Conditions | Yield |
---|---|
With aluminium trichloride; zinc In tetrahydrofuran for 0.4h; Ambient temperature; | 100% |
With formic acid In toluene at 120℃; for 10h; Inert atmosphere; chemoselective reaction; | 57% |
With hydrogen; tetra-(n-butyl)ammonium iodide In water at 110℃; under 15001.5 Torr; for 24h; chemoselective reaction; | 57% |
With ruthenium; hydrogen at 80℃; under 37503.8 Torr; for 1h; Reagent/catalyst; Ionic liquid; chemoselective reaction; |
1,4-cyclohexanedione bis(dimethyl acetal)
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
In 1,4-dioxane; water; dimethyl sulfoxide for 12h; Heating; | 98.2% |
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In neat (no solvent) at 20℃; for 1h; Milling; | 97% |
With ruthenium(IV) oxide; sodium dihydrogenphosphate; sodium chloride In water at 10 - 15℃; electrooxidation; | 94% |
With m-iodosylbenzoic acid; ruthenium trichloride In water; acetonitrile at 20℃; for 10h; | 84% |
Conditions | Yield |
---|---|
With barium(II) chloride In water at 19.85 - 179.85℃; under 7575.61 Torr; for 0.666667h; | 96% |
With CuCl2*2H2O In acetonitrile for 0.5h; Ambient temperature; | 95% |
With trifluoroacetic acid In dichloromethane at 25℃; for 12h; | 90% |
Conditions | Yield |
---|---|
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 6h; Oxidation; | A 1% B 93% |
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 2h; Oxidation; | A 78% B 10% |
With 2O34W9Zn(12-)*W(6+)*3Zn(2+)*2H2O; dihydrogen peroxide In water; acetonitrile at 135℃; under 2250.23 Torr; for 0.25h; Microwave irradiation; | A n/a B 58% |
3,5-dimethyl-1H-pyrazole
A
cyclohexanedione monoethylene ketal
B
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
In dichloromethane; ethyl acetate | A 91% B n/a |
1,4-Cyclohexandion-bis-(dimethylhydrazon)
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII) In acetic acid; acetonitrile at 0 - 20℃; Product distribution; oxidative cleavage; | 88% |
4-hydroxycyclohexanone
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane for 2h; Ambient temperature; | 87% |
(Z,Z)-1,4-Cyclohexandion-bis
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With hydrogenchloride In dichloromethane for 12h; Ambient temperature; | 87% |
Conditions | Yield |
---|---|
With tetrachlorosilane In dichloromethane at 20℃; for 0.5h; | 85% |
Conditions | Yield |
---|---|
In methanol Irradiation (UV/VIS); anaerobic irradiation 1h with visible light at 20°C; analyzing products by GLC; | A 69% B 19% |
In water Irradiation (UV/VIS); anaerobic irradiation 1h with visible light in single-compartment vesicle of N,N-dihexadecyl-Nα-(6-(trimethylammonio)hexanoyl)-L-alaninamide bromide at 20°C; phosphate-borate buffer; analyzing products by GLC; | A 19% B 67% |
In benzene Irradiation (UV/VIS); anaerobic irradiation 1h with visible light at 20°C; analyzing products by GLC; | A 57% B 28% |
Conditions | Yield |
---|---|
With hydrogenchloride; tetrakis(tetrabutylammonium)decatungstate(VI); oxygen In dichloromethane; water; acetonitrile at 20℃; for 0.75h; Flow reactor; Irradiation; | 67% |
With methanol; dihydrogen peroxide; vanadia | |
With water at 20℃; under 750.075 Torr; for 48h; Catalytic behavior; Electrolysis; | Ca.97%Spectr. |
1,4,9,12-Tetraoxa-dispiro[4.2.4.2]tetradecane
A
cyclohexanedione monoethylene ketal
B
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With formaldehyd; silica gel; iron(III) chloride at 20℃; for 0.416667h; | A 58% B 22 % Chromat. |
2,3-dioxabicyclo<2.2.2>octane
A
ethene
B
butanedial
C
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
at 450℃; under 0.001 Torr; Product distribution; Mechanism; | A n/a B 56% C 42% |
Conditions | Yield |
---|---|
at 450℃; | A 56% B 42% |
1,1,4,4-tetramethoxycyclohexa-2,5-diene
A
1,4-cyclohexanedione bis(dimethyl acetal)
B
4-methoxy-3-cyclohexenone dimethyl acetal
