Product Name

  • Name

    1,2-Epoxy-4-vinylcyclohexane

  • EINECS 203-436-1
  • CAS No. 106-86-5
  • Article Data52
  • CAS DataBase
  • Density 1.06 g/cm3
  • Solubility
  • Melting Point -100oC
  • Formula C8H12O
  • Boiling Point 169 °C at 760 mmHg
  • Molecular Weight 124.183
  • Flash Point 48.1 °C
  • Transport Information UN 3271 3/PG 3
  • Appearance Transparent Liquid
  • Safety 53-16-23-36/37/39-45
  • Risk Codes 45-10-20/21/22
  • Molecular Structure Molecular Structure of 106-86-5 (1,2-Epoxy-4-vinylcyclohexane)
  • Hazard Symbols ToxicT
  • Synonyms Epoxide 101;NSC 35409;Unoxat epoxide 101;Vinyl-3,4-epoxycyclohexane;7-Oxabicyclo[4.1.0]heptane,3-vinyl- (6CI,8CI);Cyclohexane, 1,2-epoxy-4-vinyl- (7CI);7-Oxabicyclo[4.1.0]heptane,3-ethenyl-;1-Ethenyl-3-cyclohexene oxide;1-Vinyl-3,4-epoxycyclohexane;3,4-Epoxycyclohexylethylene;3-Ethenyl-7-oxabicyclo[4.1.0]heptane;3-Vinyl-7-oxabicyclo[4.1.0]heptane;4-Vinyl-1-cyclohexene-1,2-epoxide;4-Vinylcyclohexane 1,2-epoxide;4-Vinylcyclohexane-1-oxide;4-Vinylcyclohexene monoepoxide;4-Vinylcyclohexeneoxide;Cyracure VCMX-C;
  • PSA 12.53000
  • LogP 1.73990

Synthetic route

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

Conditions
ConditionsYield
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
632-21-3

1,1,3,3-tetrachloropropanone

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

D

tetrachloroacetone hydrate
78950-58-0

tetrachloroacetone hydrate

Conditions
ConditionsYield
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
100-40-3

4-ethenylcyclohexene

A

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

B

3,4-dihydroxy-1-vinylcyclohexane
31646-64-7

3,4-dihydroxy-1-vinylcyclohexane

Conditions
ConditionsYield
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;
peracetic acid
79-21-0

peracetic acid

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

Conditions
ConditionsYield
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
100-40-3

4-ethenylcyclohexene

A

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

B

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

C

3,4-dihydroxy-1-vinylcyclohexane
31646-64-7

3,4-dihydroxy-1-vinylcyclohexane

Conditions
ConditionsYield
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
100-40-3

4-ethenylcyclohexene

A

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

B

4-Vinylcyclohex-1-en-4-ol
5537-04-2

4-Vinylcyclohex-1-en-4-ol

trans-4-Vinylcyclohex-1-en-3-ol
88301-28-4

trans-4-Vinylcyclohex-1-en-3-ol

trans-4-Vinylcyclohex-1-en-6-ol
64248-92-6, 81457-32-1, 88301-27-3

trans-4-Vinylcyclohex-1-en-6-ol

cis-4-Vinylcyclohex-1-en-6-ol
64248-92-6, 81457-32-1, 88301-27-3

cis-4-Vinylcyclohex-1-en-6-ol

cis-3-Vinylcyclohex-1-en-6-ol
88301-29-5, 88301-30-8

cis-3-Vinylcyclohex-1-en-6-ol

Conditions
ConditionsYield
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
100-40-3

