Conditions | Yield |
---|---|
With [(C18H37)2(CH3)2N]3[SiO4H(WO5)3]; dihydrogen peroxide In ethyl acetate at 59.84℃; for 2h; Green chemistry; | 99% |
With tert.-butylhydroperoxide at 79.84℃; Reagent/catalyst; Temperature; Green chemistry; | 95% |
With 3-chloro-benzenecarboperoxoic acid In benzene at 20℃; for 0.5h; | 94% |
1,1,3,3-tetrachloropropanone
4-ethenylcyclohexene
A
4-vinylcyclohexene dioxide
B
1,2-Epoxy-4-vinylcyclohexane
C
7,8-Epoxy-1-Cyclohexene
D
tetrachloroacetone hydrate
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; dihydrogen peroxide In chloroform for 24h; Ambient temperature; | A 2% B 60% C 2.5% D n/a |
With disodium hydrogenphosphate; dihydrogen peroxide In chloroform for 24h; Ambient temperature; | A 2% B 60% C 1.5% D n/a |
4-ethenylcyclohexene
A
1,2-Epoxy-4-vinylcyclohexane
B
3,4-dihydroxy-1-vinylcyclohexane
Conditions | Yield |
---|---|
With dihydrogen peroxide; magnesium sulfate; methyltrioxorhenium(VII) In tert-butyl alcohol at 15℃; for 2h; | A 50% B 40% |
With dihydrogen peroxide; magnesium sulfate; methyltrioxorhenium(VII) In tert-butyl alcohol at 15℃; for 2h; | A 40% B 50% |
With dihydrogen peroxide; acetic acid In water at 70℃; for 4h; Temperature; |
4-ethenylcyclohexene
A
4-vinylcyclohexene dioxide
B
1,2-Epoxy-4-vinylcyclohexane
C
7,8-Epoxy-1-Cyclohexene
Conditions | Yield |
---|---|
With dimethylammonium tetrakis(diperoxotungsto)phosphate; dihydrogen peroxide In benzene at 60℃; for 1h; | A 3 % Chromat. B 83 % Chromat. C 2 % Chromat. |
With dihydrogen peroxide; cetylpyridinium bromide; H3PMo10W2O40 In acetonitrile at 60℃; for 3h; Product distribution; Further Variations:; Catalysts; Solvents; Temperatures; |
4-ethenylcyclohexene
A
1,2-Epoxy-4-vinylcyclohexane
B
7,8-Epoxy-1-Cyclohexene
C
3,4-dihydroxy-1-vinylcyclohexane
Conditions | Yield |
---|---|
With [π-C5H5N(+)(CH2)15CH3]3(PMo12O40)(3-); dihydrogen peroxide; magnesium sulfate In chloroform at 60℃; for 24h; Yield given. Yields of byproduct given; |
4-ethenylcyclohexene
A
1,2-Epoxy-4-vinylcyclohexane
B
4-Vinylcyclohex-1-en-4-ol
trans-4-Vinylcyclohex-1-en-3-ol
trans-4-Vinylcyclohex-1-en-6-ol
cis-4-Vinylcyclohex-1-en-6-ol
cis-3-Vinylcyclohex-1-en-6-ol
Conditions | Yield |
---|---|
With oxygen; sodium sulfite Product distribution; multistep reaction: 1) 80 deg C, 15 h, 101.3 kPa; | A 0.6 % Chromat. B 15.2 % Chromat. C 15.1 % Chromat. D 22.6 % Chromat. E 45.0 % Chromat. F n/a |
4-ethenylcyclohexene
A
1,2-Epoxy-4-vinylcyclohexane
trans-3-Hydroperoxy-4-vinylcyclohex-1-en
cis-6-Hydroperoxy-3-vinylcyclohex-1-en
D
4-Hydroperoxy-4-vinylcyclohex-1-en
trans-6-Hydroperoxy-4-vinylcyclohex-1-en
cis-6-Hydroperoxy-4-vinylcyclohex-1-en
Conditions | Yield |
---|---|
With oxygen at 80℃; under 759.8 Torr; for 15h; Product distribution; autoxidation; | A 4 % Chromat. B 13 % Chromat. C 6 % Chromat. D 13 % Chromat. E 18 % Chromat. F 45 % Chromat. |
4-ethenylcyclohexene
acetic acid
A
1,2-Epoxy-4-vinylcyclohexane
B
3,4-dihydroxy-1-vinylcyclohexane
Conditions | Yield |
---|---|
With MoOBr3; dihydrogen peroxide at 70℃; for 6h; Product distribution; other cyclohexene derivatives; other molybdenum complexes; |
