Conditions | Yield |
---|---|
With zinc hydride In tetrahydrofuran for 24h; Ambient temperature; | 100% |
With sodium isopropylate; acetonitrile In isopropyl alcohol at 80℃; for 1h; Catalytic behavior; | 99% |
gadolinium(III) isopropoxide In isopropyl alcohol at 30℃; for 1h; | 98% |
2-(2-methyl-cyclohexyloxy)-tetrahydro-pyran
2-Methylcyclohexanol
Conditions | Yield |
---|---|
silica-supported prop-1-ylsulfonic acid In methanol | 99.6% |
With sulfuric acid; silica gel In methanol for 0.25h; Heating; | 80% |
With H14[NaP5W30O110] In methanol for 2h; Heating; | 97 % Chromat. |
Conditions | Yield |
---|---|
With hydrogen In water at 20℃; under 7500.75 Torr; for 6h; Autoclave; | 99.1% |
With hydrogen at 100℃; under 3750.38 Torr; for 3h; Reagent/catalyst; Pressure; Temperature; | 99% |
With nickel(II) oxide; hydrogen; palladium In hexane at 80℃; under 7500.75 Torr; for 10h; | 98% |
Conditions | Yield |
---|---|
With [{2-(2-pyridyl)benzimidazole}RuCl2(PPh3)2]; potassium hydroxide at 82℃; for 4h; | 97% |
With potassium hydroxide for 4h; Ambient temperature; | 8% |
Mechanism; Product distribution; Irradiation; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; triethylamine In water; acetonitrile Irradiation; | 94% |
With cobalt(II) tetrafluoroborate hexahydrate; hydrogen; zinc trifluoromethanesulfonate; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In 1,4-dioxane at 60℃; under 30003 Torr; for 20h; Autoclave; regioselective reaction; | 88 %Chromat. |
With ammonia borane; C28H28Cl2CoNP2; erbium(III) triflate In tetrahydrofuran at 55℃; for 8h; | 89 %Chromat. |
1,2-epoxy-3-methyl-cyclohexane
A
2-Methylcyclohexanol
B
m-methylcyclohexanol
Conditions | Yield |
---|---|
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane at 0℃; for 0.17h; Yields of byproduct given. Title compound not separated from byproducts; | A 93% B n/a |
With Li(1+)*C12H28AlO3(1-) In tetrahydrofuran; hexane at 0℃; for 0.17h; | A 93% B n/a |
Conditions | Yield |
---|---|
Stage #1: 1-methylcyclohex-1-ene With 1-bromo-butane; sodium tetrahydroborate; Aliquat 336 at 20℃; for 16h; Addition; Hydroboration; Stage #2: With sodium hydroxide; dihydrogen peroxide at 40℃; for 1h; Oxidation; | 78% |
With sodium tetrahydroborate; (2,3,7,8,12,13,17,18-octaethylporphyrinato)rhodium(III) chloride; oxygen In tetrahydrofuran at 20 - 25℃; for 50h; Product distribution; Mechanism; other olefins, diene and acetylenes, other rhodium porphyrin, other conc. of catalyst; | |
With sodium tetrahydroborate; oxygen; (2,3,7,8,12,13,17,18-octaethylporphyrinato)rhodium(III) chloride In tetrahydrofuran Ambient temperature; 48-130 h; Yield given; |
2-Trimethylsilanylmethyl-cyclohexanol
2-Methylcyclohexanol
Conditions | Yield |
---|---|
With potassium tert-butylate; 18-crown-6 ether In water; dimethyl sulfoxide at 80℃; for 12h; | 78% |
2-(6-Methyl-1-oxa-4-aza-spiro[4.5]dec-4-yl)-ethanol
A
2-Methylcyclohexanol
B
2-(7-Methyl-4,5,6,7-tetrahydro-indol-1-yl)-ethanol
C
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
With potassium hydroxide Heating; CH3ONa as reagent; | A n/a B 59% C n/a |
1,5-bis(bromomagnesio)hexane
formic acid ethyl ester
2-Methylcyclohexanol
Conditions | Yield |
---|---|
In tetrahydrofuran | 57% |
Conditions | Yield |
---|---|
With Cu2(OTf)2; (-)-(aR)-[1,1'-binaphthalene]-8,8'-diyl dimethylphosphoramidite In tetrahydrofuran at -78 - 20℃; Ring cleavage; methylation; | 45% |
Conditions | Yield |
---|---|
With [(hydrotris(3,5-diphenyl-pyrazol-1-yl)borate)FeII(benzilate)]; oxygen; scandium tris(trifluoromethanesulfonate) In benzene at 20℃; Inert atmosphere; | A 13% B 45% |
With [(hydrotris(3,5-diphenyl-pyrazol-1-yl)borate)FeII(benzilate)]; oxygen; pyridinium perchlorate In acetonitrile; benzene at 20℃; for 0.25h; Catalytic behavior; Reagent/catalyst; | A 15% B 44% |
