Product Name

  • Name

    VINYLCYCLOHEXANE

  • EINECS 211-779-3
  • CAS No. 695-12-5
  • Article Data113
  • CAS DataBase
  • Density 0.865 g/cm3
  • Solubility Insoluble in water.
  • Melting Point 121 °C
  • Formula C8H14
  • Boiling Point 126.9 °C at 760 mmHg
  • Molecular Weight 110.199
  • Flash Point 21.1 °C
  • Transport Information UN 3295 3/PG 2
  • Appearance clear colourless liquid
  • Safety 16
  • Risk Codes 10
  • Molecular Structure Molecular Structure of 695-12-5 (VINYLCYCLOHEXANE)
  • Hazard Symbols R11:Highly flammable.;
  • Synonyms Cyclohexane,vinyl- (6CI,8CI);Cyclohexylethene;Cyclohexylethylene;Ethenylcyclohexane;NSC73939;Vinylcyclohexane;
  • PSA 0.00000
  • LogP 2.75270

Synthetic route

1-<2-trimethylsilyl)ethyl>cyclohexanol
81372-29-4

1-<2-trimethylsilyl)ethyl>cyclohexanol

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With borontrifluoride acetic acid In dichloromethane at 25℃; for 0.0833333h;95%
2-cyclohexylacetylene
931-48-6

2-cyclohexylacetylene

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With hydrogen In hexane at 20℃; under 760.051 Torr; for 14h;92%
With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; C19H13I2N3O2Ru; hydrogen In isopropyl alcohol at 80℃; under 3750.38 Torr; for 1h; Autoclave; Schlenk technique; chemoselective reaction;89%
With hydrogen In toluene at 20℃; under 38002.6 Torr; for 12h; Autoclave; chemoselective reaction;72%
(lithiomethyl)dimesitylborane

(lithiomethyl)dimesitylborane

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With trifluoroacetic anhydride76%
Methylenetriphenylphosphorane
19493-09-5

Methylenetriphenylphosphorane

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
In tetrahydrofuran 1) 2 h, reflux, 2) 12 h, r.t.;A 68%
B n/a
C10H15O2P

C10H15O2P

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
In 1,4-dioxane at 120℃; for 15h; Schlenk technique; Inert atmosphere;65%
methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In acetonitrile Wittig Olefination; Inert atmosphere; Glovebox; Electrochemical reaction;57%
acetophenone
98-86-2

acetophenone

A

styrene
292638-84-7

styrene

B

vinylcyclohexane
695-12-5

vinylcyclohexane

C

ethylbenzene
100-41-4

ethylbenzene

Conditions
ConditionsYield
With sodium tetrahydroborate; hydrogen; nickel dichloride In isopropyl alcohol at 60 - 70℃; for 12h;A 56%
B 14%
C 28%
vinylidenecyclohexane
5664-20-0

vinylidenecyclohexane

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

ethylidenecyclohexane
1003-64-1

ethylidenecyclohexane

Conditions
ConditionsYield
Stage #1: vinylidenecyclohexane With triethylsilane; indium(III) chloride; triethyl borane In hexane; acetonitrile at 20℃; for 2h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In hexane; acetonitrile regioselective reaction;
A 10%
B 32%
With water; diisobutylaluminium hydride 1.) hexane, 15 h, 25°C; 2.) 0°C; Multistep reaction;
cyclohexylmercury chloride
24371-94-6

cyclohexylmercury chloride

tri-n-butyl(vinyl)tin
7486-35-3

tri-n-butyl(vinyl)tin

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
In dimethyl sulfoxide Irradiation (UV/VIS); mixt. of substrate and mercurial is irradiated in nitrogen-purged solvent in Pyrex tube with 350-nm Rayonet photoreactor for 24 h; mixt. is poured into water, extd., extract is washed twice with aq. sodium thiosulfate, dried over anhyd. Na2SO4, concd.; (1)H-NMR;8%
styrene
292638-84-7

styrene

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

ethyl-cyclohexane
1678-91-7

ethyl-cyclohexane

C

ethylbenzene
100-41-4

ethylbenzene

Conditions
ConditionsYield
With hydrogen; (η3-C3H5)Co[P(OMe)3]3 for 20.5h; Ambient temperature;A 2.8%
B 0.3%
C 1.5%
cyclohexyl ethyl acetate
21722-83-8

cyclohexyl ethyl acetate

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
at 480℃;
1-cyclohexylethan-1-yl acetate
13487-27-9

