Product Name

  • Name

    Cyclohexanone

  • EINECS 203-631-1
  • CAS No. 108-94-1
  • Article Data2587
  • CAS DataBase
  • Density 0.947 g/cm3
  • Solubility Water solubility: 150 g/L (10 °C)
  • Melting Point -16.4 °C
  • Formula C6H10O
  • Boiling Point 155.65 °C
  • Molecular Weight 98.1448
  • Flash Point 44 °C
  • Transport Information UN 1915 3/PG 3
  • Appearance colourless liquid
  • Safety 25
  • Risk Codes 10-20
  • Molecular Structure Molecular Structure of 108-94-1 (Cyclohexanone)
  • Hazard Symbols HarmfulXn
  • Synonyms AI3-00041;Anon;Anone;CCRIS 5897;Cicloesanone;Cicloesanone [Italian];Cyclohexanon;Cyclohexyl ketone;Cykloheksanon;Cykloheksanon [Polish];Hexanon;
  • PSA 17.07000
  • LogP 1.51960

Synthetic route

cyclohexenone
930-68-7

cyclohexenone

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; diisobutylaluminium hydride In tetrahydrofuran; diethyl ether; hexane at -50℃; for 0.5h;100%
With hydrogen; mer-Os(PPh3)3HBr(CO) In toluene at 100℃; under 760 Torr; for 24h;100%
With diphenylsilane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In chloroform for 1h; Ambient temperature;100%
cyclohexane
110-82-7

cyclohexane

A

cyclohexanone
108-94-1

cyclohexanone

B

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
With Fe2(4,4″-dioxido-[1,1′:4′,1″-terphenyl]-3,3″-dicarboxylate); 1-(tert-butylsulfonyl)-2-iodosylbenzene In [D3]acetonitrile at 20℃; for 1.5h;A 100%
B 100%
With 3-chloro-benzenecarboperoxoic acid; [Ni2(L2H2)(OAc)2] at 20℃; for 1h;A 7%
B 93%
With 3-chloro-benzenecarboperoxoic acid; (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride In dichloromethane; acetonitrile for 1h; Product distribution; Ambient temperature; other catalysts; kinetic isotope effect;A 2%
B 89%
cyclohexanol
108-93-0

cyclohexanol

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With sodium bromite In acetic acid for 5h; Ambient temperature;100%
With potassium permanganate; Sucrose-ethyleneoxide adducts In toluene at 20℃; for 24h; Product distribution; further catalysts: PEG, DB18K6; further objects of study: phase-transfer catalysis;;100%
With 4 A molecular sieve; tetrabutylammonium periodite; sodium ruthenate(VI) In dichloromethane at 20℃; for 24h; Oxidation;100%
cyclohexenone
930-68-7

cyclohexenone

A

cyclohexanone
108-94-1

cyclohexanone

B

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
With Geotrichum candidum CCT 1205 whole cells In aq. phosphate buffer at 28℃; for 24h; pH=6.5; Enzymatic reaction;A 100%
B n/a
With hydrogen; In methanol at 30℃; under 735.5 Torr; for 5h;A 0.8%
B 98.2%
With C8H13O2S2(3-)*Na(1+)*Rh(1+)*H(1+); hydrogen In water; toluene at 60℃; under 15001.5 Torr; for 4h; Inert atmosphere; Schlenk technique; Autoclave;A 90%
B 9%
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 3h; Heating;100%
With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 In acetonitrile for 0.333333h; Oxidation; Heating;100%
With Co1.4Cu1.6[Co(CN)6]2; oxygen In ethanol; water at 100℃; under 3750.38 Torr; for 3h; Reagent/catalyst; Time; Solvent;100%
cyclohexanone hydrazone
6156-08-7

cyclohexanone hydrazone

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With copper(II) sulfate In tetrahydrofuran; methanol; water for 2h; Heating;100%
2-methyl-1,5-dioxaspiro<5.5>undecane
6413-26-9, 147441-58-5, 147441-59-6