With 2,6-dimethylpyridine; Cumene hydroperoxide; [FeII(1,1’-(((pyridin-2-ylmethyl)azanediyl)bis(ethane-2,1-diyl))bis(3-(tert-butyl)urea))(H2O)(trifluoromethanesulfonate)](trifluoromethanesulfonate) In acetonitrile at -20.16 - 9.84℃; for 1h; Catalytic behavior; Inert atmosphere; |
methyl cyclohexane
A
p-methylcyclohexanol
B
2-Methylcyclohexanol
C
1-Methylcyclohexanol
D
m-methylcyclohexanol
Conditions | Yield |
---|---|
With iodosylbenzene; 5,10,15,20-tetraphenyl-21 H,23-H-porphine manganese(III)chloride In benzene for 2h; Ambient temperature; pAr = 1 atm; Further byproducts given. Title compound not separated from byproducts; | A 18% B 20% C 24% D 3% |
With iodosylbenzene; 5,10,15,20-tetraphenyl-21 H,23-H-porphine manganese(III)chloride In benzene for 2h; Ambient temperature; pAr= 1 atm; Further byproducts given. Title compound not separated from byproducts; | A 18% B 20% C 24% D 3% |
With peracetic acid; tris(μ-oxo)di[(1,4,7-trimethyl-1,4,7-triazanonane)manganese(IV)] hexafluorophosphate In acetonitrile at 30℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given; |
2-Methylcyclohexanol
Conditions | Yield |
---|---|
With tetrahydrofuran; titanium(III) chloride; lithium for 40h; Heating; | 20% |
Conditions | Yield |
---|---|
at 24.9℃; Equilibrium constant; other temperatures; calculated values; | A 17% B 8.6% |
at 240 - 320℃; an metallbeschichtetem opt.-akt. Quarz; |
methyl magnesium iodide
trans-2-chlorocyclohexanol
A
2-Methylcyclohexanol
B
1-cyclopentylethan-1-ol
Conditions | Yield |
---|---|
With diethyl ether dl-trans-1-methyl-cyclohexanol-(2); |
Conditions | Yield |
---|---|
With ethanol; sodium | |
With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With manganese containing nickel catalyst at 170℃; Hydrogenation.unter Druck; d-cis-1-methyl-cyclohexanol-(2); | |
With manganese containing nickel catalyst at 170℃; Hydrogenation.unter Druck; l-cis-1-methyl-cyclohexanol-(2); |
2,2-bis(4-hydroxy-3-methylphenyl)propane
A
2-Methylcyclohexanol
B
4-isopropyl-2-methylcyclohexanol
Conditions | Yield |
---|---|
in Gegenwart eines Kupfer, Kobalt und Mangan enthaltenen Nickelkatalysators.Hydrogenation; |
diethyl ether
methyllithium
cyclohexane-1,2-epoxide
2-Methylcyclohexanol
2-Methylcyclohexanone
A
2-Methylcyclohexanol
B
3-methyl-2-oxo-cyclohexanecarbaldehyde
Conditions | Yield |
---|---|
With diethyl ether; sodium; formic acid ethyl ester dl-trans-1-methyl-cyclohexanol-(2); |
Conditions | Yield |
---|---|
With CuO/Cr2O3 at 250℃; Hydrogenation; |
1,2-epoxy-1-methylcyclohexane
A
2-Methylcyclohexanol
B
1-Methylcyclohexanol
Conditions | Yield |
---|---|
With sodium tert-pentoxide; sodium hydride; nickel dichloride In 1,2-dimethoxyethane at 65℃; for 40h; Yield given. Yields of byproduct given; |
1,2-epoxy-1-methylcyclohexane
A
2-Methylcyclohexanol
B
1-Methylcyclohexanol
(1S,2S)-2-Isopropoxy-2-methyl-cyclohexanol
(1R,2R)-2-Isopropoxy-1-methyl-cyclohexanol
Conditions | Yield |
---|---|
In isopropyl alcohol Irradiation; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile Irradiation; Yield given. Yields of byproduct given; |
2-methyl-2-cyclohexen-1-one
A
2-Methylcyclohexanol
B
2-methylcyclohex-2-en-1-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate; alpha cyclodextrin In water Product distribution; influence of other cyclodextrin on the reduction; | |
With sodium tetrahydroborate; β‐cyclodextrin In water for 24h; | A 35 % Chromat. B 65 % Chromat. |
With sodium tetrahydroborate In water Ambient temperature; | A 22 % Chromat. B 78 % Chromat. |
With sodium tetrahydroborate; alpha cyclodextrin In water for 24h; | A 10 % Chromat. B 90 % Chromat. |
2-methyl-2-cyclohexen-1-one
A
2-Methylcyclohexanol
B
2-methylcyclohex-2-en-1-ol
C
2-Methylcyclohexanone