1-cyclohexylethan-1-yl acetate

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

ethylidenecyclohexane
1003-64-1

ethylidenecyclohexane

Conditions
ConditionsYield
at 450℃;
(2-iodoethyl)cyclohexane
80203-35-6

(2-iodoethyl)cyclohexane

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With quinoline
dithiocarbonic acid O-(1-cyclohexyl-ethyl ester)-S-methyl ester
99977-91-0

dithiocarbonic acid O-(1-cyclohexyl-ethyl ester)-S-methyl ester

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

ethylidenecyclohexane
1003-64-1

ethylidenecyclohexane

Conditions
ConditionsYield
at 250℃;
Cyclohexyloxirane
3483-39-4

Cyclohexyloxirane

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

rac-1-cyclohexylethanol
1193-81-3

rac-1-cyclohexylethanol

Conditions
ConditionsYield
With 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium 1) THF, -78 deg C, 5 min 2) MeOH, -78 deg C; Multistep reaction;
vinyl acetate
108-05-4

vinyl acetate

cyclohexane
110-82-7

cyclohexane

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
19 % Chromat.
2-cyclohexylacetylene
931-48-6

2-cyclohexylacetylene

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

octane
111-65-9

octane

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; 18-crown-6 ether; dihydrogen peroxide; sodium methylate 1.) THF, 65 deg C, 3 h, 2.) CH3OH, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;
ethyl-cyclohexane
1678-91-7

ethyl-cyclohexane

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

1-ethylcyclohexene
1453-24-3

1-ethylcyclohexene

C

ethylidenecyclohexane
1003-64-1

ethylidenecyclohexane

D

4-ethylcyclohexene
3742-42-5, 75382-76-2

4-ethylcyclohexene

E

3-ethyl-1-cyclohexene
2808-71-1

3-ethyl-1-cyclohexene

Conditions
ConditionsYield
trans-carbonylchlorobis(trimethylphosphine)rhodium under 50 Torr; for 72h; Mechanism; Irradiation;
(E)-cyclooctene
931-89-5

(E)-cyclooctene

A

(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

B

vinylcyclohexane
695-12-5

vinylcyclohexane

C

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
at 512℃; Rate constant; further temperatures;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With η5-C9H11Fe(CO)2(isobutylene)+BF-; hydrogen; sodium iodide; palladium on activated charcoal Multistep reaction;
Di-(cyclohexyl)-n-butylboran
6917-84-6

Di-(cyclohexyl)-n-butylboran

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

A

1-hexene
592-41-6

1-hexene

B

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With iodine Product distribution; 1.) THF, room temperature, 1 h, 2.) THF, -78 deg C; other trialkylboranes;
2-chloro-1-cyclohexyl-1-ethanone
1892-09-7

2-chloro-1-cyclohexyl-1-ethanone

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With lithium aluminium tetrahydride; aluminium trichloride; lithium 1.) Et2O, 2.) THF; Yield given. Multistep reaction;
2-cyclohexylpropanoic acid
6051-13-4

2-cyclohexylpropanoic acid

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

ethylidenecyclohexane
1003-64-1

ethylidenecyclohexane

Conditions
ConditionsYield
With pyridine; lead(IV) acetate; copper diacetate In benzene for 4h; Heating;
cyclohexyl ethyl acetate
21722-83-8

cyclohexyl ethyl acetate

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
at 400℃; Kinetics; Thermodynamic data; var. temp., pressure; ΔH(excit.);
rac-1-cyclohexylethanol
1193-81-3

rac-1-cyclohexylethanol

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

ethylidenecyclohexane
1003-64-1

ethylidenecyclohexane

Conditions
ConditionsYield
With dimethyl sulfoxide at 175℃; for 24h; Yield given. Yields of byproduct given;
5 % ruthenium on Al2O3; zirconium(IV) oxide at 376 - 398℃; Product distribution / selectivity;
trans,trans-4'-butyl<1,1'-bicyclohexyl>-4-carbonitrile
70784-10-0

trans,trans-4'-butyl<1,1'-bicyclohexyl>-4-carbonitrile

C16H20(2)H2O

C16H20(2)H2O

A

vinylcyclohexane
695-12-5

vinylcyclohexane

(1R,2R)-2-Cyclohexyl-1-phenyl-cyclobutanol

(1R,2R)-2-Cyclohexyl-1-phenyl-cyclobutanol

(1R,2S)-2-Cyclohexyl-1-phenyl-cyclobutanol

(1R,2S)-2-Cyclohexyl-1-phenyl-cyclobutanol

D

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
at 30℃; Product distribution; Irradiation; Norrish II photoreactivity; different solvents, different temperatures;
(2-cyclohexylidene-ethyl)dimethyl(phenyl)silane
79753-67-6