2-methyl-1,5-dioxaspiro<5.5>undecane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With 4-phenyl-2,2,5,5-tetramethyl-3-imidazolin-1-yloxy-3-oxide; 15-crown-5; KCrO5Cl In acetonitrile at 60℃; for 7h; Product distribution; Further Variations:; Reagents;100%
diethyl ether
60-29-7

diethyl ether

C20H30O6

C20H30O6

A

(1S,3aR,5S,5'S,6R,6a'R)-2,2'-dimethyl-5'-(2-methyl-1,3-dioxolan-4-yl)dihydro-3a'H-3-oxaspiro[bicyclo[3.2.0.]heptane-6,6'-furo[2,3-d][1,3]dioxole]
1244773-04-3

(1S,3aR,5S,5'S,6R,6a'R)-2,2'-dimethyl-5'-(2-methyl-1,3-dioxolan-4-yl)dihydro-3a'H-3-oxaspiro[bicyclo[3.2.0.]heptane-6,6'-furo[2,3-d][1,3]dioxole]

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate); benzene Inert atmosphere; Irradiation;A 65%
B 100%
...Expand
cyclohexenone
930-68-7

cyclohexenone

A

hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

B

cyclohexanone
108-94-1

cyclohexanone

C

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
With Geotrichum candidum CCT 1205 whole cells In aq. phosphate buffer at 28℃; for 24h; pH=6.5; Baeyer-Villiger Ketone Oxidation; Enzymatic reaction;A n/a
B 100%
C n/a
...Expand
14,15-dioxa-7-aza-dispiro[5.1.5.2]pentadecane
21842-28-4

14,15-dioxa-7-aza-dispiro[5.1.5.2]pentadecane

A

caprolactam
105-60-2

caprolactam

B

11-cyanoundecanoic acid
5810-18-4

11-cyanoundecanoic acid

C

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With cerium(IV) oxide; 2,2'-azobis(isobutyronitrile) at 50℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere;A n/a
B 99.2%
C n/a
...Expand
cyclohexen-1-ol
4065-81-0

cyclohexen-1-ol

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With [Ru(η(3):η(3)-C10H16)Cl(O2CCH3)] In aq. phosphate buffer at 50℃; for 10h; pH=7; Sealed tube; Inert atmosphere;99%
With perchloric acid; acetaldehyde; acetone; sodium chloride In water at 25℃; Rate constant; Equilibrium constant; Irradiation;
With sulfuric acid In water at 25℃; Rate constant; Equilibrium constant;
In water at 25℃; Equilibrium constant; ionic strength: 0.01 M;
at 19.9 - 59.9℃; Equilibrium constant; Thermodynamic data; keto-enol-tautomerism, keto-enol-association; ΔH;
cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With water at 80℃; for 0.25h; microwave irradiation;99%
With silica gel; iron(III) chloride at 20℃; for 0.0833333h;97%
With water; Nafion-H In acetone for 0.5h;95%
1,1-diethoxycyclohexane
1670-47-9

1,1-diethoxycyclohexane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With water at 80℃; for 0.25h; microwave irradiation;99%
With water; acetone; mesoporous aluminosilicate at 55℃; for 2h;85%
With aluminium(III) iodide In acetonitrile; benzene for 0.166667h; Ambient temperature;90 % Chromat.
With erbium(III) triflate In nitromethane for 0.5h; Product distribution; Further Variations:; Solvents; reaction time;
cyclohexyl-1-phenyl-1-hydroperoxide
20614-61-3

cyclohexyl-1-phenyl-1-hydroperoxide

A

cyclohexanone
108-94-1

cyclohexanone

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
Fe/W/Zr oxide catalyst of example 3 In acetone at 70℃; Product distribution / selectivity;A 99%
B 99%
With sulfuric acid In decane; nitromethane Product distribution / selectivity;A 99.56 %Chromat.
B 99.47 %Chromat.
sulfuric acid In decane; nitromethane at 53℃; Product distribution / selectivity;
2,2,3,3-tetramethyl-1,4-dioxaspiro<4.5>decane
32893-35-9

