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589-92-4

Basic Information
CAS No.: 589-92-4
Name: 4-Methylcyclohexanone
Article Data: 250
Molecular Structure:
Molecular Structure of 589-92-4 (4-Methylcyclohexanone)
Formula: C7H12O
Molecular Weight: 112.172
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-;
EINECS: 209-665-3
Density: 0.912 g/cm3
Melting Point: -41 ºC
Boiling Point: 170 ºC at 760 mmHg
Flash Point: 45.9 ºC
Solubility: Not miscible in water.
Appearance: Clear slightly yellow liquid.
Hazard Symbols: IrritantXi
Risk Codes: R10;R20/21/22   
Safety: 16-36/37-23
Transport Information: UN 2297 3
PSA: 17.07000
LogP: 1.76560
Synthetic route
589-91-3

p-methylcyclohexanol

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%
4994-13-2, 128925-57-5, 128925-58-6

4-methylcyclohexanone oxime

589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
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
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;
18349-20-7

4-methylcyclohexanone dimethyl acetal

589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
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
ConditionsYield
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
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;
5718-78-5

p-4(8)-Menthene oxide

589-92-4

1-methylcyclohexan-4-one

Conditions
ConditionsYield
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
ConditionsYield
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
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%
7731-29-5

trans-4-methylcyclohexan-1-ol

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
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Chemistry

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

Uses

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

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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): HarmfulXn,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

Analytical Methods

For occupational chemical analysis use NIOSH: Methylcyclohexanone, 2521.