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589-92-4

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589-92-4 Usage

Description

4-methylcyclohexanone is a colorless liquid with a musty animalistic odor. It is used as a food additive.

Chemical Properties

Different sources of media describe the Chemical Properties of 589-92-4 differently. You can refer to the following data:
1. CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID
2. 4-Methylcyclohexanone has an acetone-like odor.

Uses

Different sources of media describe the Uses of 589-92-4 differently. You can refer to the following data:
1. Intermediates of Liquid Crystals
2. 4-Methylcyclohexanone was used in the synthesis of the pinguisane-type sesquiterpenoid acutifolone A, in racemic form. It is used as intermediates of CCNU and it can be also be used as a solvent.

Preparation

By oxidation of a mixture of cis- and trans-4-methylcyclohexanol.

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 2011, 1973 DOI: 10.1021/jo00951a009Tetrahedron Letters, 25, p. 173, 1984 DOI: 10.1016/S0040-4039(00)99832-0

General Description

4-Methylcyclohexanone is a cyclic flavor ketone that is reported to be present in volatile oil of roasted sesame seeds.

Flammability and Explosibility

Flammable

Purification Methods

Dry the ketone with CaSO4, then fractionally distil it. The semicarbazone has m 197o , 203.5o(dec) (from MeOH or EtOH). [White & Bishop J Am Chem Soc 62 8 1945, Vogel & Oommen J Chem Soc 774 1930, Beilstein 7 III 63, 7 IV 44.]

Check Digit Verification of cas no

The CAS Registry Mumber 589-92-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 9 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 589-92:
(5*5)+(4*8)+(3*9)+(2*9)+(1*2)=104
104 % 10 = 4
So 589-92-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H12O/c1-6-2-4-7(8)5-3-6/h6H,2-5H2,1H3

589-92-4 Well-known Company Product Price

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  • Alfa Aesar

  • (A13186)  4-Methylcyclohexanone, 98+%   

  • 589-92-4

  • 25g

  • 215.0CNY

  • Detail
  • Alfa Aesar

  • (A13186)  4-Methylcyclohexanone, 98+%   

  • 589-92-4

  • 100g

  • 729.0CNY

  • Detail
  • Alfa Aesar

  • (A13186)  4-Methylcyclohexanone, 98+%   

  • 589-92-4

  • 500g

  • 3099.0CNY

  • Detail

589-92-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Methylcyclohexanone

1.2 Other means of identification

Product number -
Other names Cyclohexanone, 4-methyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Flavouring Agent: FLAVOURING_AGENT
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:589-92-4 SDS

589-92-4Synthetic route

p-methylcyclohexanol
589-91-3

p-methylcyclohexanol

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With jones reagent; silica gel In dichloromethane for 0.0833333h;98%
With aluminum oxide; sodium bromite In dichloromethane for 24h; Ambient temperature;96%
With oxygen; benzaldehyde In chloroform at 60℃; for 6h;96%
4-methylcyclohexanone oxime
4994-13-2, 128925-57-5, 128925-58-6

4-methylcyclohexanone oxime

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With bismuth(III) nitrate; silica gel In tetrahydrofuran; water for 2h; Heating;97%
p-cresol
106-44-5

p-cresol

A

trans-4-methylcyclohexan-1-ol
7731-29-5

trans-4-methylcyclohexan-1-ol

B

cis-4-methylcyclohexanol
7731-28-4

cis-4-methylcyclohexanol

C

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methyl cyclohexane at 80℃; under 1125.09 Torr; Product distribution; Rate constant; other pressures, samples of Pd/C of the various sodium content;A n/a
B n/a
C 88.4%
With hydrogen; Rh/Zr zeolite beta-supported In isopropyl alcohol at 80℃; under 3750.38 Torr; for 8h; Product distribution; Further Variations:; Catalysts; Solvents;
4-methylcyclohexanone dimethyl acetal
18349-20-7

4-methylcyclohexanone dimethyl acetal

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate; silica gel In water for 0.0166667h; microwave irradiation;88%
8-methyl-1,4-dioxaspiro[4.5]decane.
935-51-3

8-methyl-1,4-dioxaspiro[4.5]decane.