2,2,3,3-tetramethyl-1,4-dioxaspiro<4.5>decane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With iron(III) chloride hexahydrate; acetaldehyde In dichloromethane for 1h; Reflux;99%
phenol
108-95-2

phenol

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With Pd nanoparticles and TiO2; hydrogen; hydrazine hydrate In water at 80℃; under 450.045 Torr; for 10h; Catalytic behavior; Kinetics; Mechanism; Reagent/catalyst;98.9%
With hydrogen at 160 - 200℃; under 1125.11 Torr; for 1h; Reagent/catalyst; Autoclave;96.3%
With 2 mol-% Pd/C; hydrogen; potassium formate In water at 90℃; for 6h; Temperature; Reagent/catalyst;94%
cyclohexane
110-82-7

cyclohexane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With methyltrifluoromethyldioxirane In dichloromethane at -22℃; for 0.3h;98%
With hydrogenchloride; FeH6Mo6O24(3-)*3H3N*3H(1+)*7H2O; tetrabutylammomium bromide; dihydrogen peroxide In 1,4-dioxane; water at 85℃; for 24h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst;98%
With dihydrogen peroxide at 49.84℃; for 3h; Catalytic behavior; Temperature; Reagent/catalyst;93.1%
1,3-dioxolane-2-spirocyclohexane
177-10-6

1,3-dioxolane-2-spirocyclohexane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With 1,1,1-trifluoro-2-propanone; methyltrifluoromethyldioxirane In dichloromethane at 0℃; for 2h; also dimethyldioxirane efficiently afford cleavage of acetals and ketals to carbonyl products under mild, neutral conditions through α-CH insertion, also react dialkyl ethers and cyclic ethers to alcohols, aldehydes, carboxylic axids or to lactones;98%
With 1,1,1-trifluoro-2-propanone; methyltrifluoromethyldioxirane In dichloromethane at 0℃; for 2h;98%
With iron(III) chloride In dichloromethane for 0.25h; Ambient temperature;96%
1,5-dithiaspiro[5.5]undecane
180-96-1

1,5-dithiaspiro[5.5]undecane

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; dihydrogen peroxide In water; acetonitrile at 20℃; for 0.75h;98%
With acetic acid at 20℃; for 6h;82%
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 3h; Micellar solution;75%
N'-cyclohexylidene-N,N-dimethyl-hydrazine
10424-93-8

N'-cyclohexylidene-N,N-dimethyl-hydrazine

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With baker's yeast; phosphate buffer In ethanol at 37℃; for 12h;98%
With triethylene diamine nickel thiosulfate; water In chloroform at 20℃; for 0.0833333h; Hydrolysis;94%
With chloro-trimethyl-silane; sodium iodide In water; acetonitrile for 0.05h; deprotection;92%
cyclohexane-1,1-diylbis(phenylsulfane)
37457-08-2

cyclohexane-1,1-diylbis(phenylsulfane)

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20 - 25℃; for 2h; Irradiation;98%
Cyclohex-2-enol
822-67-3

Cyclohex-2-enol

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With [Ru(η(5)-C5,κ-P-Cp(P))(CH3CN)2]PF6 In tetrahydrofuran-d8 at 60℃; for 5h; Inert atmosphere;97%
With tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; potassium carbonate In acetonitrile for 1h; Inert atmosphere; Reflux;96%
With bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (1,3,5-triaza-7-phosphaadamantane); isopropyl alcohol In water at 100℃; for 1h; Reagent/catalyst;95.5%
cyclohexanone semicarbazone
1589-61-3

cyclohexanone semicarbazone

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With ammonium chlorochromate on aluminum oxide In diethyl ether for 0.5h; Heating; various conditions;97%
With zirconium hydrogen sulfate; silica gel In hexane at 20℃; for 0.3h;92%
With water; silica gel; tetrabromosilane In tetrachloromethane at 20℃; for 0.233333h;90%
3-Butyl-1,2,5-trioxa-spiro[5.5]undecan-4-one

3-Butyl-1,2,5-trioxa-spiro[5.5]undecan-4-one

A

2-oxohexanoic acid
2492-75-3

2-oxohexanoic acid

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
triethylamine In dichloromethane at 20 - 25℃; for 16h;A 97%
B n/a
cyclohexanone phenylhydrazone
946-82-7

cyclohexanone phenylhydrazone

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With baker's yeast; phosphate buffer In ethanol at 37℃; for 11h;97%
With caro's acid; silica gel for 0.05h; Oxidation; Irradiation;94%
With iron(II) sulfate In chloroform at 20℃; for 0.75h; Hydrolysis;90%
2-hexyl-1,4-dioxa-spiro[4.5]decane