C
1,4-Cyclohexanedione
D
1,4-dimethoxybezene
Conditions | Yield |
---|---|
With sodium methylate In methanol electrolysis cathodic reaction (R-Ni powder cathode, Pt plate anode, 300 mA, 2.4 V); | A 45% B 24% C 6% D 24% |
2,3-dioxabicyclo<2.2.2>octane
A
butanedial
B
cis-1,4-cyclohexanediol
C
4-hydroxycyclohexanone
D
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With cobalt(II) 5,10,15,20-tetraphenylporphyrin In chloroform at 60℃; for 11h; Further byproducts given; | A 21% B 28% C 17% D 5% |
4-methoxycyclohexanone
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With calcium hypochlorite; acetic acid In water; acetonitrile at 0℃; regioselective reaction; | 20% |
Conditions | Yield |
---|---|
With H4Na12O66W19Zn5; sulfuric acid; oxygen In water at 25℃; under 750.075 Torr; for 0.75h; pH=1; Irradiation; | 14% |
Multi-step reaction with 2 steps 1: water / 48 h / 20 °C / 750.08 Torr / Electrolysis 2: water / 48 h / 20 °C / 750.08 Torr / Electrolysis View Scheme |
Conditions | Yield |
---|---|
With sulfuric acid | |
With water at 200℃; |
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
bei der Destillation des bernteinsauren Calciums; |
4-(propan-2-ylidene)cyclohexan-1-one
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With permanganate(VII) ion |
3,6-dioxo-cyclohexane-1,2-dicarbonitrile
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With sulfuric acid |
Conditions | Yield |
---|---|
With fired clay at 260℃; | |
With fired clay at 400℃; |
3,4-dihydro-2H-pyran
1,4-Cyclohexanediol
A
4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanone
B
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With jones reagent; toluene-4-sulfonic acid 1) acetone, 1 h, ice-bath cooling, 2) CH2Cl2, 30 min, rt; Yield given. Multistep reaction. Yields of byproduct given; |
2,3-dioxabicyclo<2.2.2>octane
A
cis-1,4-cyclohexanediol
B
4-hydroxycyclohexanone
C
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 60℃; for 5h; Product distribution; other reagent; | A 39 % Chromat. B 44 % Chromat. C 4 % Chromat. |
2,5-dihydroxy-1,4-benzenedicarboxylic acid
A
1,4-cyclohexanedione-2,5-dicarboxylic acid
B
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With sodium hydroxide; sodium amalgam at 0℃; for 0.5h; Yield given; |
Conditions | Yield |
---|---|
With sodium persulfate; iron(II) sulfate In water at 80℃; for 6h; Yield given. Yields of byproduct given; |
cyclohexanone
A
cyclohexenone
B
cyclohex-3-enone
C
hexanoic acid
D
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With sodium persulfate; iron(II) sulfate In water Yield given. Yields of byproduct given; |
4,5-bis(4-dodecyloxyphenylethynyl)benzene-1,2-dicarbaldehyde
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 55℃; | 100% |
benzoyl chloride
1,4-Cyclohexanedione
trans-1,4-di(phenylcarbonyl)aminocyclohexane-1,4-dinitrile
Conditions | Yield |
---|---|
Stage #1: potassium cyanide; 1,4-Cyclohexanedione With ammonium chloride In water at 20℃; Strecker reaction; Cooling with ice; Inert atmosphere; Stage #2: benzoyl chloride With potassium carbonate In tetrahydrofuran; water at 20℃; for 72h; Inert atmosphere; | 100% |
2-amino-benzenethiol
1,4-Cyclohexanedione
3H,3''H-dispiro{benzothiazole-2,1'-cyclohexane-4',2''-benzothiazole}
Conditions | Yield |
---|---|
In ethanol for 2h; Reflux; | 99% |
Conditions | Yield |
---|---|
With samarium diiodide; water In tetrahydrofuran at 20℃; | 99% |
With sodium tetrahydroborate; TiO(acac)2 In tetrahydrofuran for 0.17h; Heating; | 93% |
With sodium tetrahydroborate; Dowex1-x8 In tetrahydrofuran for 0.34h; Heating; | 90% |
2,3-diformylthiophene
1,4-Cyclohexanedione
dithieno<2,3-b><6,7-d>-9,10-anthraquinone
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water at 20℃; for 4h; Inert atmosphere; | 99% |
With potassium hydroxide In ethanol | 93% |