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate; silica gel In water for 0.05h; microwave irradiation;82%
With sulfuric acid In tetrahydrofuran; water
p-cresol
106-44-5

p-cresol

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With 5% palladium on Al2O3; hydrogen In 1,2-dichloro-ethane at 60℃; under 3750.38 Torr; for 24h; chemoselective reaction;81%
With hydrogen; palladium In water at 100℃; under 750.075 Torr; for 6h; Sealed;
With hydrogen In dichloromethane at 50℃; under 7500.75 Torr; for 1h;
p-4(8)-Menthene oxide
5718-78-5

p-4(8)-Menthene oxide

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With jones' reagent In acetone at 15 - 20℃; for 0.5h;80%
1,2-bis(4-methylcyclohexylidene)hydrazine
92377-01-0

1,2-bis(4-methylcyclohexylidene)hydrazine

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With HOF* CH3CN In dichloromethane at 0℃; for 0.0166667h;80%
p-methylcyclohexanol
589-91-3

p-methylcyclohexanol

A

4-methyl-2-(4-methyl-1-cyclohexenyl)cyclohexanone
13705-82-3

4-methyl-2-(4-methyl-1-cyclohexenyl)cyclohexanone

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With bromobenzene; sodium hydride; 1,2-bis-(diphenylphosphino)ethane; palladium diacetate In N,N-dimethyl-formamide at 70℃; for 3h; Product distribution; tetrakis(triphenylphosphine)palladium, K2CO3, 110 degC, 7 h;A 20%
B 73%
With bromobenzene; sodium hydride; palladium diacetate; 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 70℃; for 3h;A 20%
B 73%
trans-4-methylcyclohexan-1-ol
7731-29-5

trans-4-methylcyclohexan-1-ol

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With dimethyl sulfoxide; triethylamine; trichloromethyl chloroformate In dichloromethane71%
With potassium dichromate; sulfuric acid
With chromium(VI) oxide
4-Methylanisole
104-93-8

4-Methylanisole

A

p-cresol
106-44-5

p-cresol

C

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium In tetrahydrofuran; ethanol at -30℃; for 2h;A 41%
B 50%
C 4%
cis-1-Methoxy-4-methylcyclohexane
25904-15-8

cis-1-Methoxy-4-methylcyclohexane

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With HOF* CH3CN; sodium fluoride In chloroform; water; acetonitrile Ambient temperature;A 50%
B 40%
tert-butyldimethyl((4-methylcyclohex-1-en-1-yl)oxy)silane

tert-butyldimethyl((4-methylcyclohex-1-en-1-yl)oxy)silane

A

(S)-tert-butyldimethyl((4-methylcyclohex-1-en-1-yl)oxy)silane

(S)-tert-butyldimethyl((4-methylcyclohex-1-en-1-yl)oxy)silane

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
Stage #1: tert-butyldimethyl((4-methylcyclohex-1-en-1-yl)oxy)silane With C116H73F10N3O8P2S2 In toluene at 25℃; for 0.0833333h; Resolution of racemate;
Stage #2: With 2-Biphenylcarboxylic acid In toluene at -30℃; for 20h; Resolution of racemate;
A 42%
B 50%
p-methylcyclohexanol
589-91-3

p-methylcyclohexanol

A

trans-4-methylcyclohexan-1-ol
7731-29-5

trans-4-methylcyclohexan-1-ol

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; dimethylsulfide; oxygen; copper(I) bromide dimethylsulfide complex; 6,6'-bis(C8F17(CH2)4)-2,2'-bipyridine In chlorobenzene at 90℃; for 1.8h;A 49%
B 45%
methyl cyclohexane
82166-21-0

methyl cyclohexane

A

1-Methylcyclohexanol
590-67-0

1-Methylcyclohexanol

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

C

3-Methylcyclohexanone
591-24-2, 625-96-7

3-Methylcyclohexanone

Conditions
ConditionsYield
With [FeCl(ind)]2O; dihydrogen peroxide In acetonitrile at 25℃; for 10h;A 4.2%
B 2.8%
C 6.2%
With C12H6N2O4(2-)*Al(3+)*HO(1-)*0.5H2O; oxygen In acetonitrile at 0 - 150℃; under 7500.75 Torr; for 4h; Autoclave;
1-Nitrooxy-bicyclo[2.2.1]heptane
249904-46-9