(2-cyclohexylidene-ethyl)dimethyl(phenyl)silane

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With trifluoroacetic acid In tetrachloromethane for 20h; Ambient temperature;95 % Spectr.
bicyclo<5.1.0>octan-2-one tosylhydrazone
73733-09-2

bicyclo<5.1.0>octan-2-one tosylhydrazone

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

1-octen-7-yne
65909-92-4

1-octen-7-yne

C

bicyclo<4.2.0>oct-6-ene
37680-26-5

bicyclo<4.2.0>oct-6-ene

Conditions
ConditionsYield
With sodium methylate at 160 - 170℃; under 0.5 Torr;A 10 % Chromat.
B 65 % Chromat.
C 25 % Chromat.
With sodium methylate at 160 - 170℃; under 0.5 Torr; Mechanism; Product distribution;A 10 % Chromat.
B 65 % Chromat.
C 25 % Chromat.
exo-7-chloromethylbicyclo<4.1.0>heptane
76200-08-3

exo-7-chloromethylbicyclo<4.1.0>heptane

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

exo-7-methylbicyclo<4.1.0>heptane
14135-43-4

exo-7-methylbicyclo<4.1.0>heptane

Conditions
ConditionsYield
With triphenylstannane In pentane at 25℃; for 24h; Irradiation; Yield given. Yields of byproduct given;
With triphenylstannane In pentane at 25℃; for 24h; Product distribution; Rate constant; Mechanism; Irradiation; several amount of reagent;
1-chloro-2-vinylcyclohexane

1-chloro-2-vinylcyclohexane

vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With triphenylstannane for 24h; Irradiation;
vinylcyclohexane
695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With 4-methylmorpholine N-oxide In water; acetone at 20℃; for 3.5h; Inert atmosphere;100%
Stage #1: vinylcyclohexane With sodium periodate; acetic acid; lithium bromide at 95℃; for 18h; Prevost-Woodward reaction;
Stage #2: With potassium carbonate In methanol at 25℃; for 24h;
85%
With osmium(VIII) oxide; N-methyl-2-indolinone In water; acetone; acetonitrile Ambient temperature;83%
vinylcyclohexane
695-12-5

vinylcyclohexane

C8H14O

C8H14O

Conditions
ConditionsYield
With titanium(IV) isopropylate; Pentafluorobenzoic acid; C32H22F10N2O2; dihydrogen peroxide In water; 1,2-dichloro-ethane at 20℃; for 45h; Inert atmosphere; enantioselective reaction;100%
vinylcyclohexane
695-12-5

vinylcyclohexane

Cyclohexyloxirane
3483-39-4

Cyclohexyloxirane

Conditions
ConditionsYield
With peracetic acid; C80H84Mn2N8O4*4ClO4(1-) In acetonitrile at 0℃; for 0.5h;99%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 18h;97%
With bis-trimethylsilanyl peroxide; rhenium(VII) oxide In dichloromethane for 7h;95%
vinylcyclohexane
695-12-5

vinylcyclohexane

benzoic acid
65-85-0

benzoic acid

2-bromo-2-cyclohexylethyl benzoate
1403879-55-9

2-bromo-2-cyclohexylethyl benzoate

Conditions
ConditionsYield
With N-bromophthalimide; 4-methylmorpholine N-oxide; sodium sulfate In dichloromethane at 20℃; for 22h; diastereoselective reaction;99%
With N-Bromosuccinimide; 5,6-difluoro-2-(1-phenylethyl)benzo[d][1,2]selenazol-3(2H)-one In dichloromethane at 20℃; for 10h;68%
vinylcyclohexane
695-12-5

vinylcyclohexane

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethyl (2-cyclohexylethyl)phosphonate

dimethyl (2-cyclohexylethyl)phosphonate

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In neat (no solvent) for 0.5h; Solvent; UV-irradiation;99%
vinylcyclohexane
695-12-5