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; cryptand 211 In tetrahydrofuran for 0.0833333h; Ambient temperature; Yield given. Yields of byproduct given; | |
With lithium aluminium tetrahydride In tetrahydrofuran for 0.0166667h; Ambient temperature; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With hydrogen; nickel In methanol at 170℃; under 114000 Torr; for 24h; Yield given; |
cyclohexane
methyl cyclohexane
A
p-methylcyclohexanol
B
2-Methylcyclohexanol
C
1-Methylcyclohexanol
D
m-methylcyclohexanol
E
2-Methylcyclohexanone
F
3-Methylcyclohexanone
Conditions | Yield |
---|---|
5,10,15,20-tetraphenyl-21 H,23-H-porphine manganese(III)chloride for 2h; Product distribution; Mechanism; Ambient temperature; variations of reagents, pO2, protective atmosphere; |
methyl cyclohexane
A
2-Methylcyclohexanol
B
1-Methylcyclohexanol
C
1-methylcyclohexan-4-one
D
3-Methylcyclohexanone
Conditions | Yield |
---|---|
With hydrogenchloride; oxygen; sodium L-ascorbate; 5,10,15,20-tetraphenyl-21 H,23-H-porphine manganese(III)chloride In benzene Ambient temperature; pH=8.5, pO2= 1 atm; Further byproducts given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium tungstate In tert-butyl alcohol at 90℃; for 0.5h; | 100% |
With jones reagent; silica gel In dichloromethane for 0.0833333h; | 99% |
With silica-supported Jones reagent In dichloromethane for 0.00269444h; | 99.7% |
3,4-dihydro-2H-pyran
2-Methylcyclohexanol
2-(2-methyl-cyclohexyloxy)-tetrahydro-pyran
Conditions | Yield |
---|---|
silica-supported prop-1-ylsulfonic acid In acetonitrile for 0.166667h; | 99.8% |
With sulfuric acid; silica gel for 0.0166667h; Irradiation; microwave; | 80% |
With H14[NaP5W30O110] In dichloromethane for 1h; Heating; | 94 % Chromat. |
Conditions | Yield |
---|---|
platinum; potassium oxide at 360℃; | A 98% B 2% |
platinum; potassium oxide at 360℃; Product distribution; other content of catalyst; | A 98% B 2% |
2-Methylcyclohexanol
p-toluenesulfonyl chloride
Toluene-4-sulfonic acid 2-methyl-cyclohexyl ester
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In ethyl acetate at 0 - 20℃; for 96h; | 95% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane In acetonitrile for 2h; | 91% |
2-Methylcyclohexanol
2,2,6-trichloro-6-methylcyclohexanone
Conditions | Yield |
---|---|
With chlorine In N,N-dimethyl-formamide at 35 - 45℃; for 3h; | 91% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 100 - 124℃; for 3h; Temperature; | 89.8% |
With sulfuric acid at 100 - 110℃; |
2-Methylcyclohexanol
chloroacetic acid
(2-methylcyclohexyl)oxyacetic acid
Conditions | Yield |
---|---|
Stage #1: 2-Methylcyclohexanol With lithium In tetrahydrofuran for 16h; Inert atmosphere; Reflux; Stage #2: chloroacetic acid In tetrahydrofuran for 6h; Inert atmosphere; Reflux; | 89% |
2-Methylcyclohexanol
1,1,1,3,3,3-hexamethyl-disilazane
Trimethyl-(2-methyl-cyclohexyloxy)-silane
Conditions | Yield |
---|---|
With potassium fluoride incorporated on clinoptilolite nanoparticles In dichloromethane at 20℃; for 1.25h; chemoselective reaction; | 86% |
With sulfonic acid functionalized silica In dichloromethane at 20℃; for 1h; | 90 % Chromat. |
With [Ti(IV)(salophen)(OTf)2] In dichloromethane at 20℃; for 0.25h; | 98 %Chromat. |
2-Methylcyclohexanol
tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate
tert-butyl 8-[(2-methylcyclohexyl)oxy]-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate
Conditions | Yield |
---|---|
Stage #1: 2-Methylcyclohexanol With sodium hydride In toluene at 70℃; for 0.25h; Inert atmosphere; Stage #2: tert-Butyl 8-chloro-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 2h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With pyridine In diethyl ether at 18 - 23℃; | 80% |
2-Methylcyclohexanol
ethyl 6-benzyl-2-(benzyloxy)-4-hydroxynicotinate
ethyl 6-benzyl-2-(benzyloxy)-4-(2-methylcyclohexyloxy)nicotinate