1-Nitrooxy-bicyclo[2.2.1]heptane

A

3-ethylcyclopentanone
86505-42-2, 86505-49-9, 10264-55-8

3-ethylcyclopentanone

B

1-norbornyl alcohol
51566-98-4

1-norbornyl alcohol

C

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With azobisisobutyronitrile; tri-n-butyl-tin hydride In benzene for 48h; Ring cleavage; Heating;A n/a
B 3%
C n/a
4-methylcyclohexene
591-47-9

4-methylcyclohexene

A

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

B

3-Methylcyclohexanone
591-24-2, 625-96-7

3-Methylcyclohexanone

Conditions
ConditionsYield
With palladium(II) sulfate; oxygen; H3PMo6W6O40 In cyclohexane; water at 29.9℃; under 760 Torr; for 18h; Rate constant;A 0.8%
B 1.7%
With dinitrogen monoxide at 220℃; for 5h; pressure;
3-methyl-7-oxabicyclo[4.1.0]heptane
36099-51-1, 103189-46-4, 103189-47-5

3-methyl-7-oxabicyclo[4.1.0]heptane

(+/-)-cis-3-methyl-cyclopentane-carbaldehyde-(1)
82879-57-0

(+/-)-cis-3-methyl-cyclopentane-carbaldehyde-(1)

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With kieselguhr at 220 - 230℃;
cis-4-methylcyclohexanol
7731-28-4

cis-4-methylcyclohexanol

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid
With chromium(VI) oxide
With oxygen; acetic acid; [Pd{N,N'-di(2,6-di-iPrC6H3)dihydroimidazol-2-yl}(OAc)2(H2O)] In toluene at 60℃; for 13h;
With (1,3-diarylimidazol-2-ylidene)-based Pd; oxygen; acetic acid In toluene at 60℃; for 13h;
methoxy-1 methyl-4 cyclohexene-1
52662-20-1

methoxy-1 methyl-4 cyclohexene-1

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
Hydrolysis;
1-hydroxy-4-methyl-cyclohexanecarboxylic acid
41248-15-1

1-hydroxy-4-methyl-cyclohexanecarboxylic acid

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With sulfuric acid at -10℃;
1-hydroxy-4-methyl-cyclohexanecarboxylic acid-(4-methyl-cyclohex-1-enyl ester)
94092-43-0

1-hydroxy-4-methyl-cyclohexanecarboxylic acid-(4-methyl-cyclohex-1-enyl ester)

A

1-hydroxy-4-methyl-cyclohexanecarboxylic acid
41248-15-1

1-hydroxy-4-methyl-cyclohexanecarboxylic acid

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With potassium hydroxide substance of mp: 82 degree;
ethanol
64-17-5

ethanol

1-hydroxy-4-methyl-cyclohexanecarbonitrile
933-45-9

1-hydroxy-4-methyl-cyclohexanecarbonitrile

A

hydrogen cyanide
74-90-8

hydrogen cyanide

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
at 25℃; Equilibrium constant;
methanol
67-56-1

methanol

4-Methylanisole
104-93-8

4-Methylanisole

A

4-methoxy-4-methylcyclohexan-1-one
23438-15-5

4-methoxy-4-methylcyclohexan-1-one

B

4-methyl-3-cyclohexen-1-one
5259-65-4

4-methyl-3-cyclohexen-1-one

C

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
Yield given. Multistep reaction;
4-Methylanisole
104-93-8