4-ethenylcyclohexene
A
4-vinylcyclohexene dioxide
B
1,2-Epoxy-4-vinylcyclohexane
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; silica gel; molybdenum trioxide In decane at 50℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With air; bis(hexafluoroacetylacetonato)cobalt; isobutyraldehyde In 1,2-dichloro-ethane at 20℃; under 7600 Torr; for 24h; Product distribution; Further Variations:; Reagents; Pressures; | A 20 % Chromat. B 80 % Chromat. |
With air; bis(hexafluoroacetylacetonato)cobalt; isobutyraldehyde In 1,2-dichloro-ethane at 20℃; under 7600 Torr; for 24h; | A 20 % Chromat. B 80 % Chromat. |
With [Mn(CF3SO3)2(H,MePyTACN)]; dihydrogen peroxide; acetic acid In acetonitrile at 0℃; for 1.5h; chemoselective reaction; |
1,2-Epoxy-4-vinylcyclohexane
Conditions | Yield |
---|---|
With Perbenzoic acid; chloroform |
4-ethenylcyclohexene
A
1,2-Epoxy-4-vinylcyclohexane
B
7,8-Epoxy-1-Cyclohexene
Conditions | Yield |
---|---|
With dihydrogen peroxide; TBA-[γ-SiW10O34(H2O)2]4- In acetonitrile at 31.85℃; for 4h; Product distribution; Further Variations:; Catalysts; Reagents; | A 94 % Chromat. B 4 % Chromat. |
With peracetic acid; Mn3(2-pyridinal-1-phenylethylimine)2(OAc)6 In acetonitrile at 25℃; for 0.3h; Title compound not separated from byproducts; | |
With dihydrogen peroxide; teterabutylammonium In acetonitrile at 31.85℃; for 4h; | |
With iodosylbenzene; iron(III) tetraphenylporphyrin In dichloromethane at 25℃; for 0.5h; Product distribution; Further Variations:; Catalysts; |
methanol
4-ethenylcyclohexene
A
4-vinylcyclohexene dioxide
B
1,2-Epoxy-4-vinylcyclohexane
C
7,8-Epoxy-1-Cyclohexene
D
cyclohex-3-enyl acetaldehyde
E
3-cyclohexenyl-2-ethanone
G
C9H16O2
Conditions | Yield |
---|---|
With dihydrogen peroxide In water at 64.84℃; for 2h; regioselective reaction; |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; 2BF4(1-)*C30H32N8O3Ru(2+) In dichloromethane at 20℃; for 24h; Inert atmosphere; Darkness; regioselective reaction; |
methanol
4-ethenylcyclohexene
A
4-vinylcyclohexene dioxide
B
1,2-Epoxy-4-vinylcyclohexane
C
7,8-Epoxy-1-Cyclohexene
E
C9H16O2
F
3-Cyclohexene-1-carboxaldehyde
Conditions | Yield |
---|---|
With dihydrogen peroxide In water at 65℃; for 1.5h; |
1,2-Epoxy-4-vinylcyclohexane
1,1,3,3-tetramethyl-1-(2-trimethylsilanylethyl)disiloxane
3-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanylethyl)disiloxanyl]ethyl}-7-oxabicyclo[4.1.0]heptane
Conditions | Yield |
---|---|
With buffer; Karstedt's catalyst In toluene at 80 - 90℃; | 100% |
With dihydrogen hexachloroplatinate at 75 - 85℃; for 2h; |
1,2-Epoxy-4-vinylcyclohexane
Triethoxysilane
(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)triethoxysilane
Conditions | Yield |
---|---|
With platinum-containing olefin organic polymer catalyst at 25℃; for 3h; | 99% |
With (TFAPDI)Co(2-ethylhexanoate)2 In neat (no solvent) at 23℃; for 1h; | 96% |
With (1-mesityl-3-methylimidazol-2-ylidene)Co(N(SiMe3)2)2 In neat (no solvent) at 20℃; for 8h; Inert atmosphere; Glovebox; chemoselective reaction; | 94% |
