Conditions | Yield |
---|---|
Stage #1: 2-methoxycyclohexanone With propyl cyanide at 47℃; for 0.833333h; Stage #2: In dimethyl sulfoxide for 1.33333h; Stage #3: With sodium nitrate; platinum(IV) chloride In dimethyl sulfoxide at 56℃; for 3h; Temperature; | 98.3% |
Conditions | Yield |
---|---|
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 2.5h; Oxidation; | A 1% B 95% |
With fluorine In acetonitrile at 20℃; Baeyer-Villiger oxidation; | A 30% B 53% |
(1R,2R)-trans-1,2-cyclohexanediol
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide In decane; acetonitrile at 65℃; for 2.5h; | 93% |
With tert.-butylhydroperoxide; thiourea S,S-dioxide In dodecane; acetonitrile at 65℃; for 4.5h; | 90% |
With tert.-butylhydroperoxide In decane; acetonitrile at 65℃; for 0.5h; | 78% |
Conditions | Yield |
---|---|
With N-methylpyrrolidine-2-one hydrotribromide; dihydrogen peroxide In acetonitrile for 0.5h; Heating; | 91% |
With tert.-butylhydroperoxide; iron(III) chloride; thymidyl acetic acid In decane; acetonitrile at 80℃; for 16h; | 80% |
With tetraphenylphosphonium monoperoxysulfate; 2-Iodobenzoic acid In 1,2-dichloro-ethane at 80℃; for 12h; | 79% |
2,2-dimethoxycyclohexanol
A
2,2-dimethoxycyclohexanone
B
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With silver | A n/a B 88.5% |
Conditions | Yield |
---|---|
With iron(III) chloride; dimethyl sulfoxide at 100℃; for 3h; | 85% |
With iodine In water; acetonitrile at 40℃; for 2h; Solvent; Temperature; | 81% |
With 2,2,6,6-tetramethylpiperidin-1-oxoammonium chloride; toluene-4-sulfonic acid | 75% |
Conditions | Yield |
---|---|
With silica gel; copper(II) nitrate In tetrachloromethane at 25℃; for 0.833333h; | 85% |
With [(hydrotris(3,5-diphenyl-pyrazol-1-yl)borate)FeII(benzilate)]; oxygen In benzene for 0.333333h; |
Conditions | Yield |
---|---|
With oxygen In benzene at 10℃; for 1h; Kinetics; Reagent/catalyst; | A 85% B 13% |
3-Chloro-N-(2-hydroxy-phenyl)-N-(6-oxo-cyclohex-1-enyl)-benzamide
A
o-phenol
B
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With silica gel In dichloromethane for 2.5h; Ambient temperature; | A 82% B 77% |
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 3.5h; Ambient temperature; | 81% |
2-(methylthio)cyclohexanone
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With CuCl2-CuO In water; acetone at 35℃; for 0.5h; | 80% |
With copper(II) oxide; copper dichloride In water; acetone at 35℃; for 0.5h; | 80% |
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 5h; Ambient temperature; | 78% |
1-(1-Ethoxy-2-oxocyclohexyl)-4-phenyl-1,2,4-triazolidin-3,5-dion
A
4-Phenylurazole
B
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With hydrogenchloride; water In 1,4-dioxane for 1.5h; Heating; | A 75% B 75% |
1,2-Cyclohexanediol
A
Adipic acid
B
cyclohexane-1,2-dione
C
cyclohexanone-2-ol
Conditions | Yield |
---|---|
With sodium bromate; sodium hydrogensulfite In dichloromethane; water; acetonitrile at 20℃; for 3h; Oxidation; | A 13% B 74% C 8% |
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 2h; Oxidation; | A 18% B 19% C 51% |
With 2O34W9Zn(12-)*W(6+)*3Zn(2+)*2H2O; dihydrogen peroxide In water; acetonitrile at 135℃; under 2250.23 Torr; for 0.25h; Microwave irradiation; |