4-Methylanisole

A

4-methyl-3-cyclohexen-1-one
5259-65-4

4-methyl-3-cyclohexen-1-one

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
1) Birch reduction, 2) acid hydrolysis; Multistep reaction;
p-cresol
106-44-5

p-cresol

A

4-methyl-3-cyclohexen-1-one
5259-65-4

4-methyl-3-cyclohexen-1-one

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With oxalic acid Multistep reaction;
propyl cyanide
109-74-0

propyl cyanide

p-methylcyclohexanol
589-91-3

p-methylcyclohexanol

A

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

B

N-butyl-4-methylcyclohexylamine

N-butyl-4-methylcyclohexylamine

C

N-butyl-4-methylcyclohexylamine

N-butyl-4-methylcyclohexylamine

D

trans-N,N-dibutyl-4-methylcyclohexylamine

trans-N,N-dibutyl-4-methylcyclohexylamine

E

cis-N,N-dibutyl-4-methylcyclohexylamine

cis-N,N-dibutyl-4-methylcyclohexylamine

F

4,4'-dimethyldicyclohexylamine

4,4'-dimethyldicyclohexylamine

Conditions
ConditionsYield
aluminum oxide; lithium hydroxide; copper at 220℃; under 11400 Torr; for 0.3h; Product distribution; Mechanism;
p-methylcyclohexanol
589-91-3

p-methylcyclohexanol

A

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

B

4-methyl-6-chlorohexanal

4-methyl-6-chlorohexanal

Conditions
ConditionsYield
With lead(IV) acetate; acetic acid; lithium chloride In benzene at 70 - 80℃; for 0.166667h; Yield given. Yields of byproduct given;
With lead(IV) acetate; acetic acid; lithium chloride In benzene at 70 - 80℃; for 0.166667h; Product distribution; Mechanism; percent of conversion, ratio of cis:trans isomers of alcohol after the reaction;A 35 % Turnov.
B 63 % Turnov.
n-hexan-3-one
589-38-8

n-hexan-3-one

4-Methyl-cyclohexylidene-oxonium

4-Methyl-cyclohexylidene-oxonium

A

protonated 3-hexanone
83238-66-8

protonated 3-hexanone

B

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
Equilibrium constant; Thermodynamic data; Gas phase. Determ. by ICR spect.;
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

3-methyladipic acid
3058-01-3, 81177-02-8

3-methyladipic acid

Conditions
ConditionsYield
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 5.25h; Product distribution / selectivity;100%
With water; oxygen im Licht;
With potassium permanganate; sodium carbonate
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

4-methyl-1-(trimethylsilyloxy)-1-cyclohexene
38671-78-2

4-methyl-1-(trimethylsilyloxy)-1-cyclohexene

Conditions
ConditionsYield
Stage #1: 1-methylcyclohexan-4-one With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: chloro-trimethyl-silane With triethylamine In tetrahydrofuran; hexane at -78 - 20℃; for 1h;
100%
With lithium diisopropyl amide In tetrahydrofuran 1.) -78 deg C, 1 h, 2.) room temperature, 1 h;96%
With triethylamine In benzene for 72h; Heating;92%
trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

4-methyl-1-(trimethylsilyloxy)-1-cyclohexene
38671-78-2

4-methyl-1-(trimethylsilyloxy)-1-cyclohexene

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 1.5h;100%
With triethylamine In dichloromethane for 1h;
benzaldehyde
100-52-7

benzaldehyde

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

2-benzylidene-4-methylcyclohexanone
75910-68-8, 18020-43-4

2-benzylidene-4-methylcyclohexanone

Conditions
ConditionsYield
sodium hydroxide In water at 97℃; for 4h;100%
With sodium hydroxide In water at 100℃;
With CoFe2O4 nanoparticles/lamellar mesopore silica anchored to melamine nanocomposite In ethanol at 25℃;
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