With graphene nanoplates-supported platinum nanoparticles In neat (no solvent) at 80℃; for 2h; Catalytic behavior; | 92% |
Conditions | Yield |
---|---|
With graphene nanoplates-supported platinum nanoparticles In neat (no solvent) at 80℃; for 2h; Catalytic behavior; | 98% |
With dihydrogen hexachloroplatinate at 75 - 85℃; for 2h; | 96% |
With dihydrogen hexachloroplatinate at 75 - 85℃; | 96% |
1,2-Epoxy-4-vinylcyclohexane
Conditions | Yield |
---|---|
With platinum In benzene at 20℃; for 34h; | 98% |
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer In neat (no solvent) at 50℃; for 2h; | 98% |
1,2-Epoxy-4-vinylcyclohexane
1,1,3,3-Tetramethyldisiloxane
1,3-bis(2(3,4-epoxycyclohexyl)ethyl)-1,1,3,3-tetramethyldisiloxane
Conditions | Yield |
---|---|
In ethanol; toluene at 65℃; for 0.333333h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; Molecular sieve; Microwave irradiation; | 97.8% |
In tetrahydrofuran; ethanol at 75℃; for 4h; Reagent/catalyst; Temperature; Solvent; Molecular sieve; Inert atmosphere; | 96.9% |
2C8H18S*3Cl(1-)*Rh(3+) In ethanol; hexane at 82℃; for 3h; Heating / reflux; |
1,2-Epoxy-4-vinylcyclohexane
1,1,3,3,5,5,7,7-octamethyltetrasiloxane
(1,7-bis(1,2-epoxycyclohexyl-4-ethyl))-1,1,3,3,5,5,7,7-octamethyltetrasiloxane
Conditions | Yield |
---|---|
polymer-bound Wilkinson's catalyst In toluene at 100 - 115℃; for 48h; Heating / reflux; | 96% |
1,2-Epoxy-4-vinylcyclohexane
3,4-dihydroxy-1-vinylcyclohexane
Conditions | Yield |
---|---|
With water at 20℃; for 5h; Conversion of starting material; | 95% |
With water; Amberlyst 15 resin at 20℃; for 24h; Conversion of starting material; | 95% |
With sulfuric acid In water at 20℃; | 85% |
1,2-Epoxy-4-vinylcyclohexane
1-dimethylsiloxy-3,5,7,9,11,13,15-heptakis(trimethylsiloxy)pentacyclo[9.5.1.1(3,9).1(5,15).1(7,13)]-octasiloxane
Conditions | Yield |
---|---|
1,3-di(η2-vinyl)-1.1.3.3-tetramethyldisiloxane platinum(0) In toluene at 20℃; for 2h; | 95% |
Conditions | Yield |
---|---|
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 40℃; for 12h; Schlenk technique; | 95% |
1,2-Epoxy-4-vinylcyclohexane
Conditions | Yield |
---|---|
With 2,6-bis[1-(2,6-diisopropylphenylimino)ethyl]pyridine cobalt(II) dichloride; diethoxymethylane; sodium triethylborohydride In toluene at -78 - 20℃; for 5h; | 95% |
1,2-Epoxy-4-vinylcyclohexane
dimethylmethoxysilane
Conditions | Yield |
---|---|
With C24H30ClN3NiO2; sodium t-butanolate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; Glovebox; | 93% |
1,2-Epoxy-4-vinylcyclohexane
Conditions | Yield |
---|---|
With aluminum oxide; thiourea In water at 25℃; for 2h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With potassium hydroxide In toluene at 20 - 105℃; for 18h; Reagent/catalyst; Temperature; Solvent; | 93% |
1,2-Epoxy-4-vinylcyclohexane
Conditions | Yield |
---|---|
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 90℃; for 3h; | 92% |
Conditions | Yield |
---|---|
With C77H70N2OPtSi2 In toluene at 80℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction; | 91% |
1,2-Epoxy-4-vinylcyclohexane
trimethoxysilane
trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane
Conditions | Yield |
---|---|
chloroplatinic acid | 90% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In neat (no solvent) at 100℃; for 18h; chemoselective reaction; | 90% |
In neat (no solvent) at 90℃; under 3750.38 Torr; for 24h; Autoclave; | 83% |
With C37H41FeN6O2(1+)*I(1-); bis(triphenylphosphine)iminium chloride In neat (no solvent) at 80℃; under 3750.38 Torr; for 24h; Autoclave; | 76% |
Conditions | Yield |
---|---|
With C20H13FeN2O5; tetrabutylammomium bromide at 100℃; under 3750.38 - 7500.75 Torr; for 18h; Sealed tube; | 90% |
Conditions | Yield |
---|---|
Stage #1: 4-allylguaiacol; octakis(dimethylsiloxy)octasilsesquioxane With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Karstedt's catalyst In toluene at 90℃; Stage #2: 1,2-Epoxy-4-vinylcyclohexane In toluene at 90℃; | 89% |
Conditions | Yield |
---|---|
With [(N(C6H4N(CH3)2)2)Ni(OCH3)] In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; Glovebox; Sealed tube; chemoselective reaction; | 88% |
Stage #1: 1,2-Epoxy-4-vinylcyclohexane; diphenylsilane With bis(acetylacetonate)nickel(II) In tetrahydrofuran at 20℃; for 0.0166667h; Inert atmosphere; Stage #2: With sodium triethylborohydride In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; | 83% |
With sodium methylate In tetrahydrofuran Heating; | 76% |
Conditions | Yield |
---|---|
Stage #1: 1,2-Epoxy-4-vinylcyclohexane; octakis(dimethylsiloxy)octasilsesquioxane With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Karstedt's catalyst In toluene at 90℃; Stage #2: Triethoxyvinylsilane In toluene at 90℃; | 88% |
Conditions | Yield |
---|---|
Stage #1: Methyl 10-undecenoate; octakis(dimethylsiloxy)octasilsesquioxane With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Karstedt's catalyst In toluene at 90℃; Stage #2: 1,2-Epoxy-4-vinylcyclohexane In toluene at 90℃; | 87% |
Conditions | Yield |
---|---|
With nickel(II) chloride hexahydrate; potassium tert-butylate In tetrahydrofuran at -30℃; for 1h; Schlenk technique; Inert atmosphere; Sealed tube; | 87% |
Conditions | Yield |
---|---|
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tetramethylammonium formiate; triphenylphosphine In water; N,N-dimethyl-formamide at 80℃; for 4h; Heck Reaction; regioselective reaction; | 86% |
Conditions | Yield |
---|---|
With C21H12Cl6NO4V; tetrabutylammomium bromide In neat (no solvent) at 85℃; under 7500.75 Torr; for 18h; | 82% |
With calcium iodide In neat (no solvent) at 70℃; under 15001.5 Torr; for 24h; diastereoselective reaction; | 77% |
With C68H70Co3N16O8; tetrabutyl-ammonium chloride In neat (no solvent) at 80℃; under 15514.9 Torr; for 4h; Inert atmosphere; Autoclave; |
Conditions | Yield |
---|---|
Stage #1: 3,7-dimethylocta-1,6-dien-3-ol; octakis(dimethylsiloxy)octasilsesquioxane With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Karstedt's catalyst In toluene at 90℃; Stage #2: 1,2-Epoxy-4-vinylcyclohexane In toluene at 90℃; | 82% |
1,2-Epoxy-4-vinylcyclohexane
Conditions | Yield |
---|---|
With oxygen; copper(II) bis(trifluoromethanesulfonate); dimethyl sulfoxide; bismuth at 100℃; for 1.3h; | 77% |