2-hexyl-1,4-dioxa-spiro[4.5]decane

A

1,2-octandiol
1117-86-8

1,2-octandiol

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With sodium bromate; ammonium cerium(IV) nitrate In acetonitrile at 80℃; for 0.333333h;A 97%
B 95%
rac-octan-2-ol
4128-31-8

rac-octan-2-ol

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With C53H46ClN3P2Ru; potassium tert-butylate; acetone at 56℃; under 750.075 Torr; for 0.666667h; Oppenauer Oxidation;97%
Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

acetaldehyde
75-07-0

acetaldehyde

A

Acetaldehyde oxime
107-29-9

Acetaldehyde oxime

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With sulfuric acid at 4 - 10℃; for 2h;A 97%
B 97%
...Expand
pyrrolidine
123-75-1

pyrrolidine

cyclohexanone
108-94-1

cyclohexanone

1-(1-Cyclohexen-1-yl)pyrrolidine
1125-99-1

1-(1-Cyclohexen-1-yl)pyrrolidine

Conditions
ConditionsYield
In toluene for 18h; Molecular sieve; Dean-Stark trap; Heating / reflux;100%
With sulfuric acid In toluene Dean-Stark; Reflux;99%
With K-10 Montmorillonite clay In toluene for 2.5h; Heating;95%
furfural
98-01-1

furfural

cyclohexanone
108-94-1

cyclohexanone

(2E,6E)-2,6-bis(2-furylmethylene)cyclohexanone
62085-75-0

(2E,6E)-2,6-bis(2-furylmethylene)cyclohexanone

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 0.025h; microwave irradiation;100%
With sodium hydroxide In ethanol; water at 20℃; for 24h; Inert atmosphere; Green chemistry;99%
aluminum oxide for 0.0416667h; microwave irradiation;98%
methanol
67-56-1

methanol

cyclohexanone
108-94-1

cyclohexanone

cycloxexanone dimethyl ketal
933-40-4

cycloxexanone dimethyl ketal

Conditions
ConditionsYield
With trimethyl orthoformate at 40℃; under 6000480 Torr; for 8h;100%
With chloranil In acetonitrile for 0.5h; Irradiation;99%
With trimethyl orthoformate at 20℃; for 0.5h;98%
diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

cyclohexanone
108-94-1

cyclohexanone

ethyl cyclohexylideneacetate
1552-92-7

ethyl cyclohexylideneacetate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil for 1h;
Stage #2: cyclohexanone In tetrahydrofuran; mineral oil for 18h;		100%
With sodium hydride In tetrahydrofuran for 8h;98%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With 15-crown-5; sodium hydride In tetrahydrofuran; mineral oil at 0℃;
Stage #2: cyclohexanone In tetrahydrofuran; mineral oil at -40 - 20℃;		97%
Pentaerythritol
115-77-5

Pentaerythritol

cyclohexanone
108-94-1

cyclohexanone

7,11,18,21-tetraoxa-trispiro[5.2.2.5.2.2]heneicosane
183-10-8

7,11,18,21-tetraoxa-trispiro[5.2.2.5.2.2]heneicosane

Conditions
ConditionsYield
With sulfuric acid at 80℃;100%
With pyrographite In toluene for 8h; Heating;94%
peroxodisulfate ion; zirconium(IV) oxide In toluene for 4h; Heating;94%
1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

cyclohexanone
108-94-1

cyclohexanone

2-methyl-1,5-dioxaspiro<5.5>undecane
6413-26-9, 147441-58-5, 147441-59-6

2-methyl-1,5-dioxaspiro<5.5>undecane

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In benzene for 8.5h; Heating;100%
With pyridine; toluene-4-sulfonic acid In benzene Condensation; Heating;100%
With toluene-4-sulfonic acid In benzene Heating;81%
With MOR zeolite supported Bronsted acidic ionic liquid at 50℃; for 2h;68.1%
With toluene-4-sulfonic acid; benzene
cyclohexanone
108-94-1

cyclohexanone

cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

cyclopenta-2,4-dien-1-ylidenecyclohexane
3141-04-6

cyclopenta-2,4-dien-1-ylidenecyclohexane

Conditions
ConditionsYield
Stage #1: cyclohexanone; cyclopenta-1,3-diene With pyrrolidine In methanol at 20℃; Inert atmosphere;
Stage #2: With acetic acid In methanol for 0.15h;		100%
In methanol for 0.416667h; Ambient temperature; new method;96%
With pyrrolidine In methanol for 0.416667h; Ambient temperature;96%
cyclohexanone
108-94-1

