4-Methylcyclohexanone supplier

Name
4-Methylcyclohexanone
EINECS 209-665-3
CAS No. 589-92-4
Article Data250
CAS DataBase
Density 0.912 g/cm³
Solubility Not miscible in water.
Melting Point -41 ºC
Formula C₇H₁₂O
Boiling Point 170 ºC at 760 mmHg
Molecular Weight 112.172
Flash Point 45.9 ºC
Transport Information UN 2297 3
Appearance Clear slightly yellow liquid.
Safety 16-36/37-23
Risk Codes R10;R20/21/22
Molecular Structure
Hazard Symbols Xi
Synonyms 4-Methyl-1-cyclohexanone;4-07-00-00044 (Beilstein Handbook Reference);NSC 3816;AI3-15916;BRN 0506746;Methyl-4 cyclohexanone-1;Methyl-4 cyclohexanone-1 [French];Cyclohexanone, 4-methyl-;
PSA 17.07000
LogP 1.76560

Synthetic route

: 589-91-3
p-methylcyclohexanol

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

Conditions

Conditions	Yield
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%

: 4994-13-2, 128925-57-5, 128925-58-6
4-methylcyclohexanone oxime

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

Conditions

Conditions	Yield
With bismuth(III) nitrate; silica gel In tetrahydrofuran; water for 2h; Heating;	97%

: 106-44-5
p-cresol

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

B: 7731-28-4
cis-4-methylcyclohexanol

C: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
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;

...Expand

: 18349-20-7
4-methylcyclohexanone dimethyl acetal

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

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate; silica gel In water for 0.0166667h; microwave irradiation;	88%

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

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

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate; silica gel In water for 0.05h; microwave irradiation;	82%
With sulfuric acid In tetrahydrofuran; water

: 106-44-5
p-cresol

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

Conditions

Conditions	Yield
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;

: 5718-78-5
p-4(8)-Menthene oxide

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

Conditions

Conditions	Yield
With jones' reagent In acetone at 15 - 20℃; for 0.5h;	80%

: 92377-01-0
1,2-bis(4-methylcyclohexylidene)hydrazine

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

Conditions

Conditions	Yield
With HOF* CH3CN In dichloromethane at 0℃; for 0.0166667h;	80%

: 589-91-3
p-methylcyclohexanol

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

B: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
With dimethyl sulfoxide; triethylamine; trichloromethyl chloroformate In dichloromethane	71%
With potassium dichromate; sulfuric acid
With chromium(VI) oxide

: 104-93-8
4-Methylanisole

A: 106-44-5
p-cresol

B: 75337-05-2, 79980-78-2, 101758-35-4, 5515-76-4
4-methyl-2-cyclohexenone

C: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium In tetrahydrofuran; ethanol at -30℃; for 2h;	A 41% B 50% C 4%

...Expand

: 25904-15-8
cis-1-Methoxy-4-methylcyclohexane

A: 2549-42-0, 18951-91-2, 18951-92-3, 116836-72-7
5-methyloxepan-2-one

B: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
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

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

B: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
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%

: 589-91-3
p-methylcyclohexanol

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

B: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
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%

: 82166-21-0
methyl cyclohexane

A: 590-67-0
1-Methylcyclohexanol

B: 589-92-4
1-methylcyclohexan-4-one

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

Conditions

Conditions	Yield
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;

...Expand

: 249904-46-9
1-Nitrooxy-bicyclo[2.2.1]heptane

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

B: 51566-98-4
1-norbornyl alcohol

C: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
With azobisisobutyronitrile; tri-n-butyl-tin hydride In benzene for 48h; Ring cleavage; Heating;	A n/a B 3% C n/a

...Expand

: 591-47-9
4-methylcyclohexene

A: 589-92-4
1-methylcyclohexan-4-one

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

Conditions

Conditions	Yield
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;

: 36099-51-1, 103189-46-4, 103189-47-5
3-methyl-7-oxabicyclo[4.1.0]heptane

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

B: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
With kieselguhr at 220 - 230℃;

: 7731-28-4
cis-4-methylcyclohexanol

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

Conditions

Conditions	Yield
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;

: 52662-20-1
methoxy-1 methyl-4 cyclohexene-1

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

Conditions

Conditions	Yield
Hydrolysis;