4-ethenylcyclohexene

A

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

trans-3-Hydroperoxy-4-vinylcyclohex-1-en
24779-55-3

trans-3-Hydroperoxy-4-vinylcyclohex-1-en

cis-6-Hydroperoxy-3-vinylcyclohex-1-en
24779-57-5

cis-6-Hydroperoxy-3-vinylcyclohex-1-en

D

4-Hydroperoxy-4-vinylcyclohex-1-en
3736-26-3

4-Hydroperoxy-4-vinylcyclohex-1-en

trans-6-Hydroperoxy-4-vinylcyclohex-1-en
24779-56-4

trans-6-Hydroperoxy-4-vinylcyclohex-1-en

cis-6-Hydroperoxy-4-vinylcyclohex-1-en
24779-56-4

cis-6-Hydroperoxy-4-vinylcyclohex-1-en

Conditions
ConditionsYield
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
100-40-3

4-ethenylcyclohexene

acetic acid
64-19-7

acetic acid

A

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

B

3,4-dihydroxy-1-vinylcyclohexane
31646-64-7

3,4-dihydroxy-1-vinylcyclohexane

C

4-vinylcyclohexanediol-1,2 monoacetate

4-vinylcyclohexanediol-1,2 monoacetate

Conditions
ConditionsYield
With MoOBr3; dihydrogen peroxide at 70℃; for 6h; Product distribution; other cyclohexene derivatives; other molybdenum complexes;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

Conditions
ConditionsYield
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;
(+-)-4-vinyl-hexene

(+-)-4-vinyl-hexene

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

Conditions
ConditionsYield
With Perbenzoic acid; chloroform
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

B

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

Conditions
ConditionsYield
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
67-56-1

methanol

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

D

cyclohex-3-enyl acetaldehyde
24480-99-7

cyclohex-3-enyl acetaldehyde

F

2-Methoxy-5-vinyl-cyclohexanol

2-Methoxy-5-vinyl-cyclohexanol

G

C9H16O2
1243451-21-9

C9H16O2

Conditions
ConditionsYield
With dihydrogen peroxide In water at 64.84℃; for 2h; regioselective reaction;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; 2BF4(1-)*C30H32N8O3Ru(2+) In dichloromethane at 20℃; for 24h; Inert atmosphere; Darkness; regioselective reaction;
methanol
67-56-1

methanol

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

D

2-Methoxy-5-vinyl-cyclohexanol

2-Methoxy-5-vinyl-cyclohexanol

E

C9H16O2
1243451-21-9

C9H16O2

F

3-Cyclohexene-1-carboxaldehyde
100-50-5

3-Cyclohexene-1-carboxaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide In water at 65℃; for 1.5h;
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

1,1,3,3-tetramethyl-1-(2-trimethylsilanylethyl)disiloxane
154455-22-8

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
1400684-08-3

3-{2-[1,1,3,3-tetramethyl-3-(2-trimethylsilanylethyl)disiloxanyl]ethyl}-7-oxabicyclo[4.1.0]heptane

Conditions
ConditionsYield
With buffer; Karstedt's catalyst In toluene at 80 - 90℃;100%
With dihydrogen hexachloroplatinate at 75 - 85℃; for 2h;
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

Triethoxysilane
998-30-1

Triethoxysilane

(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)triethoxysilane
10217-34-2

(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)triethoxysilane

Conditions
ConditionsYield
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%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

1,1,1,3,5,5,5-heptamethyltrisiloxan
1873-88-7

1,1,1,3,5,5,5-heptamethyltrisiloxan

3-(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)-1,1,1,3,5,5,5-heptamethyltrisiloxane

3-(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)-1,1,1,3,5,5,5-heptamethyltrisiloxane

Conditions
ConditionsYield
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
106-86-5

1,2-Epoxy-4-vinylcyclohexane

poly(methylhydrosiloxane)

poly(methylhydrosiloxane)

poly[methyl(4-ethylcyclohexyl-1,2-epoxide)]siloxane

poly[methyl(4-ethylcyclohexyl-1,2-epoxide)]siloxane

Conditions
ConditionsYield
With platinum In benzene at 20℃; for 34h;98%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