di-p-tolylamine
620-93-9

di-p-tolylamine

Conditions
ConditionsYield
99.6%
99.8%
53.7%
51.6%
With urea In diethylene glycol dimethyl ether; water at 150℃; under 760.051 Torr; for 24h; Schlenk technique; Inert atmosphere;84 %Chromat.
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
With acyltransferase from Mycobacterium smegmatis; dihydrogen peroxide; ethyl acetate In water at 35℃; for 60h; Baeyer-Villiger Ketone Oxidation; Enzymatic reaction;99%
With oxygen; benzaldehyde In 1,2-dichloro-ethane at 20℃; for 14h; Baeyer-Villiger Ketone Oxidation;99%
With N-hydroxyphthalimide; oxygen; benzaldehyde In 1,2-dichloro-ethane at 40℃; for 8h; Baeyer-Villiger Ketone Oxidation;99.7%
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

p-methylcyclohexanol
589-91-3

p-methylcyclohexanol

Conditions
ConditionsYield
With isopropyl alcohol; zirconium(IV) oxide for 2h; Rate constant; Heating;99%
With isopropyl alcohol; zirconium(IV) oxide for 2h; Heating;99%
With isopropyl alcohol; 20% of binder (alumina) and 60% of a β zeolite at 80℃; for 5 - 12h; Heating / reflux;99.5%
ethane-1,2-dithiol
540-63-6

ethane-1,2-dithiol

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

8-methyl-1,4-dithia-spiro[4.5]decane
41158-95-6

8-methyl-1,4-dithia-spiro[4.5]decane

Conditions
ConditionsYield
With silica gel; iron(III) chloride In dichloromethane Ambient temperature;99%
sulfonated charcoal In benzene Heating;93%
With silica gel; toluene-4-sulfonic acid In dichloromethane for 6h; Heating;87%
With hydrogenchloride; zinc(II) chloride
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

phenylhydrazine
100-63-0

phenylhydrazine

3-methyl-2,3,4,9-tetrahydro-1H-carbazole
6933-54-6, 100986-21-8

3-methyl-2,3,4,9-tetrahydro-1H-carbazole

Conditions
ConditionsYield
With trichloroacetic acid at 100℃; for 0.0833333h; Fischer indole synthesis;99%
With potassium hydrogensulfate; silica gel for 0.0166667h; microwave irradiation;95%
With 1,3-bis(3-sulfopropyl)-1H-imidazol-3-ium hydrogensulfate In water at 100℃; for 1h; Fischer indole synthesis;90%
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl 4-methylcyclohexylideneacetate
127180-76-1, 42778-89-2, 191113-70-9

ethyl 4-methylcyclohexylideneacetate

Conditions
ConditionsYield
In acetonitrile at 190℃; for 0.333333h; microwave heating;99%
With (-)-trans-2,3-bis(hydroxydiphenylmethyl)-1,4-dioxaspiro<4.4>nonane(1b) at 70℃; for 4h; solid state reaction;73%
In acetonitrile at 190℃; for 0.333333h; Wittig reaction; microwave irradiation;60%
With (-)-trans-4,5-bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxacyclopentane(1a) at 70℃; for 4h; Product distribution; solid state reaction;other cyclohexanone; other optically active hosts; optical. induc.;50.8%
at 160℃; for 4h;50%
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

4-methylcyclohexane-2,2,6,6-2H4
54725-39-2

4-methylcyclohexane-2,2,6,6-2H4

Conditions
ConditionsYield
With water-d2; sodium carbonate at 120℃; for 16h; Sealed tube;99%
With water-d2; base
triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

4-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene
125332-27-6

4-methyl-1-triisopropylsilyl(oxy)-cyclohex-1-ene

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃;99%
With triethylamine In dichloromethane for 0.5h;99%
2-nitrobenzamide
610-15-1

2-nitrobenzamide

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

1'-hydroxy-4-methylspiro[cyclohexane-1,2'(1'H)-quinazolin]-4'(3'H)-one
1068135-53-4

1'-hydroxy-4-methylspiro[cyclohexane-1,2'(1'H)-quinazolin]-4'(3'H)-one

Conditions
ConditionsYield
With tin(ll) chloride In ethanol; water at 20℃; for 2h;99%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