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In dichloromethane for 5h; Ambient temperature; | 74% |
Conditions | Yield |
---|---|
With oxygen; copper(II) bis(trifluoromethanesulfonate); dimethyl sulfoxide; bismuth at 100℃; for 2h; | 74% |
Conditions | Yield |
---|---|
With pyridine; N-Bromosuccinimide In tetrachloromethane for 1.5h; Heating; | 74% |
cyclohexane-1,2-dione monooxime
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With silica gel; copper(II) nitrate In tetrachloromethane for 0.833333h; Heating; | 72% |
2-bromocyclohexanone
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With potassium fluoride; dimethyl sulfoxide at 85℃; for 5h; | 65% |
1,4,7,10-tetrathia-dispiro[4.0.4.4]tetradecane
A
6-oxospiro
B
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With water; 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate In tetrahydrofuran; dichloromethane at 23℃; | A 65% B 15% |
cis-1,2-cyclohexane
A
hexanedial
B
cyclohexane-1,2-dione
C
cyclohexanone-2-ol
Conditions | Yield |
---|---|
With oxygen; [(n-Bu)4N]3H2[IMo6O24] In acetonitrile at 80℃; under 1520.1 Torr; for 5h; | A 5% B 31% C 64% |
Conditions | Yield |
---|---|
With sulfuric acid; silica gel In dichloromethane for 24h; Ambient temperature; | 63% |
methanol
2-diazocyclohexanone
A
hexanedioic acid dimethyl ester
B
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With oxygen; methylene blue Irradiation; | A 60% B 25% |
2-diazocyclohexanone
A
hexanedioic acid dimethyl ester
B
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With oxygen; methylene blue In methanol Irradiation; | A 60% B 25% |
trans-1,2-cyclohexandiol
A
hexanedial
B
cyclohexane-1,2-dione
C
cyclohexanone-2-ol
Conditions | Yield |
---|---|
With oxygen; [(n-Bu)4N]3H2[IMo6O24] In acetonitrile at 80℃; under 1520.1 Torr; for 5h; | A 3% B 56% C 41% |
Conditions | Yield |
---|---|
With oxygen In acetonitrile at 25℃; for 6h; Kinetics; | A 55% B 38% |
cyclohexanone-2-ol
A
Adipic acid
B
adipic anhydride
C
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With air; chromium(III)naphthenate In chlorobenzene at 50℃; Product distribution; var. catalyst; | A 54% B 43% C 3% |
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
Stage #1: trans-cyclohexane-1,2-diol; platinum at 90℃; for 0.166667h; Stage #2: With dihydrogen peroxide In water at 90℃; for 20h; Product distribution / selectivity; | 51% |
11-hydroxytetrahydrocarbazolenine
3-chloro-benzenecarboperoxoic acid
A
o-phenol
B
cyclohexane-1,2-dione
C
3-Chloro-N-(2-hydroxy-phenyl)-N-(6-oxo-cyclohex-1-enyl)-benzamide
D
spiro[cyclopentane-1,2'-indolin]-3'-one
Conditions | Yield |
---|---|
In dichloromethane at -60℃; for 1h; | A 42% B 24% C 24% D 8% |
11-hydroxytetrahydrocarbazolenine
A
o-phenol
B
cyclohexane-1,2-dione
C
3-Chloro-N-(2-hydroxy-phenyl)-N-(6-oxo-cyclohex-1-enyl)-benzamide
D
spiro[cyclopentane-1,2'-indolin]-3'-one
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -60℃; for 1h; | A 42% B 24% C 24% D 8% |
tert-butyldimethylsilyl chloride
cyclohexane-1,2-dione
2-{(tert-butyldimethylsilyl)oxy}cyclohex-2-en-1-one
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 0.5h; | 99% |
With 1H-imidazole In dichloromethane at 23℃; for 24h; Inert atmosphere; | 98% |
With 1H-imidazole In dichloromethane at 20℃; | 95% |