cyclohexanone

benzaldehyde
100-52-7

benzaldehyde

2-Benzylidenecyclohexanone
5682-83-7

2-Benzylidenecyclohexanone

Conditions
ConditionsYield
Stage #1: cyclohexanone With sodium hydroxide In ethanol; water at 0 - 5℃;
Stage #2: benzaldehyde In ethanol; water		100%
With CaO modified with benzyl bromide In methanol at 65℃; under 760.051 Torr; for 3h; Reagent/catalyst; Concentration; Temperature; Time;95.8%
With N,N-Dimethyltrimethylsilylamine; magnesium bromide ethyl etherate at 20℃; for 16h; Inert atmosphere; neat (no solvent);93%
cyclohexanone
108-94-1

cyclohexanone

1-Ethynyl-1-cyclohexanol
78-27-3

1-Ethynyl-1-cyclohexanol

1,2-di(1-hydroxycyclohexyl)acetylene
78-54-6

1,2-di(1-hydroxycyclohexyl)acetylene

Conditions
ConditionsYield
Stage #1: 1-Ethynylcyclohexan-1-ol With ethylmagnesium bromide In tetrahydrofuran at 23 - 80℃;
Stage #2: cyclohexanone In tetrahydrofuran at 23 - 25℃;
Stage #3: With ammonium chloride In tetrahydrofuran; water		100%
With sodium hydroxide; tetrabutylammomium bromide In toluene at 70℃; for 2h;89%
Stage #1: 1-Ethynylcyclohexan-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: cyclohexanone With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; hexane at -78 - 20℃; for 14h;		74%
cyclohexanone
108-94-1

cyclohexanone

ethylene glycol
107-21-1

ethylene glycol

1,3-dioxolane-2-spirocyclohexane
177-10-6

1,3-dioxolane-2-spirocyclohexane

Conditions
ConditionsYield
With zeolite HSZ-360 In toluene for 3h; Heating;100%
With [Al(H2O)6][MS]3 In cyclohexane for 0.833333h; Reagent/catalyst; Dean-Stark; Reflux;100%
With AgOTf and (3-(3,5-bis(diphenylphosphino)phenyl)-pyridine) In toluene for 12h; Reflux;99%
cyclohexanone
108-94-1

cyclohexanone

ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

1,4-dithiaspiro[4.5]decane
177-16-2

1,4-dithiaspiro[4.5]decane

Conditions
ConditionsYield
With thionyl chloride; silica gel In toluene for 24h; Heating;100%
With bentonite In toluene for 3h; Heating;99%
With silica gel; iron(III) chloride In dichloromethane Ambient temperature;99%
cyclohexanone
108-94-1

cyclohexanone

allyl bromide
106-95-6

allyl bromide

1-allyl-1-cyclohexanol
1123-34-8

1-allyl-1-cyclohexanol

Conditions
ConditionsYield
With ammonium acetate; zinc In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;100%
zinc In N,N-dimethyl-formamide for 2h; Product distribution; Ambient temperature; other solvents : N,N-dimethylacetoamide, N-methyl-2-pyrrolidone, 2-pyrrolidone, 2-methyloxazoline;99%
With zinc In N,N-dimethyl-formamide for 2h; Ambient temperature; other solvents : N,N-dimethylacetoamide, N-methyl-2-pyrrolidone, 2-pyrrolidone, 2-methyloxazoline;99%
cyclohexanone
108-94-1

cyclohexanone

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

1-hydroxy-1-cyclohexanecarbonitrile
931-97-5

1-hydroxy-1-cyclohexanecarbonitrile

Conditions
ConditionsYield
With Hevea brasiliensis (S)-hydroxynitrile lyase pH=4.5; aq. buffer; Enzymatic reaction;100%
With titanium(IV) isopropylate; dl-3-(2-hydroxy-1-naphthylidene)-imino-ε-caprolactam (Nap-ACL) In dichloromethane for 3h; Ambient temperature;99%
With ytterbium(III) isopropoxide In tetrahydrofuran for 0.5h; Ambient temperature;94%
cyclohexanone
108-94-1

cyclohexanone

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-cyano-2-cyclohexylideneacetate
6802-76-2