1,2-Epoxy-4-vinylcyclohexane
Dimethylphenylsilane
<2-(3,4-Epoxy-cyclohexyl)-aethyl>-dimethyl-phenyl-silan
Conditions | Yield |
---|---|
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; N-ethyl-N,N-diisopropylamine; triisopropylsilanethiol In 1,4-dioxane at 20℃; Schlenk technique; Sealed tube; Inert atmosphere; Irradiation; | 77% |
Stage #1: 1,2-Epoxy-4-vinylcyclohexane; Dimethylphenylsilane With C11H13Cl2CoN5 In toluene at 80℃; for 0.5h; Schlenk technique; Stage #2: With sodium triethylborohydride In toluene at 80℃; for 24h; Schlenk technique; | |
With C77H70N2OPtSi2 In toluene at 80℃; for 8h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique; regioselective reaction; | 99 %Chromat. |
The molecular structure of 1,2-Epoxy-4-vinylcyclohexane (CAS NO.106-86-5):
IUPAC Name: 3-Ethenyl-7-oxabicyclo[4.1.0]heptane
Molecular Weight: 124.18028 g/mol
Molecular Formula: C8H12O
Density: 1.06 g/cm3
Boiling Point: 169 °C at 760 mmHg
Flash Point: 48.1 °C
Index of Refraction: 1.564
Molar Refractivity: 38.1 cm3
Molar Volume: 117.1 cm3
Surface Tension: 36.7 dyne/cm
Enthalpy of Vaporization: 38.88 kJ/mol
Vapour Pressure: 2.09 mmHg at 25 °C
XLogP3-AA: 1.7
H-Bond Acceptor: 1
Rotatable Bond Count: 1
Exact Mass: 124.088815
MonoIsotopic Mass: 124.088815
Topological Polar Surface Area: 12.5
Heavy Atom Count: 9
Canonical SMILES: C=CC1CCC2C(C1)O2
InChI: InChI=1S/C8H12O/c1-2-6-3-4-7-8(5-6)9-7/h2,6-8H,1,3-5H2
InChIKey: SLJFKNONPLNAPF-UHFFFAOYSA-N
EINECS: 203-436-1
Product Categories of 1,2-Epoxy-4-vinylcyclohexane (CAS NO.106-86-5): Industrial/Fine Chemicals; Monomers; Polymer Science; Vinyl Halides, Amines, Amides, and Other Vinyl Monomers
1. | skn-rbt 10 mg/24H open MLD | AIHAAP American Industrial Hygiene Association Journal. 23 (1962),95. | ||
2. | eye-rbt 20 mg/24H MOD | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,775. |
Reported in EPA TSCA Inventory.
Hazard Codes: T
Risk Statements: 45-10-20/21/22
R45:May cause cancer.
R10:Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 53-16-23-36/37/39-45
S53:Avoid exposure - obtain special instructions before use.
S16:Keep away from sources of ignition.
S23:Do not breathe vapour.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 3271 3/PG 3
WGK Germany: 3
RTECS: RN8770000
HazardClass: 3.2
PackingGroup: III
Experimental reproductive effects. A skin irritant. Flammable liquid when exposed to heat, sparks, or flame. To fight fire, use foam, alcohol foam, mist. When heated to decomposition it emits acrid smoke and irritating fumes.
1,2-Epoxy-4-vinylcyclohexane (CAS NO.106-86-5) is also named as 1-Vinyl-3,4-epoxycyclohexane ; 3,4-Epoxycyclohexylethylene ; 3-Vinyl-7-oxabicyclo(4.1.0)heptane ; 4-17-00-00314 (Beilstein Handbook Reference) ; 4-Vinyl-1,2-epoxycyclohexane ; 4-Vinylcyclohexane monoepoxide ; 4-Vinylcyclohexane, 1,2-epoxide ; 4-Vinylcyclohexene monoxide ; 4-Vinylcyclohexene oxide ; 4-Vinylcyclohexene-1,2-epoxide ; AI3-26045 ; BRN 0107390 ; EP-101 ; Epoxide 101 ; NSC 35409 ; Unoxat epoxide 101 ; Vinylcyclohexane monoxide ; Vinylcyclohexene monoxide .
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