1,1,3,3-Tetramethyldisiloxane
3277-26-7

1,1,3,3-Tetramethyldisiloxane

C12H26O2Si2

C12H26O2Si2

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer In neat (no solvent) at 50℃; for 2h;98%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

1,1,3,3-Tetramethyldisiloxane
3277-26-7

1,1,3,3-Tetramethyldisiloxane

1,3-bis(2(3,4-epoxycyclohexyl)ethyl)-1,1,3,3-tetramethyldisiloxane
18724-32-8

1,3-bis(2(3,4-epoxycyclohexyl)ethyl)-1,1,3,3-tetramethyldisiloxane

Conditions
ConditionsYield
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
106-86-5

1,2-Epoxy-4-vinylcyclohexane

1,1,3,3,5,5,7,7-octamethyltetrasiloxane
1000-05-1

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
151110-81-5

(1,7-bis(1,2-epoxycyclohexyl-4-ethyl))-1,1,3,3,5,5,7,7-octamethyltetrasiloxane

Conditions
ConditionsYield
polymer-bound Wilkinson's catalyst In toluene at 100 - 115℃; for 48h; Heating / reflux;96%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

3,4-dihydroxy-1-vinylcyclohexane
31646-64-7

3,4-dihydroxy-1-vinylcyclohexane

Conditions
ConditionsYield
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
106-86-5

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
881829-77-2

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

1-[2-(3,4-epoxycyclohexyl)ethyl]dimethylsiloxy-3,5,7,9,11,13,15-heptakis(trimethylsiloxy)-pentacyclo[9.5.1.1(3,9).1(5,15).1(7,13)]octasiloxane

1-[2-(3,4-epoxycyclohexyl)ethyl]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
ConditionsYield
1,3-di(η2-vinyl)-1.1.3.3-tetramethyldisiloxane platinum(0) In toluene at 20℃; for 2h;95%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C26H68OSi7

C26H68OSi7

C50H104O4Si7

C50H104O4Si7

Conditions
ConditionsYield
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
106-86-5

1,2-Epoxy-4-vinylcyclohexane

ethylcyclohexene oxide

ethylcyclohexene oxide

Conditions
ConditionsYield
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
106-86-5

1,2-Epoxy-4-vinylcyclohexane

dimethylmethoxysilane
18033-75-5

dimethylmethoxysilane

(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)dimethylsilane

(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)dimethylsilane

Conditions
ConditionsYield
With C24H30ClN3NiO2; sodium t-butanolate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; Glovebox;93%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

4-vinylcyclohex-1-ene sulfide

4-vinylcyclohex-1-ene sulfide

Conditions
ConditionsYield
With aluminum oxide; thiourea In water at 25℃; for 2h; Inert atmosphere;93%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

para-tert-butylphenol
98-54-4

para-tert-butylphenol

C18H26O2

C18H26O2

Conditions
ConditionsYield
With potassium hydroxide In toluene at 20 - 105℃; for 18h; Reagent/catalyst; Temperature; Solvent;93%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

1-dimethylosiloxy-3,5,7,9,11,13,15-heptacyclohexylpentacyclo[9.5.113,9.15,15.17,13]octasiloxane

1-dimethylosiloxy-3,5,7,9,11,13,15-heptacyclohexylpentacyclo[9.5.113,9.15,15.17,13]octasiloxane

C38H82O14Si9

C38H82O14Si9

Conditions
ConditionsYield
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%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

HSiPh3
789-25-3

HSiPh3

C26H28OSi

C26H28OSi

Conditions
ConditionsYield
With C77H70N2OPtSi2 In toluene at 80℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction;91%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