ethyl 2-cyano-2-cyclohexylideneacetate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In neat liquid at 20℃; for 0.133333h; Knoevenagel Condensation; Green chemistry;100%
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.333333h; Knoevenagel condensation;98%
With ammonium acetate; acetic acid In toluene Knoevenagel Condensation; Reflux;97%
cyclohexanone
108-94-1

cyclohexanone

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

3H-spiro{benzothiazole-2,1'-cyclohexane}
182-53-6

3H-spiro{benzothiazole-2,1'-cyclohexane}

Conditions
ConditionsYield
With trifluoroacetic acid at 80℃; for 16h; Reagent/catalyst;100%
In toluene Heating;93.8%
With aluminum oxide In neat (no solvent) at 20℃; for 0.5h; Inert atmosphere;92%
cyclohexanone
108-94-1

cyclohexanone

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide
4545-18-0

N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide

Conditions
ConditionsYield
In methanol at 20℃; for 3h;100%
In methanol at 20℃; Inert atmosphere;99.5%
With hydrogenchloride In methanol for 24h; Heating;97%
cyclohexanone
108-94-1

cyclohexanone

benzylamine
100-46-9

benzylamine

N-benzylcyclohexylamine
4383-25-9

N-benzylcyclohexylamine

Conditions
ConditionsYield
With formic acid; Cp*IrCl(N-(phenyl(pyridin-2-yl)methyl)methanesulfonamide)complex In ethyl acetate at 40℃; for 18h; Reagent/catalyst; Inert atmosphere;100%
Stage #1: cyclohexanone; benzylamine With formic acid; chlorido(8-quinolinolato-k2N,O)(η5-pentamethylcyclopentadienyl)iridium(III) In ethyl acetate at 0 - 40℃; Inert atmosphere; Schlenk tube; Cooling with ice;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Product distribution / selectivity;		98%
With 4 A molecular sieve; borane pyridine complex In methanol for 16h;96%
cyclohexanone
108-94-1

cyclohexanone

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

1-oxa-4-thia-spiro[4.5]decane
177-15-1

1-oxa-4-thia-spiro[4.5]decane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether for 3h; Heating;100%
With hydrogenchloride In diethyl ether at 20℃; for 0.15h;98%
bis(acetylacetonato)dioxidomolybdenum(VI) In acetonitrile at 20℃; for 3.5h;96%
cyclohexanone
108-94-1

cyclohexanone

malononitrile
109-77-3

malononitrile

2-(cyclohexylidene)malononitrile
4354-73-8

2-(cyclohexylidene)malononitrile

Conditions
ConditionsYield
hydrotalcite structure integrating fluoride ions In DMF (N,N-dimethyl-formamide) at 25℃; for 2h; Conversion of starting material; Knoevenagel Condensation;100%
With 1-butyl-1,4-diazabicyclo[2.2.2]octanylium hydrotetrafluoroborate In water at 20℃; for 0.0333333h; Knoevenagel condensation;100%
Ru(+)Cp*(NCCHCO2Et)(-)*(PPh3)2 In tetrahydrofuran at 25℃; for 5h; Condensation; Aldol reaction;99%
cyclohexanone
108-94-1

cyclohexanone

hexahydro-2H-oxepin-2-one
502-44-3

hexahydro-2H-oxepin-2-one

Conditions
ConditionsYield
With Fe(AAEMA)3; oxygen; isobutyraldehyde In 1,2-dichloro-ethane under 760 Torr; for 36h; Ambient temperature;100%
With borax; dihydrogen peroxide; N-benzyl-N,N,N-triethylammonium chloride In water; benzene at 55℃; for 24h;100%
With bismuth(lll) trifluoromethanesulfonate In dichloromethane at 20℃; for 0.5h; Baeyer-Villiger oxidation;100%
cyclohexanone
108-94-1

cyclohexanone

2-bromocyclohexanone
1056477-06-5

2-bromocyclohexanone

Conditions
ConditionsYield
With N-Bromosuccinimide; toluene-4-sulfonic acid In dichloromethane; cyclohexanone at 0℃; for 4h; Reflux;100%
With N-Bromosuccinimide; toluene-4-sulfonic acid In dichloromethane at 0℃; for 4h; Reflux;98%
With Cl(CF2)4SO2Br In tetrachloromethane at 10℃; for 0.166667h;95%
cyclohexanone
108-94-1