(2S,4S)-2-((1'R)-hydroxy(4-nitrophenyl)methyl)-4-methylcyclohexan-1-one

(2S,4S)-2-((1'R)-hydroxy(4-nitrophenyl)methyl)-4-methylcyclohexan-1-one

Conditions
ConditionsYield
With acetic acid; (2S)-N-phenylpyrrolidine-2-carboxamide In m-xylene at -20℃; for 24h; aldol reaction; optical yield given as %ee; enantioselective reaction;99%
With C15H21NO4; water at 20℃; for 12h; asymmetric aldol reaction; optical yield given as %ee; diastereoselective reaction;98%
Stage #1: 1-methylcyclohexan-4-one With (S)-N-cyclopropyl-pyrrolidine-2-carboxamide; acetic acid In m-xylene at 20℃; for 0.166667h;
Stage #2: 4-nitrobenzaldehdye In m-xylene at -20℃; for 24h; optical yield given as %ee; enantioselective reaction;
95%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

(2S)-2-((R)-hydroxy(4-nitrophenyl)methyl)-4-methylcyclohexan-1-one

(2S)-2-((R)-hydroxy(4-nitrophenyl)methyl)-4-methylcyclohexan-1-one

Conditions
ConditionsYield
With C35H47N4O6(1+)*F6P(1-); water at 20℃; for 24h; Aldol Addition; enantioselective reaction;99%
With O-(n-hexanoyl)-L-serine hydrochloride; triethylamine In water at 20℃; for 30h; Aldol reaction; optical yield given as %ee; enantioselective reaction;90%
With (S)-N-{(R)-1-[3-(3,5-bis(trifluoromethyl)phenyl)ureido]-2-phenylethyl}pyrrolidine-2-carboxamide; 4-nitro-benzoic acid In toluene at -20℃; for 24h; Aldol Addition; enantioselective reaction;90%
3-(diethyoxyphosphorylmethyl)benzoic acid methyl ester
96534-02-0

3-(diethyoxyphosphorylmethyl)benzoic acid methyl ester

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

methyl 3-[(4-methylcyclohexylidene)methyl]benzoate

methyl 3-[(4-methylcyclohexylidene)methyl]benzoate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;99%
5-chloro-pyridin-2-yl hydrazine
27032-63-9

5-chloro-pyridin-2-yl hydrazine

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

4-methylcyclohexanone (5-chloropyridin-2-yl)hydrazone

4-methylcyclohexanone (5-chloropyridin-2-yl)hydrazone

Conditions
ConditionsYield
In ethanol for 0.5h; Reflux;99%
5-bromo-2-hydroxybenzamide
6329-74-4

5-bromo-2-hydroxybenzamide

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

6-bromo-4'-methylspiro[1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one

6-bromo-4'-methylspiro[1,3-benzoxazine-2,1'-cyclohexan]-4(3H)-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 8h; Reflux; Dean-Stark;99%
benzaldehyde
100-52-7

benzaldehyde

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

aniline
62-53-3

aniline

C20H23NO

C20H23NO

Conditions
ConditionsYield
With core-shell Fe3O4/saponin/Cd nanoparticles In ethanol at 20℃; for 0.916667h; Mannich Aminomethylation;99%
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

p-toluidine
106-49-0

p-toluidine

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

di-p-tolylamine
620-93-9

di-p-tolylamine

Conditions
ConditionsYield
palladium-carbon In water; N,N-dimethyl-formamide; benzene98.6%
palladium-carbon In water; N,N-dimethyl-formamide; benzene98.6%
ethylene glycol
107-21-1

ethylene glycol

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

8-methyl-1,4-dioxaspiro[4.5]decane.
935-51-3

8-methyl-1,4-dioxaspiro[4.5]decane.