With potassium hydroxide In ethanol for 1h; | 92.8% |
With potassium hydroxide In ethanol at 20℃; | 84% |
With potassium hydroxide In ethanol; water |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 20℃; for 17h; Reflux; Dean-Stark; | 99% |
Conditions | Yield |
---|---|
With trimethyl orthoformate at 20℃; for 0.5h; | 98% |
Ce(3+)-mont at 25℃; for 0.5h; | 96% |
With trimethyl orthoformate at 80℃; under 6000480 Torr; for 19h; | 94% |
With oxygen at 20℃; for 16h; UV-irradiation; | 87% |
1,2-diamino-benzene
1,4-Cyclohexanedione
dispiro[2H-benzimidazole-2,1'-cyclohexane-4',2''-[2H]benzimidazole]
Conditions | Yield |
---|---|
In ethanol for 10h; Heating; | 98% |
ethane-1,2-dithiol
1,4-Cyclohexanedione
1,4-cyclohexanedione diethylenethioacetal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 6h; Reflux; | 98% |
With dimethylbromosulphonium bromide at 20℃; for 1h; | 89% |
With [silica-OSi(OMe)2C3H6(N2C3(CH3)H2)C4H8SO3H]HSO4 In water for 7h; | 89% |
(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(pyridin-2-ylsulfanyl)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With samarium diiodide In tetrahydrofuran at 20℃; for 0.0833333h; Reformatsky reaction; | 98% |
4,5-dibutylthiophene-2,3-dicarbaldehyde
1,4-Cyclohexanedione
2,3,7,8-tetrabutylanthradithiophene-5,11-dione
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 20℃; for 3h; Inert atmosphere; | 98% |
1,4-Cyclohexanedione
1,4-cyclohexanedioxime
Conditions | Yield |
---|---|
Stage #1: 1,4-Cyclohexanedione With hydroxylamine hydrochloride In water at 0 - 20℃; for 0.5h; Stage #2: With potassium carbonate In water | 98% |
Conditions | Yield |
---|---|
With C29H38AlN4O2(1+)*CF3O3S(1-) In neat (no solvent) at 20℃; for 0.25h; Catalytic behavior; Inert atmosphere; Schlenk technique; | 98% |
Conditions | Yield |
---|---|
With (S)-(-)-SEGphos; palladium diacetate; toluene-4-sulfonic acid In 5,5-dimethyl-1,3-cyclohexadiene at 85℃; for 14h; Reagent/catalyst; Solvent; Inert atmosphere; | 98% |
With (S)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(diphenylphosphine); palladium diacetate; toluene-4-sulfonic acid In 5,5-dimethyl-1,3-cyclohexadiene at 85℃; for 14h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 90 - 112℃; for 10h; Reagent/catalyst; Solvent; Dean-Stark; | 98% |
diethoxyphosphoryl-acetic acid ethyl ester
1,4-Cyclohexanedione
1,4-di(ethoxycarbonyl-methylidyne) cyclohexane
Conditions | Yield |
---|---|
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: 1,4-Cyclohexanedione In tetrahydrofuran at 20℃; for 0.5h; | 97% |
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In 1,2-dimethoxyethane at 0℃; for 1h; Stage #2: 1,4-Cyclohexanedione In 1,2-dimethoxyethane at 20℃; for 0.5h; | 50% |
cyclopenta-1,3-diene
1,4-Cyclohexanedione
1,4:5,8-dimethano-1,4,4a,5,8,8a,9a,10a-octahydroanthracene-9,10-dione
Conditions | Yield |
---|---|
In ethanol at -10 - 0℃; for 1h; Inert atmosphere; | 96.8% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 4h; Inert atmosphere; | 96% |
With potassium hydroxide In methanol; water at 0 - 64℃; for 12h; Inert atmosphere; | 86% |
With water; potassium hydroxide In ethanol at 60℃; for 4h; Inert atmosphere; | 85% |
ethylene glycol
1,4-Cyclohexanedione
cyclohexanedione monoethylene ketal
Conditions | Yield |
---|---|
With triethylmethylammonium chloride at 50℃; for 1h; Temperature; Reagent/catalyst; | 96% |
With toluene-4-sulfonic acid In benzene at 100℃; for 1.5h; | 35% |
With toluene-4-sulfonic acid In benzene for 4h; Heating; |
Conditions | Yield |
---|---|
With lithium chloride In various solvent(s) at 160 - 170℃; for 1h; | 96% |
With 1,3-dimethyl-2-imidazolidinone; lithium chloride at 165℃; for 1h; | 70% |
With lithium chloride In pyridine for 1h; Reflux; | 33% |
diethyl (2R,3R)-tartrate
1,4-Cyclohexanedione