cyclohexanone

Adipic acid
124-04-9

Adipic acid

Conditions
ConditionsYield
With sodium nitrite In trifluoroacetic acid100%
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 5.25h; Product distribution / selectivity;100%
With dihydrogen peroxide; ortho-tungstic acid In water at 90℃; for 20h; Product distribution / selectivity;99%
cyclohexanone
108-94-1

cyclohexanone

6-Hydroxyhexanoic acid
1191-25-9

6-Hydroxyhexanoic acid

Conditions
ConditionsYield
Stage #1: cyclohexanone With potassium peroxomonosulfate In water at 20℃; Baeyer-Villiger oxidation;
Stage #2: With water at 20℃; Solvolysis; Further stages.;		100%
With dihydrogen peroxide; n-butylstannoic acid; acetic acid at 70℃; for 8h;87%
With Oxone In hexane; water at 40℃; for 6h; Baeyer-Villiger oxidation;77%
cyclohexanone
108-94-1

cyclohexanone

Cyclohexanone oxime
100-64-1

Cyclohexanone oxime

Conditions
ConditionsYield
With N,O-bis(trimethylsilyl)hydroxylamine; potassium hydride In tetrahydrofuran for 1.5h; Ambient temperature; - 78 deg C to room temp.;100%
With acetic acid; acetone oxime at 120℃; for 1h;100%
With ammonium chloride; Amberlyst A-21 In ethanol for 1h; Ambient temperature;100%
cyclohexanone
108-94-1

cyclohexanone

2-Chlorocyclohexanone
822-87-7

2-Chlorocyclohexanone

Conditions
ConditionsYield
With iodine; mercury dichloride In dichloromethane for 0.5h; Ambient temperature;100%
With N-chloro-succinimide In dimethyl sulfoxide at 20℃; for 0.166667h;92%
With N-chloro-succinimide In various solvent(s) at 20℃; for 0.416667h;90%
cyclohexanone
108-94-1

cyclohexanone

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
With hydrogen; 5 percent Rh/MgO; magnesium oxide In water at 323℃; under 15001.2 Torr; Product distribution;100%
With Triethoxysilane; benzoic acid ethyl ester; cesium fluoride at 25℃; for 0.0166667h;100%
With zinc(II) tetrahydroborate In acetonitrile for 0.166667h; Ambient temperature;100%
ethanol
64-17-5

ethanol

cyclohexanone
108-94-1

cyclohexanone

1,1-diethoxycyclohexane
1670-47-9

1,1-diethoxycyclohexane

Conditions
ConditionsYield
With trimethyl orthoformate at 60℃; under 6000480 Torr; for 8h;100%
With orthoformic acid triethyl ester at 20℃; for 1h;96%
iodine for 1h;90%

Cyclohexanone Consensus Reports

Reported in EPA TSCA Inventory.

Cyclohexanone Standards and Recommendations

OSHA PEL: TWA 25 ppm (skin)
ACGIH TLV: TWA 20 ppm, STEL 50 ppm (skin); Confirmed Animal Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
NIOSH REL: (Ketone (Cyclohexanone)) TWA 100 mg/m3
DOT Classification:  3; Label: Flammable Liquid

Cyclohexanone Analytical Methods

For occupational chemical analysis use OSHA: #01 or NIOSH: Ketones I (Desorption in CS2), 1300.

Cyclohexanone Specification

Cyclohexanone, with the CAS register number 108-94-1, is a colorless to pale yellow liquid with a pleasant odor. It is the organic compound with the formula C6H10O. Its EINECS register number is 203-631-1. Cyclohexanone is slightly soluble in water (5-10 g/100 mL), but miscible with ethanol. The substance is stable and combustible, which is incompatible with strong oxidizing agents.Cyclohexanone can form an explosive peroxide with H2O2 and react vigorously with oxidizing materials, such as nitric acid. It is easily ignited by heat, sparks or flames. It will form vapors when it is mixed with air. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas. Its container may explode when heated.