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 20h; | 80% |
2-Methylcyclohexanol
3,3,4-trichloro-3-butenoyl chloride
Conditions | Yield |
---|---|
With pyridine In diethyl ether at 20 - 23℃; for 22h; | 77% |
2-Methylcyclohexanol
ethyl 2-(benzyloxy)-4-hydroxy-6-phenethylnicotinate
ethyl 2-(benzyloxy)-4-(2-methylcyclohexyloxy)-6-phenethyl nicotinate
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 20h; | 76% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu Displacement; | 51% |
2-Methylcyclohexanol
2-Chlorocyclohexanone
6-methyl-1,2,3,4-tetrahydrodibenzo[b,d]furan
Conditions | Yield |
---|---|
With titanium tetrachloride In 2,2,2-trifluoroethanol Inert atmosphere; Reflux; | 76% |
chloro-trimethyl-silane
2-Methylcyclohexanol
Trimethyl-(2-methyl-cyclohexyloxy)-silane
Conditions | Yield |
---|---|
With urea at 20℃; for 4h; | 73.4% |
2-Methylcyclohexanol
2,2,2-trichloroethyl heptanoate
Heptanoic acid (R)-2-methyl-cyclohexyl ester
Conditions | Yield |
---|---|
With porcine pancreatic lipase In n-heptane at 60℃; for 96h; | 72% |
Conditions | Yield |
---|---|
In hexane at -40 - 20℃; for 3h; Inert atmosphere; Schlenk technique; | 72% |
Conditions | Yield |
---|---|
With sulfuric acid at 20℃; Inert atmosphere; | 70% |
With sulfuric acid |
Conditions | Yield |
---|---|
With cerium(III) chloride heptahydrate; tetrabutyl-ammonium chloride In acetonitrile for 19h; Inert atmosphere; Irradiation; | 68% |
Conditions | Yield |
---|---|
With 1,3-dicyclohexylimidazol-2-ylidene at 25℃; for 0.25h; | 67% |
Conditions | Yield |
---|---|
With sulfuric acid at 25 - 30℃; | 66% |
The 2-Methylcyclohexanol with CAS registry number of 583-59-5 is also known as Cyclohexanol, 2-methyl-. The IUPAC name is 2-Methylcyclohexan-1-ol. It belongs to product categories of Industrial/Fine Chemicals. Its EINECS registry number is 209-512-0. In addition, the formula is C7H14O and the molecular weight is 114.21. This chemical is a colourless viscous liquid with an aromatic odour that may cause damage to health. It is slightly soluble in water and should be sealed in cool, dry place. What's more, this chemical can be used as organic chemical, solvent, lubricant additive, auxiliary and antioxidant. As it is harmful by inhalation, avoid contact with skin and eyes when using it.
Physical properties about 2-Methylcyclohexanol are: (1)ACD/LogP: 1.83; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.83; (4)ACD/LogD (pH 7.4): 1.83; (5)ACD/BCF (pH 5.5): 14.55; (6)ACD/BCF (pH 7.4): 14.55; (7)ACD/KOC (pH 5.5): 236.62; (8)ACD/KOC (pH 7.4): 236.62; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.462; (13)Molar Refractivity: 33.96 cm3; (14)Molar Volume: 123.4 cm3; (15)Surface Tension: 28.9 dyne/cm; (16)Density: 0.925 g/cm3; (17)Flash Point: 58.9 °C; (18)Enthalpy of Vaporization: 47.36 kJ/mol; (19)Boiling Point: 170.3 °C at 760 mmHg; (20)Vapour Pressure: 0.475 mmHg at 25 °C.
Preparation of 2-Methylcyclohexanol: it is prepared by reaction of 1,2-epoxy-1-methyl-cyclohexane. The reaction needs reagents Et3N, NaBH4 and solvents acetonitrile, H2O with other condition of irradiation. The yield is about 94 %.
Uses of 2-Methylcyclohexanol: it is used to produce acetic acid-(2-methyl-cyclohexyl ester) by reaction with acetic acid anhydride. The reaction occurs with reagent chlorotrimethylsilane and solvent acetonitrile for 2 hours. The yield is about 91 %.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC1CCCCC1O
2. InChI: InChI=1S/C7H14O/c1-6-4-2-3-5-7(6)8/h6-8H,2-5H2,1H3
3. InChIKey: NDVWOBYBJYUSMF-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intramuscular | 1gm/kg (1000mg/kg) | Journal of Scientific and Industrial Research, Section C: Biological Sciences. Vol. 21, Pg. 342, 1962. |
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