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

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

Conditions

Conditions	Yield
With sulfuric acid at -10℃;

: 94092-43-0
1-hydroxy-4-methyl-cyclohexanecarboxylic acid-(4-methyl-cyclohex-1-enyl ester)

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

B: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
With potassium hydroxide substance of mp: 82 degree;

: 64-17-5
ethanol

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

A: 74-90-8
hydrogen cyanide

B: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
at 25℃; Equilibrium constant;

...Expand

: 67-56-1
methanol

: 104-93-8
4-Methylanisole

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

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

C: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
Yield given. Multistep reaction;

...Expand

: 104-93-8
4-Methylanisole

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

B: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
1) Birch reduction, 2) acid hydrolysis; Multistep reaction;

: 106-44-5
p-cresol

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

B: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
With oxalic acid Multistep reaction;

: 109-74-0
propyl cyanide

: 589-91-3
p-methylcyclohexanol

A: 589-92-4
1-methylcyclohexan-4-one

B: N-butyl-4-methylcyclohexylamine

C: N-butyl-4-methylcyclohexylamine

D: trans-N,N-dibutyl-4-methylcyclohexylamine

E: cis-N,N-dibutyl-4-methylcyclohexylamine

F: 4,4'-dimethyldicyclohexylamine

Conditions

Conditions	Yield
aluminum oxide; lithium hydroxide; copper at 220℃; under 11400 Torr; for 0.3h; Product distribution; Mechanism;

...Expand

: 589-91-3
p-methylcyclohexanol

A: 589-92-4
1-methylcyclohexan-4-one

B: 4-methyl-6-chlorohexanal

Conditions

Conditions	Yield
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.

: 589-38-8
n-hexan-3-one

: 4-Methyl-cyclohexylidene-oxonium

A: 83238-66-8
protonated 3-hexanone

B: 589-92-4
1-methylcyclohexan-4-one

Conditions

Conditions	Yield
Equilibrium constant; Thermodynamic data; Gas phase. Determ. by ICR spect.;

...Expand

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

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

Conditions

Conditions	Yield
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

: 75-77-4
chloro-trimethyl-silane

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

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

Conditions

Conditions	Yield
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%

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

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

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1.5h;	100%
With triethylamine In dichloromethane for 1h;

: 100-52-7
benzaldehyde

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

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

Conditions

Conditions	Yield
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℃;

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

: 620-93-9
di-p-tolylamine

Conditions

Conditions	Yield
	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.

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

: 2549-42-0, 18951-91-2, 18951-92-3, 116836-72-7
5-methyloxepan-2-one

Conditions

Conditions	Yield
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%

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

: 589-91-3
p-methylcyclohexanol

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
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

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

: 100-63-0
phenylhydrazine

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

Conditions

Conditions	Yield
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%

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

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

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

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
With water-d2; sodium carbonate at 120℃; for 16h; Sealed tube;	99%
With water-d2; base

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

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

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	99%
With triethylamine In dichloromethane for 0.5h;	99%

: 610-15-1
2-nitrobenzamide

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

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

Conditions

Conditions	Yield
With tin(ll) chloride In ethanol; water at 20℃; for 2h;	99%

: 555-16-8
4-nitrobenzaldehdye

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

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

Conditions

Conditions	Yield
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%

: 555-16-8
4-nitrobenzaldehdye

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

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

Conditions

Conditions	Yield
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%

: 96534-02-0
3-(diethyoxyphosphorylmethyl)benzoic acid methyl ester

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

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

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	99%

: 27032-63-9
5-chloro-pyridin-2-yl hydrazine

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

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

Conditions

Conditions	Yield
In ethanol for 0.5h; Reflux;	99%

: 6329-74-4
5-bromo-2-hydroxybenzamide

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

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

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 8h; Reflux; Dean-Stark;	99%

: 100-52-7
benzaldehyde

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

: 62-53-3
aniline

: C20H23NO

Conditions

Conditions	Yield
With core-shell Fe3O4/saponin/Cd nanoparticles In ethanol at 20℃; for 0.916667h; Mannich Aminomethylation;	99%

...Expand

: 99-99-0
1-methyl-4-nitrobenzene

: 106-49-0
p-toluidine

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

: 620-93-9
di-p-tolylamine

Conditions

Conditions	Yield
palladium-carbon In water; N,N-dimethyl-formamide; benzene	98.6%
palladium-carbon In water; N,N-dimethyl-formamide; benzene	98.6%