tetraethyl (2R,3R,10R,11R)-1,4,9,12-tetraoxadispiro[4.2.48.25]tetradecane-2,3,10,11-tetracarboxylate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 30h; cyclocondensation; Heating; | 96% |
With toluene-4-sulfonic acid In toluene for 120h; Condensation; Heating; | 92% |
With boron trifluoride diethyl etherate In ethyl acetate at 0 - 20℃; | 55% |
With boron trifluoride diethyl etherate In ethyl acetate at 0℃; |
1,4-Cyclohexanedione
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); formic acid; triethylamine In acetonitrile at 20℃; | 96% |
With Candida parapsilosis ATCC 7330 whole cells In ethanol; water at 25℃; for 8h; pH=6.8; Microbiological reaction; regioselective reaction; | 63% |
With sodium tetrahydroborate In methanol at -20℃; | 60% |
With keto reductases from Lactobacillus kefir; nicotinamide adenine dinucleotide phosphate; isopropyl alcohol In aq. phosphate buffer at 30℃; for 12h; pH=7; Reagent/catalyst; pH-value; Enzymatic reaction; |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 60℃; | 96% |
Conditions | Yield |
---|---|
With orthoformic acid triethyl ester at 20℃; for 0.5h; | 96% |
Conditions | Yield |
---|---|
With iodine at 50℃; for 5h; Ionic liquid; Combinatorial reaction / High throughput screening (HTS); | 96% |
Conditions | Yield |
---|---|
With iodine at 50℃; for 4h; Ionic liquid; Combinatorial reaction / High throughput screening (HTS); | 96% |
With bis(glycerol)boric acid; bis(glycerol)boric acid at 60℃; for 0.833333h; Green chemistry; | 87% |
With 1-methyl-3-[3-(triethoxysilyl)propyl]-1H-imidazol-3-ium hydrogen sulfate, immobilized on the surface of Fe3O4SiO2 magnetic nanoparticles In ethanol for 0.333333h; Catalytic behavior; Reflux; Green chemistry; | 84% |
The Molecular Structure of 1,4-Cyclohexanedione (CAS NO.637-88-7):
Empirical Formula: C6H8O2
Molecular Weight: 112.1265
Nominal Mass: 112 Da
Average Mass: 112.1265 Da
Monoisotopic Mass: 112.052429 Da
Index of Refraction: 1.473
Molar Refractivity: 27.93 cm3
Molar Volume: 99.4 cm3
Surface Tension: 40.5 dyne/cm
Density: 1.127 g/cm3
Flash Point: 82.2 °C
Enthalpy of Vaporization: 46.32 kJ/mol
Boiling Point: 226.7 °C at 760 mmHg
Vapour Pressure: 0.0809 mmHg at 25°C
Melting Point: 76-80°C
IUPAC Name: cyclohexane-1,4-dione
Appearance: tan or yellow crystalline powder
Synonyms: 1,4-Cyclohexanedion;1,4-Dioxocyclohexane;Tetrahydroquinone;Tetrahydro-p-benzoquinone;1,4-Cyclohexandione;1,4-Tetrahydroquinone;Cyclohexane-1,4-dione;CHD
Product Categories: ketone;Pharmaceutical Intermediate;C3 to C6;Carbonyl Compounds;Ketones
1,4-Cyclohexanedione (CAS NO.637-88-7) is prepared in two steps from diesters of succinic acid. For example under basic conditions, the diethyl ester condenses to give 2,5-dicarbethoxy-1,4-cyclohexanedione. This intermediate can be hydrolysed and decarboxylated to afford the desired dione.
1,4-Cyclohexanedione (CAS NO.637-88-7) is used as a building block in the synthesis of more complex molecules.
1,4-Cyclohexanedione (CAS NO.637-88-7) is prepared in two steps from diesters of succinic acid.Under basic conditions, the diethyl ester condenses to give 2,5-dicarbethoxy-1,4-cyclohexanedione. This intermediate can be hydrolysed and decarboxylated to afford the desired dione.
Hazard Codes: Xi
Safety Statements: 22-24/25
S22:Do not breathe dust
S24/25:Avoid contact with skin and eyes
WGK Germany: 3
F: 8
Hazard Note: Irritant
HS Code: 29142900
Do not breathe the dust of 1,4-Cyclohexanedione (CAS NO.637-88-7). Avoid 1,4-Cyclohexanedione (CAS NO.637-88-7) contact with skin and with eyes.
1,4-Cyclohexanedione (CAS NO.637-88-7) is the organic compound. This colourless solid is one of the three isomeric cyclohexanediones. This particular diketone is used as a building block in the synthesis of more complex molecules.
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