1,4-Cyclohexanedione

1,4-Cyclohexanedione Basic information
Product Name:1,4-Cyclohexanedione
Synonyms:1,4-Dioxocyclohexane;Tetrahydroquinone;TETRAHYDRO-P-BENZOQUINONE;Cyclohexan-1,4-dione 98%;1,4-CYCHEXANEDIONE;Cyclohexan-1,4-dione;1,4-Cyclohexanedione,98%;1,4-CYCLOHEXANDIONE
CAS:637-88-7
MF:C6H8O2
MW:112.13
EINECS:211-306-0
Product Categories:C3 to C6;Carbonyl Compounds;Ketones;Building Blocks;C3 to C6;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;fine chemicals;ketone;Pharmaceutical Intermediate
Mol File:637-88-7.mol
1,4-Cyclohexanedione Structure
1,4-Cyclohexanedione Chemical Properties
Melting point 77-78.5 °C (lit.)
Boiling point 112 °C (19.5026 mmHg)
density 1.0861
refractive index 1.4570 (estimate)
Fp 132 °C
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Soluble in methanol and ethanol.
form Crystalline Powder or Flakes
color Light yellow to yellow or beige
BRN 774152
Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
LogP-0.910 (est)
CAS DataBase Reference637-88-7(CAS DataBase Reference)
NIST Chemistry Reference1,4-Cyclohexanedione(637-88-7)
EPA Substance Registry System1,4-Cyclohexanedione (637-88-7)
Safety Information
Hazard Codes Xi
Safety Statements 22-24/25
WGK Germany 3
8
Hazard Note Irritant
TSCA Yes
HS Code 29142900
MSDS Information
ProviderLanguage
1,4-Cyclohexanedione English
SigmaAldrich English
ACROS English
ALFA English
1,4-Cyclohexanedione Usage And Synthesis
Chemical Propertiestan or yellow crystalline powder
Uses1,4-Cyclohexanedione is used in the preparation of 1,4 benzoquinone and bromoorganics. It is also used to study the influence of visible light on the bromate-1,4-cyclohexanedione-ferroin oscillating reaction. It plays a vital role in pharmaceuticals, plant growth regulator and as a conducting material.
DefinitionChEBI: 1,4-Cyclohexanedione is a cyclohexanedione with oxo substituents at positions 1 and 4.
PreparationSynthesis of 1,4-cyclohexanedione: put diethyl succinylsuccinate into a flask, add a mixture of concentrated sulfuric acid, water and ethanol, reflux in oil solution for 5 days, cool, and neutralize to pH with ammonia water = 8; then extract 4 times with chloroform, and recover the chloroform to obtain the crude product; then the crude product is subjected to vacuum distillation, and the distillate is poured into cold petroleum ether, filtered, and air-dried to obtain 1,4-cyclohexanedi Ketone Products.
Synthesis Reference(s)Synthesis, p. 165, 1981 DOI: 10.1055/s-1981-29377
General Description1,4-Cyclohexanedione(CHD) undergoes uncatalyzed oscillatory reactions during oxidation by acidic bromate in nitric acid and sulphuric acid solution. It reacts with acidic bromate to form 1,4-dihydroxybenzene which on further oxidation and bromination yields 1,4-benzoquinone and bromoorganics.
PharmacologyThe cyclohexanedione (CHD) herbicides inhibit fatty acid synthesis in plants by interfering with the activity of the enzyme Acetyl-Coenzyme A Carboxylase (ACCase). ACCase-inhibiting herbicides provide excellent control of grass weeds in dicotyledonous and some grass crops. A less-sensitive ACCase mediates the intrinsic resistance of dicotyledonous plants to the AOPP and CHD herbicides (34,35). Although grasses are target species of this group of herbicides, not all are equally affected, and sensitivity differences can occur between varieties or even within a genus.
DIETHYL 2,5-DIOXOBICYCLO[2.2.2]OCTANE-1,4-DICARBOXYLATE 2,3,4A,5,8,8A-HEXAHYDRO-(1,4)NAPHTHOQUINONE AURORA KA-2969 AKOS BBS-00002047 1,9,10,11-TETRACHLORO-12,12-DIMETHOXY-4-METHYL-5-OXATETRACYCLO[7.2.1.0(2,8).0(4,6)]DODEC-10-ENE-3,7-DIONE (4AR,8AS)-2,2,4A-TRIMETHYLOCTAHYDROCYCLOBUTA[C]INDENE-5,8-DIONE AURORA KA-2971 5-OXATETRACYCLO[7.2.1.0(2,8).0(4,6)]DODEC-10-ENE-3,7-DIONE AURORA KA-2970 CYCLOHEXANEHEXONE HYDRATE Diethyl succinosuccinate 1,9,10,11-TETRACHLORO-12,12-DIMETHOXY-5-OXATETRACYCLO[7.2.1.0(2,8).0(4,6)]DODEC-10-ENE-3,7-DIONE HEXAKETOCYCLOHEXANE OCTAHYDRATE TRIQUINOLYL 2,5-BIS(TRIFLUOROACETYL)CYCLOHEXANE-1,4-DIONE Bicyclo[2.2.2]octane-2,5-dione SALOR-INT L166049-1EA 4-METHYL-5-OXATETRACYCLO[7.2.1.0(2,8).0(4,6)]DODEC-10-ENE-3,7-DIONE

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