vinylcyclohexane

ethylidenecyclohexane
1003-64-1

ethylidenecyclohexane

Conditions
ConditionsYield
bis(cyclopentadienyl)titanium dichloride; lithium aluminium tetrahydride at 180℃; for 2h;98%
With sodium azide on γ-alumina at 20℃;
With [(dppb)Pt(C6F5)(H2O)]OTf In chloroform at 50℃; for 24h;97 %Chromat.
vinylcyclohexane
695-12-5

vinylcyclohexane

1-(5,6-Dihydro-4H-pyran-2-yl)-2,2-dimethyl-propan-1-one

1-(5,6-Dihydro-4H-pyran-2-yl)-2,2-dimethyl-propan-1-one

1-[3-(2-Cyclohexyl-ethyl)-5,6-dihydro-4H-pyran-2-yl]-2,2-dimethyl-propan-1-one

1-[3-(2-Cyclohexyl-ethyl)-5,6-dihydro-4H-pyran-2-yl]-2,2-dimethyl-propan-1-one

Conditions
ConditionsYield
With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 135℃; for 12h;98%
vinylcyclohexane
695-12-5

vinylcyclohexane

phenylphosphinic acid
1779-48-2

phenylphosphinic acid

(2-cyclohexylethyl)(phenyl)phosphinic acid

(2-cyclohexylethyl)(phenyl)phosphinic acid

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In water for 2h; Solvent; UV-irradiation; Green chemistry;98%
vinylcyclohexane
695-12-5

vinylcyclohexane

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

((2-cyclohexylethyl)sulfonyl)benzene
126002-58-2

((2-cyclohexylethyl)sulfonyl)benzene

Conditions
ConditionsYield
With [Ir(dF(CF3)ppy)2(dtbbpy)]PF6; water; acetic acid In dichloromethane at 20℃; for 10h; Inert atmosphere; Irradiation; regioselective reaction;98%
vinylcyclohexane
695-12-5

vinylcyclohexane

(E)-1-phenyl-N-(1-phenylethylidene)methanamine
14428-98-9, 98325-59-8, 98359-08-1

(E)-1-phenyl-N-(1-phenylethylidene)methanamine

1-[2-(2-cyclohexyl-ethyl)-phenyl]-ethanone

1-[2-(2-cyclohexyl-ethyl)-phenyl]-ethanone

Conditions
ConditionsYield
Stage #1: vinylcyclohexane; (E)-1-phenyl-N-(1-phenylethylidene)methanamine With [RhCl(Ph3P)2] for 0.25h; microwave irradiation;
Stage #2: Acid hydrolysis;
97%
vinylcyclohexane
695-12-5

vinylcyclohexane

4-methoxy-phenol
150-76-5

4-methoxy-phenol

4-methoxy-2-(1-cyclohexylethyl)phenol
1173929-13-9

4-methoxy-2-(1-cyclohexylethyl)phenol

Conditions
ConditionsYield
With decacarbonyldirhenium(0) In toluene at 150℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;97%
vinylcyclohexane
695-12-5

vinylcyclohexane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-cyclohexyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethane

2-cyclohexyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethane

Conditions
ConditionsYield
With (iPrPNN)CoCl2; sodium triethylborohydride In tetrahydrofuran; toluene at 25℃; for 0.25h; Inert atmosphere; Glovebox; Schlenk technique; chemoselective reaction;97%
Stage #1: vinylcyclohexane; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With 6-di-tert-butylphosphinomethyl-2,2'-bipyridine In tetrahydrofuran for 0.0166667h; Inert atmosphere; Glovebox; Schlenk technique;
Stage #2: With sodium triethylborohydride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; Glovebox; Schlenk technique;
93%
With silver hexafluoroantimonate at 60℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere;92%
vinylcyclohexane
695-12-5

vinylcyclohexane

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

(2-cyclohexylethyl)diphenylphosphine oxide

(2-cyclohexylethyl)diphenylphosphine oxide

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In N,N-dimethyl-formamide for 2h; Solvent; UV-irradiation; Green chemistry;97%
vinylcyclohexane
695-12-5

vinylcyclohexane

ethyl 2,2-difluoro-2-iodoacetate
7648-30-8

ethyl 2,2-difluoro-2-iodoacetate

ethyl 4-cyclohexyl-2,2-difluoro-4-iodobutanoate

ethyl 4-cyclohexyl-2,2-difluoro-4-iodobutanoate

Conditions
ConditionsYield
With diethylzinc In hexane; acetonitrile at -20℃; for 16h; Schlenk technique; Inert atmosphere;97%
With potassium carbonate In acetone at 20℃; for 16h; Schlenk technique; Inert atmosphere; Irradiation; Green chemistry;96%
With potassium carbonate In acetone at 20℃; for 16h; Irradiation;96%
vinylcyclohexane
695-12-5