Physical properties about Cyclohexanone are: (1)ACD/LogP: 0.821; (2)ACD/LogD (pH 5.5): 0.82; (3)ACD/LogD (pH 7.4): 0.82; (4)ACD/BCF (pH 5.5): 2.48; (5)ACD/BCF (pH 7.4): 2.48; (6)ACD/KOC (pH 5.5): 66.58; (7)ACD/KOC (pH 7.4): 66.58; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.453; (10)Molar Refractivity: 27.801 cm3; (11)Molar Volume: 102.952 cm3; (12)Polarizability: 11.021 10-24cm3; (13)Surface Tension: 32.523998260498 dyne/cm; (14)Density: 0.953 g/cm3; (15)Flash Point: 46.667 °C; (16)Enthalpy of Vaporization: 39.248 kJ/mol; (17)Boiling Point: 155.749 °C at 760 mmHg; (18)Vapour Pressure: 2.98600006103516 mmHg at 25°C

Preparation of Cyclohexanone: Cyclohexanone can be prepared from cyclohexanol by oxidation with chromic oxide. In addition, it can be produced by the partial hydrogenation of phenol:

C6H5OH + 2 H2 → (CH2)5CO

Besides, Cyclohexanone is also produced by the oxidation of cyclohexane in air, typically using cobalt catalysts:

C6H12 + O2 → (CH2)5CO + H2O

Uses of Cyclohexanone: The great majority of Cyclohexanone is used as the precursors in production of adipic acid, caprolactam, Nylon 6,6 and Nylon 6. It can be used to make nylon, as a chemical reaction medium, and as a solvent, for instance, used in paint, especially in the paint which contains nitrocellulose, polymer or copolymer of chloroethene and polymer of methylacrylic acid ester. Cyclohexanone can also be used in dyeing and as levelling agent of faded light silk.

When you are using Cyclohexanone, you should be very cautious about it. The substance is flammable and harmful, which is harmful by inhalation. What's more, you must avoid contact with your eyes.

You can still convert the following datas into molecular structure of Cyclohexanone:
(1)Canonical SMILES: C1CCC(=O)CC1
(2)InChI: InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
(3)InChIKey: JHIVVAPYMSGYDF-UHFFFAOYSA-N

Toxicity of Cyclohexanone:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo subcutaneous 1900mg/kg (1900mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 50, Pg. 199, 1903.
guinea pig LCLo inhalation 400ppm/4H (400ppm)   National Technical Information Service. Vol. AD-A066-307,
guinea pig LDLo intraperitoneal 760mg/kg (760mg/kg)   National Technical Information Service. Vol. AD-A066-307,
human TCLo inhalation 75ppm (75ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 282, 1943.
mammal (species unspecified) LC50 inhalation 25gm/m3 (25000mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
mammal (species unspecified) LD50 oral 3gm/kg (3000mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
monkey LDLo intravenous 284mg/kg (284mg/kg)   Toxicology and Applied Pharmacology. Vol. 37, Pg. 115, 1976.
mouse LCLo inhalation 19200mg/m3/90 (19200mg/m3) GASTROINTESTINAL: OTHER CHANGES Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979.
mouse LD50 intraperitoneal 1230mg/kg (1230mg/kg) GASTROINTESTINAL: OTHER CHANGES Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979.
mouse LD50 oral 1400mg/kg (1400mg/kg)   National Technical Information Service. Vol. AD-A066-307,
mouse LDLo subcutaneous 1300mg/kg (1300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ATAXIA		 Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 50, Pg. 199, 1903.
rabbit LD50 intraperitoneal 1540mg/kg (1540mg/kg) GASTROINTESTINAL: OTHER CHANGES Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979.
rabbit LD50 skin 1mL/kg (1mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rabbit LDLo oral 1600mg/kg (1600mg/kg) BEHAVIORAL: GENERAL ANESTHETIC Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 199, 1943.
rat LC50 inhalation 8000ppm/4H (8000ppm)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 18, 1974.
rat LD50 intraperitoneal 1130mg/kg (1130mg/kg) GASTROINTESTINAL: OTHER CHANGES Toxicology and Applied Pharmacology. Vol. 49, Pg. 525, 1979.
rat LD50 oral 1620uL/kg (1.62mL/kg)   American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rat LD50 subcutaneous 2170mg/kg (2170mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 415, 1943.
rat LDLo intravenous 568mg/kg (568mg/kg)   Toxicology and Applied Pharmacology. Vol. 37, Pg. 115, 1976.

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