, et al. CN109503545 (2019 to Hebei caike New Material Technology Co.,Ltd.).

[5] 王淑梅, et al. CN111039917 (2020 to Tsaker Chemical Zhangzhou Co ltd).

[6] Hassner, A.; Belostotskii, A. M. (March 1995). "A simple method of preparation of 7-alkyl-7-azabicyclo[2.2.1]heptanes". Tetrahedron Letters. 36 (10): 1709–1712. doi:10.1016/0040-4039(95)00051-D.

[7] Davis, C. R.; Johnson, R. A.; Cialdella, J. I.; Liggett, W. F.; Mizsak, S. A.; Marshall, V. P. (1 April 1997). "Microbiological Oxygenation of Bridgehead Azabicycloalkanes". The Journal of Organic Chemistry. 62 (7): 2244–2251. doi:10.1021/jo962192f.

[8] Doll, M. K.-H.; Nichols, D. E.; Kilts, J. D.; Prioleau, C.; Lawler, C. P.; Lewis, M. M.; Mailman, R. B. (1 March 1999). "Synthesis and Dopaminergic Properties of Benzo-Fused Analogues of Quinpirole and Quinelorane". Journal of Medicinal Chemistry. 42 (5): 935–940. doi:10.1021/jm9804533.

[9] Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Stephan Wnendt, U.S. patent 7,183,436 (2007 to Gruenenthal Gmbh).

[10] Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Babette-Yvonne Koegel, U.S. patent 7,211,694 (2007 to Gruenenthal Gmbh).

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