...Expand

: 107-21-1
ethylene glycol

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

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

Conditions

Conditions	Yield
sulfonated charcoal In benzene Heating;	98%
With iodine at 20℃; Ionic liquid;	94%
With iodine for 16h;	90%

: 67461-24-9
3-methoxy-1,5-dihydro-3H-2,4-benzodioxepine

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

: 125426-00-8
C15H20O2

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In 1,2-dimethoxyethane for 0.5h; Ambient temperature;	98%

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

: 612-14-6
phthalyl alcohol

: 125426-00-8
C15H20O2

Conditions

Conditions	Yield
sulfonated charcoal In benzene Heating;	98%

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

: 105-56-6
ethyl 2-cyanoacetate

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

Conditions

Conditions	Yield
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%

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

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

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

Conditions

Conditions	Yield
In sulfolane for 2h; Heating;	98%

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

: 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

Conditions

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

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

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

Conditions

Conditions	Yield
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%

: 7677-24-9
trimethylsilyl cyanide

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

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

Conditions

Conditions	Yield
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.

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

: 552-89-6
2-nitro-benzaldehyde

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

Conditions

Conditions	Yield
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%

4-Methylcyclohexanone Chemical Properties

IUPAC Name: 4-Methylcyclohexan-1-one
Synonyms of 4-Methylcyclohexanone (CAS NO.589-92-4): 4-07-00-00044 (Beilstein Handbook Reference) ; 4-Methyl-1-cyclohexanone ; AI3-15916 ; BRN 0506746 ; EINECS 209-665-3 ; Methyl-4 cyclohexanone-1 ; Methyl-4 cyclohexanone-1 [French] ; NSC 3816 ; Cyclohexanone, 4-methyl-
CAS NO: 589-92-4
Molecular Formula: C₇H₁₂O
Molecular Weight: 112.1696
Molecular Structure:

Melting Point: -41 °C
Polar Surface Area: 17.07 Å²
Index of Refraction: 1.441
Molar Refractivity: 32.5 cm³
Molar Volume: 122.9 cm³
Surface Tension: 28.4 dyne/cm
Density: 0.912 g/cm³
Flash Point: 45.9 °C
Enthalpy of Vaporization: 40.64 kJ/mol
Boiling Point: 170 °C at 760 mmHg
Vapour Pressure: 1.5 mmHg at 25°C

4-Methylcyclohexanone Uses

4-Methylcyclohexanone (CAS NO.589-92-4) is mainly used as intermediates of CCNU and it can also be used as a solvent.

4-Methylcyclohexanone Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	intravenous	370mg/kg (370mg/kg)	CARDIAC: CHANGE IN RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 236, Pg. 633, 1953.
mouse	LD50	oral	1600mg/kg (1600mg/kg)		"Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4783, 1982.
rat	LD50	oral	800mg/kg (800mg/kg)		"Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4783, 1982.

4-Methylcyclohexanone Consensus Reports

Reported in EPA TSCA Inventory.

4-Methylcyclohexanone Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. Mixture with nitric acid explodes when heated to 75°C. When heated to decomposition it emits acrid smoke and irritating fumes.

Hazard Codes of 4-Methylcyclohexanone (CAS NO.589-92-4): Harmful Xn,Xi
Risk Statements: 10-20/21/22
R10:Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 16-36/37-23
S16:Keep away from sources of ignition.
S36/37:Wear suitable protective clothing and gloves.
S23:Do not breathe vapour.
RIDADR: UN 2297 3/PG 3
WGK Germany: 1
Hazard Note: Irritant
HazardClass: 3
PackingGroup: III
HS Code: 29142200

4-Methylcyclohexanone Analytical Methods

For occupational chemical analysis use NIOSH: Methylcyclohexanone, 2521.

Product Name

4-Methylcyclohexanone

Synthetic route

4-Methylcyclohexanone Chemical Properties

4-Methylcyclohexanone Uses

4-Methylcyclohexanone Toxicity Data With Reference

4-Methylcyclohexanone Consensus Reports

4-Methylcyclohexanone Safety Profile

4-Methylcyclohexanone Analytical Methods

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