3-methacryloxypropyltrichlorosilane

3-methacryloxypropyltrichlorosilane

trimethoxysilane
2487-90-3

trimethoxysilane

trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane
3388-04-3

trimethoxy[2-(7-oxabicyclo[4.1.0]-hept-3-yl)ethyl]silane

Conditions
ConditionsYield
chloroplatinic acid90%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

carbon dioxide
124-38-9

carbon dioxide

5-vinylhexahydrobenzo[d][1,3]dioxol-2-one

5-vinylhexahydrobenzo[d][1,3]dioxol-2-one

Conditions
ConditionsYield
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%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

carbon dioxide
124-38-9

carbon dioxide

cis-5-vinylhexahydrobenzo[d][1,3]dioxol-2-one

cis-5-vinylhexahydrobenzo[d][1,3]dioxol-2-one

Conditions
ConditionsYield
With C20H13FeN2O5; tetrabutylammomium bromide at 100℃; under 3750.38 - 7500.75 Torr; for 18h; Sealed tube;90%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

4-allylguaiacol
97-53-0

4-allylguaiacol

octakis(dimethylsiloxy)octasilsesquioxane

octakis(dimethylsiloxy)octasilsesquioxane

C88H152O32Si16

C88H152O32Si16

Conditions
ConditionsYield
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%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

diphenylsilane
775-12-2

diphenylsilane

2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyldiphenylsilane

2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyldiphenylsilane

Conditions
ConditionsYield
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%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

Triethoxyvinylsilane
78-08-0

Triethoxyvinylsilane

octakis(dimethylsiloxy)octasilsesquioxane

octakis(dimethylsiloxy)octasilsesquioxane

C80H176O36Si20

C80H176O36Si20

Conditions
ConditionsYield
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%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

Methyl 10-undecenoate
111-81-9

Methyl 10-undecenoate

octakis(dimethylsiloxy)octasilsesquioxane

octakis(dimethylsiloxy)octasilsesquioxane

C96H192O32Si16

C96H192O32Si16

Conditions
ConditionsYield
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%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

phenylsilane
694-53-1

phenylsilane

(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)(phenyl)silane

(2-(7-oxabicyclo[4.1.0]heptan-3-yl)ethyl)(phenyl)silane

Conditions
ConditionsYield
With nickel(II) chloride hexahydrate; potassium tert-butylate In tetrahydrofuran at -30℃; for 1h; Schlenk technique; Inert atmosphere; Sealed tube;87%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

iodobenzene
591-50-4

iodobenzene

C14H18O

C14H18O

Conditions
ConditionsYield
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%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

carbon dioxide
124-38-9

carbon dioxide

cis-5-vinylhexahydrobenzo[d][1,3]dioxol-2-one

cis-5-vinylhexahydrobenzo[d][1,3]dioxol-2-one

Conditions
ConditionsYield
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;
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

octakis(dimethylsiloxy)octasilsesquioxane

octakis(dimethylsiloxy)octasilsesquioxane

C88H176O28Si16

C88H176O28Si16

Conditions
ConditionsYield
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
106-86-5

1,2-Epoxy-4-vinylcyclohexane

4-vinyl cyclohexene dioxide

4-vinyl cyclohexene dioxide

Conditions
ConditionsYield
With oxygen; copper(II) bis(trifluoromethanesulfonate); dimethyl sulfoxide; bismuth at 100℃; for 1.3h;77%
1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

Dimethylphenylsilane
766-77-8

Dimethylphenylsilane

<2-(3,4-Epoxy-cyclohexyl)-aethyl>-dimethyl-phenyl-silan
20988-14-1

<2-(3,4-Epoxy-cyclohexyl)-aethyl>-dimethyl-phenyl-silan

Conditions
ConditionsYield
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.

1,2-Epoxy-4-vinylcyclohexane Chemical Properties

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: C8H12
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

1,2-Epoxy-4-vinylcyclohexane Toxicity Data With Reference

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.

1,2-Epoxy-4-vinylcyclohexane Consensus Reports

Reported in EPA TSCA Inventory.

1,2-Epoxy-4-vinylcyclohexane Safety Profile

Hazard Codes: ToxicT
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 Specification

 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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