Conditions
ConditionsYield
sulfonated charcoal In benzene Heating;98%
With iodine at 20℃; Ionic liquid;94%
With iodine for 16h;90%
3-methoxy-1,5-dihydro-3H-2,4-benzodioxepine
67461-24-9

3-methoxy-1,5-dihydro-3H-2,4-benzodioxepine

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

C15H20O2
125426-00-8

C15H20O2

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,2-dimethoxyethane for 0.5h; Ambient temperature;98%
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

phthalyl alcohol
612-14-6

phthalyl alcohol

C15H20O2
125426-00-8

C15H20O2

Conditions
ConditionsYield
sulfonated charcoal In benzene Heating;98%
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-amino-6-methyl-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester
76981-71-0

2-amino-6-methyl-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With morpholine; sulfur In ethanol at 50℃;98%
With morpholine; aluminum oxide; sulfur for 0.166667h; microwave irradiation;87%
With morpholine; sulfur In ethanol at 85℃; for 5h;86.98%
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

4'-methyl-1,3-dihydro-2H-benzimidazole-2-spirocyclohexane
54825-21-7

4'-methyl-1,3-dihydro-2H-benzimidazole-2-spirocyclohexane

Conditions
ConditionsYield
In sulfolane for 2h; Heating;98%
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

(2R,4S)-4-azido-2-hydroxypentane
167957-72-4

(2R,4S)-4-azido-2-hydroxypentane

(1'S,3'R,5S)-5-methyl-1-(3'-hydroxy-1'-methylbutyl)-hexahydro-2H-azepin-2-one

(1'S,3'R,5S)-5-methyl-1-(3'-hydroxy-1'-methylbutyl)-hexahydro-2H-azepin-2-one

Conditions
ConditionsYield
Stage #1: 1-methylcyclohexan-4-one; (2S,4R)-2-azido-4-hydroxypentane With boron trifluoride diethyl etherate
Stage #2: With potassium hydroxide
98%
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

4-methylcyclohexane-1,1-diyl dihydroperoxide
27470-41-3

4-methylcyclohexane-1,1-diyl dihydroperoxide

Conditions
ConditionsYield
With dihydrogen peroxide; iodine In acetonitrile at 20℃; for 5h;98%
With dihydrogen peroxide; iodine In acetonitrile at 22℃; for 5h;98%
With oxygen; 9,10-phenanthrenequinone; isopropyl alcohol for 10h; visible light irradiation;97%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

4-methyl-1-(trimethylsiloxy)cyclohexanecarbonitrile
1024020-49-2

4-methyl-1-(trimethylsiloxy)cyclohexanecarbonitrile

Conditions
ConditionsYield
With gold(III) chloride In dichloromethane at 20℃; for 0.5h;98%
With [In2(diphenic acid)3(1,10-phenanthroline)2]·H2O at 80℃; for 1h; Schlenk technique; Inert atmosphere;70%
With TBA8H2[(γ-SiYW10O36)2]*7H2O In 1,2-dichloro-ethane at 30℃; under 760.051 Torr; for 0.5h; Air atmosphere;97 %Chromat.
With [In4(OH)4((hexafluoroisopropylidene)bis benzoate)4(4,4'-bipyridine)] at 80℃; for 4h; Catalytic behavior; Schlenk technique; Inert atmosphere;> 99 %Spectr.
With [In(iminodiacetato)Cl] In neat (no solvent) at 25℃; for 4h; Catalytic behavior; Schlenk technique; Inert atmosphere;97 %Chromat.
1-methylcyclohexan-4-one
589-92-4

1-methylcyclohexan-4-one

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

(2S,4S)-2-((R)-hydroxy(2-nitrophenyl)methyl)-4-methylcyclohexan-1-one

(2S,4S)-2-((R)-hydroxy(2-nitrophenyl)methyl)-4-methylcyclohexan-1-one

Conditions
ConditionsYield
With O-(n-octanoyl)-L-threonine hydrochloride; water; triethylamine at 20℃; for 24h; optical yield given as %ee; enantioselective reaction;98%
With benzyl 3,4,6-tri-O-benzyl-2-deoxy-2-(L-prolylamino)-α-D-glucopyranoside at 0℃; for 8h; Aldol Condensation; enantioselective reaction;97%