vinylcyclohexane

iodotrifluoromethane
2314-97-8

iodotrifluoromethane

C9H13F3

C9H13F3

Conditions
ConditionsYield
With (dppf)Ni(o-tol)Cl; sodium t-butanolate In Hexafluorobenzene at 50℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;97%
vinylcyclohexane
695-12-5

vinylcyclohexane

(R)-1-cyclohexylethane-1,2-diol
59411-58-4, 61414-09-3, 125874-67-1, 87858-06-8

(R)-1-cyclohexylethane-1,2-diol

Conditions
ConditionsYield
With methanesulfonamide; AD-mix β; water In ethanol at 4℃; for 24h; Sharpless Dihydroxylation;96%
Stage #1: vinylcyclohexane With 2,2'-bis(1,3,2-benzodioxaborole); (bicyclo[2.2.1]hepta-2,5-diene)-(2,4-pentanedionato)rhodium (I); (S)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline In tetrahydrofuran at 20℃; for 6h;
Stage #2: With sodium hydroxide; dihydrogen peroxide Product distribution / selectivity;
81%
Stage #1: vinylcyclohexane With 1,8-diazabicyclo[5.4.0]undec-7-ene; (2R,3S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4-diol; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; Sealed tube;
Stage #2: With water; dihydrogen peroxide; sodium hydroxide at 0 - 20℃; for 4h; Inert atmosphere; Sealed tube; enantioselective reaction;
68%
vinylcyclohexane
695-12-5

vinylcyclohexane

2-pyridylmethyl formate
401515-97-7

2-pyridylmethyl formate

pyridin-2-ylmethyl 3-cyclohexylpropanoate

pyridin-2-ylmethyl 3-cyclohexylpropanoate

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; dodecacarbonyl-triangulo-triruthenium In N,N-dimethyl-formamide at 70℃; for 12h;96%
With dodecacarbonyl-triangulo-triruthenium In N,N-dimethyl-formamide at 135℃; for 12h;87%
With 1,3-bis(1-adamantyl)benzimidazoliumchloride, 1,3-dicyclohexylbenzimidazolium chloride; ruthenium(II) (norbanadiene)Cl2; potassium tert-butylate In tetrahydrofuran at 90℃; for 12h; Reagent/catalyst; Concentration; regioselective reaction;87%
vinylcyclohexane
695-12-5

vinylcyclohexane

Trichloroacetyl chloride
76-02-8

Trichloroacetyl chloride

2,2-dichloro-3-(cyclohexyl)cyclobutanone
1029080-53-2

2,2-dichloro-3-(cyclohexyl)cyclobutanone

Conditions
ConditionsYield
With copper; zinc; trichlorophosphate In diethyl ether at 40℃; for 2h;96%
With zinc/copper couple; trichlorophosphate In diethyl ether Reflux;
vinylcyclohexane
695-12-5

vinylcyclohexane

6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione
1104636-73-8

6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione

2-(2-cyclohexylvinyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

2-(2-cyclohexylvinyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 24h; Inert atmosphere; stereoselective reaction;96%
vinylcyclohexane
695-12-5

vinylcyclohexane

2,2-dimethyl-3,4-dihydro-2H-naphthalen-1-one
2977-45-9

2,2-dimethyl-3,4-dihydro-2H-naphthalen-1-one

C20H28O

C20H28O

Conditions
ConditionsYield
With Fe(PMe3)4 at 70℃; for 20h; Inert atmosphere; regioselective reaction;96%
vinylcyclohexane
695-12-5

vinylcyclohexane

[1-chloro-2-(pentafluoro-λ6-sulfanyl)ethyl]cyclohexane
1263301-67-2

[1-chloro-2-(pentafluoro-λ6-sulfanyl)ethyl]cyclohexane

Conditions
ConditionsYield
Stage #1: vinylcyclohexane With pentafluorosulfanyl chloride In dichloromethane at -40℃;
Stage #2: With triethyl borane In hexane; dichloromethane at -40 - 20℃;
Stage #3: With water; sodium hydrogencarbonate In hexane; dichloromethane
95%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