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With [15N]hydroxylamine hydrochloride; potassium carbonate In water at 20℃; for 24h; | 99% |
vinyl magnesium bromide
cyclohexane-1,2-dione
2‐hydroxy‐2‐vinylcyclohexan‐1‐one
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; | 98% |
In tetrahydrofuran at 20℃; Cooling with ice; | 85% |
In tetrahydrofuran | |
In tetrahydrofuran at 0 - 20℃; Schlenk technique; Inert atmosphere; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid Reflux; | 98% |
With toluene-4-sulfonic acid In toluene for 48h; Reflux; | 69% |
With toluene-4-sulfonic acid In toluene for 48h; Reflux; | 66% |
4-fluoro-β-nitrostyrene
cyclohexane-1,2-dione
(1S,5S,6R,7S)-6-(4-fluorophenyl)-1-hydroxy-7-nitrobicyclo[3.2.1]octan-8-one
Conditions | Yield |
---|---|
With nickel diacetate; triethylamine; (1R,2R)-N,N'-di(4'-bromobenzyl)-1,2-diaminocyclohexane In tetrahydrofuran at 20℃; Michael-Henry reaction; optical yield given as %ee; enantioselective reaction; | 98% |
cyclohexane-1,2-dione
ortho-cresidine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 130℃; for 4.5h; Sealed tube; Molecular sieve; Microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With sodium chloride; zinc In methanol; water Heating; | 97% |
With ammonium chloride; zinc In tetrahydrofuran at 20℃; for 0.75h; | 92% |
With trimethylphosphane In tetrahydrofuran at 20℃; for 2h; | 80% |
cyclohexane-1,2-dione
1-triphenylphosphoranylidene-2-propanone
2-(2-oxopropyl)cyclohex-2-enone
Conditions | Yield |
---|---|
In dichloromethane for 25h; Wittig-Horner reaction; Heating; | 97% |
at 130 - 140℃; |
Conditions | Yield |
---|---|
With ozone In tetrachloromethane; water at 20℃; for 1h; UV-irradiation; | 97% |
With water; ozone at 25℃; under 760.051 Torr; for 1h; Irradiation; | 95% |
With oxygen; sodium hydroxide In water at 90℃; under 3000.3 Torr; for 3h; pH=7; | 21% |
4-bromophenylhydrazine hydrochloride
cyclohexane-1,2-dione
(E)-2-(2-(4-bromophenyl)hydrazono)cyclohexan-1-one
Conditions | Yield |
---|---|
In water at 20℃; for 16h; | 97% |
Conditions | Yield |
---|---|
With sulfuric acid In ethanol at 65℃; for 4.08333h; | 96.3% |
N-methoxylamine hydrochloride
cyclohexane-1,2-dione
cyclohexane-1,2-dione-bis-O-methyldioxime
Conditions | Yield |
---|---|
With pyridine In methanol | 96% |
Conditions | Yield |
---|---|
With indium(III) chloride; 1-butyl-3-methylimidazolium Tetrafluoroborate at 100℃; for 2h; | 96% |
With sulfuric acid; silica gel In methanol for 2h; Friedlaender Quinoline Synthesis; Reflux; | 93% |
With eaton’s reagent In neat (no solvent) at 90℃; for 3h; | 86% |
Conditions | Yield |
---|---|
In water; toluene | 95.34% |
In toluene for 5h; Inert atmosphere; Dean-Stark trap; Reflux; | 95.34% |
In toluene for 5h; Inert atmosphere; Reflux; | 95.34% |
bis(trimethylsilyl)sulphate
cyclohexane-1,2-dione
1,2-bis(trimethylsilyloxy)cyclohex-1-ene
Conditions | Yield |
---|---|
With calcium In toluene at 100℃; for 2h; Solvent; Reagent/catalyst; | 95.18% |
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With calcium In toluene at 125℃; for 2h; Solvent; Reagent/catalyst; | 95.1% |
Conditions | Yield |
---|---|
In dichloromethane for 1h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1h; | 95% |
N-(2-methyl-1-oximino-1-phenyl-2-propyl)hydroxylamine
cyclohexane-1,2-dione