589-92-4Relevant articles and documents

Studies Concerning the Factors Affecting the Formation of Cyclohexanone Intermediates in the Catalytic Hydrogenation of Phenols. I. Hydrogenation of p-Cresol over Various Pd-C Catalysts

Higashijima, Michio,Nishimura, Shigeo

, p. 824 - 830 (1992)

The catalytic hydrogenation of p-cresol with commercial Pd on active carbon (Pd-C), water-washed Pd-C (Pd-C-N), acid-treated Pd-C (Pd-C-A), and base-treated Pd-C (Pd-C-B) has been kinetically studied in cyclohexane as a solvent under 0.15-8.0 MPa hydrogen pressure at 80 deg C.Under each reaction condition, the hydrogenation rate constants for the cresol and the ketone intermediate, k1+k3 and k2, respectively, the relative reactivity of the ketone to the cresol (K) and the ratio of the adsorption coefficient of the ketone to that of the cresol (b2/b1) were determined of the basis of a Langmuir-Hinshelwood model.Regardless of the difference in the nature of the catalysts, hydrogenations with these catalysts always gave high selectivities of 0.85-1.0 for the formation of the ketone intermediate, and small values of 0.014-0.62 for the relative reactivity (K).The small values of K over Pd-C and Pd-C-B were shown to be mostly due to the small values of k2/(k1+k3).In contrast, even smaller values of K over Pd-C-N and Pd-C-A were found due to a great difference in the strength of adsorption between the cresol and the ketone intermediate.In general, both the values of K and k2/(k1+k3) increase with increasing hydrogen pressure.All of the experimental results show that both the alkaline impurities associated with catalyst preparation and the hydrogen pressure are the most important factors affecting the formation of the ketone intermediate.

(±)-Camphor sulfonic acid assisted IBX based oxidation of 1° and 2° alcohols

Kumar, Kamlesh,Joshi, Penny,Rawat, Diwan S

, (2021/09/02)

-

Visible-light photocatalytic selective oxidation of C(sp3)-H bonds by anion-cation dual-metal-site nanoscale localized carbon nitride

Duan, Limei,Li, Peihe,Li, Wanfei,Liu, Jinghai,Liu, Ying,Liu, Zhifei,Lu, Ye,Sarina, Sarina,Wang, Jinghui,Wang, Yin,Wang, Yingying,Zhu, Huaiyong

, p. 4429 - 4438 (2021/07/12)

Selective oxidation of C(sp3)-H bonds to carbonyl groups by abstracting H with a photoinduced highly active oxygen radical is an effective method used to give high value products. Here, we report a heterogeneous photocatalytic alkanes C-H bonds oxidation method under the irradiation of visible light (λ= 425 nm) at ambient temperature using an anion-cation dual-metal-site modulated carbon nitride. The optimized cation (C) of Fe3+or Ni2+, with an anion (A) of phosphotungstate (PW123?) constitutes the nanoscale dual-metal-site (DMS). With a Fe-PW12dual-metal-site as a model (FePW), we demonstrate a A-C DMS nanoscale localized carbon nitride (A-C/g-C3N4) exhibiting a highly enhanced photocatalytic activity with a high product yield (86% conversion), selectivity (up to 99%), and a wide functional group tolerance (52 examples). The carbon nitride performs the roles of both the visible light response, and improves the selectivity for the oxidation of C(sp3)-H bonds to carbonyl groups, along with the function of A-C DMS in promoting product yield. Mechanistic studies indicate that this reaction follows a radical pathway catalyzed by a photogenerated electron and hole on A-C/g-C3N4that is mediated by thetBuO˙ andtBuOO˙ radicals. Notably, a 10 g scale reaction was successfully achieved for alkane photocatalytic oxidation to the corresponding product with a good yield (80% conversion), and high selectivity (95%) under natural sunlight at ambient temperature. In addition, this A-C/g-C3N4photocatalyst is highly robust and can be reused at least six times and the activity is maintained.

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