5,5-dimethyl-1-hydroxy-2-(spirocyclohexan-2-one 2)-4-phenyl-3-imidazoline 3-oxide
Conditions | Yield |
---|---|
In methanol for 6h; Heating; | 95% |
Conditions | Yield |
---|---|
With acetic acid In ethanol; acetonitrile at 0 - 5℃; for 2h; Condensation; | 95% |
In ethanol at 0℃; for 3h; | 80% |
cyclohexane-1,2-dione
Conditions | Yield |
---|---|
With borate buffer at 37℃; for 18h; pH=9.0; | 95% |
4-methoxy-aniline
cyclohexane-1,2-dione
2-[(4-methoxyphenyl)amino]cyclohex-2-en-1-one
Conditions | Yield |
---|---|
In toluene for 12h; Inert atmosphere; Reflux; | 95% |
With toluene-4-sulfonic acid In toluene at 130℃; for 4.5h; Sealed tube; Molecular sieve; Microwave irradiation; | 72% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 48h; Solvent; Concentration; regioselective reaction; | 95% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 130℃; for 4.5h; Sealed tube; Molecular sieve; Microwave irradiation; | 95% |
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; silica gel at 50℃; for 3h; Temperature; Green chemistry; | 94% |
With hydroxylamine hydrochloride; potassium hydroxide In ethanol; water at 0 - 20℃; for 48h; | 87% |
With hydroxylamine | |
With potassium hydroxide; hydroxylamine hydrochloride |
cyclohexane-1,2-dione
acetylenedicarboxylic acid diethyl ester
malononitrile
ethyl 2-amino-3-cyano-4-(2-ethoxy-2-oxoethyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-4-carboxylate
Conditions | Yield |
---|---|
With copper(II) ferrite In water at 60℃; for 2h; | 94% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 130℃; for 4.5h; Sealed tube; Molecular sieve; Microwave irradiation; | 94% |
Chemical Name: 1,2-Cyclohexanedione
IUPAC NAME: Cyclohexane-1,2-dione
CAS No.: 765-87-7
EINECS: 212-155-3
RTECS: GV0340000
Molecular Formula: C6H8O2
Molecular Weight: 112.13 g/mol
Melting Point: 35 °C
Density: 1.127 g/cm3
Flash Point: 66.9 °C
Boiling Point: 194 °C at 760 mmHg
Storage temp.: 0-6°C
Following is the structure of 1,2-Cyclohexanedione (765-87-7):
Product Categories about 1,2-Cyclohexanedione (765-87-7) are Ketone ; Pharmaceutical intermediate ; C3 to C6Protein Modification ; Reagents for arginine modification ; Carbonyl Compounds ; Ketones ; Specific Amino Acid Modification
The chemical synonymous of 1,2-Cyclohexanedione (765-87-7) are 1,2-Cyclohexadione ; 1,2-Dioxocyclohexane ; Cyclohexane-1,2-dione ; Dihydrocatechol ; 1,2-Cyclohexandione ; 1,2-Cyclohexanedione ; 2-Hydroxy-2-cyclohexen-1-one ; 2-Hydroxy-cyclohex-2-enone
1,2-Cyclohexanedione (765-87-7) is mainly used in organic synthesis.
1. | unr-mus LD50:440 mg/kg | PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. 12 (1978),227. |
Reported in EPA TSCA Inventory.
Moderately toxic by unspecified route. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Note: Irritant
Hazard Codes:
Xn: Harmful
Xi: Irritant
Risk Statements about 1,2-Cyclohexanedione (765-87-7):
R22 Harmful if swallowed.
Safety Statements about 1,2-Cyclohexanedione (765-87-7):
S24/25: Avoid contact with skin and eyes.
Attentions:
1. Storage: Keep away from sources of ignition. Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4°C/39°F.) Store under an inert atmosphere.
2. Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
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