vinylcyclohexane
695-12-5

vinylcyclohexane

3,3'-bis(2-cyclohexylethyl)-2,2'-bipyridine
1402856-01-2

3,3'-bis(2-cyclohexylethyl)-2,2'-bipyridine

Conditions
ConditionsYield
With rhodium(III) acetylacetonate; 1,3-bis(mesityl)imidazolium chloride; sodium t-butanolate In toluene at 130℃; for 2h; regioselective reaction;95%
vinylcyclohexane
695-12-5

vinylcyclohexane

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

(3,3,4,4,5,5,6,6,6-nonafluoro-1-iodohexyl)cyclohexane
1464148-71-7

(3,3,4,4,5,5,6,6,6-nonafluoro-1-iodohexyl)cyclohexane

Conditions
ConditionsYield
With tri-tert-butyl phosphine; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 12h; regioselective reaction;95%
With sodium dithionite; C8ClF16O4S(1-)*C8H20N(1+); sodium hydrogencarbonate In water at 20℃; for 12h;90%
With tri-tert-butyl phosphine In dichloromethane at 30℃; for 1h; Inert atmosphere; Irradiation; Sealed tube;87%
With potassium carbonate In acetone at 20℃; for 16h; Schlenk technique; Inert atmosphere; Irradiation; Green chemistry;79%
With tri-tert-butyl phosphine; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;
vinylcyclohexane
695-12-5

vinylcyclohexane

diphenylsilane
775-12-2

diphenylsilane

(2-cyclohexylethyl)diphenylsilane

(2-cyclohexylethyl)diphenylsilane

Conditions
ConditionsYield
With sodium methylate In tetrahydrofuran Heating;95%
With [(2-Ph2PC6H4)2PhSiCo(H)(Cl)(PMe3)] In neat (no solvent) at 70℃; for 30h; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere; regioselective reaction;95%
With (1,3-diadamantylimidazol-2-ylidene)(PPh3)CoCl In toluene at 70℃; for 30h;89%
vinylcyclohexane
695-12-5

vinylcyclohexane

1,2-dibromo-1-cyclohexylethane
81602-60-0

1,2-dibromo-1-cyclohexylethane

Conditions
ConditionsYield
With bromine In chloroform at 0 - 20℃; for 1h; Inert atmosphere;94%
With bromine
With bromine In tetrachloromethane
With bromine In dichloromethane at 0 - 5℃;
With urea hydrogen peroxide adduct; trifluoroacetic acid; lithium bromide at 100℃; for 1h;
vinylcyclohexane
695-12-5

vinylcyclohexane

o-iodoacetanilide
19591-17-4

o-iodoacetanilide

1-(3-cyclohexylindolin-1-yl)ethan-1-one

1-(3-cyclohexylindolin-1-yl)ethan-1-one

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; triethylamine; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In acetone at 35℃; for 48h; Heck Reaction; Inert atmosphere; Irradiation;94%
vinylcyclohexane
695-12-5

vinylcyclohexane

2,3-dihydro-1H-benzo[b]silole

2,3-dihydro-1H-benzo[b]silole

(S)-1-(2-cyclohexylethyl)-2,3-dihydro-1H-benzo[b]silole

(S)-1-(2-cyclohexylethyl)-2,3-dihydro-1H-benzo[b]silole

Conditions
ConditionsYield
With C47H47N2O2Sc In benzene-d6 at 75℃; Schlenk technique; Sealed tube; enantioselective reaction;94%
vinylcyclohexane
695-12-5

vinylcyclohexane

N-(2-methylbenzoyl)-8-aminoquinoline
1182669-71-1

N-(2-methylbenzoyl)-8-aminoquinoline

2-(2-cyclohexylethyl)-6-methyl-N-(quinolin-8-yl)benzamide

2-(2-cyclohexylethyl)-6-methyl-N-(quinolin-8-yl)benzamide

Conditions
ConditionsYield
With ortho-methylbenzoic acid; di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) In toluene at 160℃; for 12h; Sealed tube;94%
vinylcyclohexane
695-12-5

vinylcyclohexane

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-cyano-4-cyclohexyl-butyric acid ethyl ester

2-cyano-4-cyclohexyl-butyric acid ethyl ester

Conditions
ConditionsYield
With pyridine; Eosin Y; 1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate at 23℃; for 14h; Inert atmosphere; Sealed tube; Irradiation;93%
With dibenzoyl peroxide (heating);

Vinylcyclohexane Specification

The CAS register number of Vinylcyclohexane is 695-12-5. It also can be called as Cyclohexane, vinyl- and the IUPAC name about this chemical is ethenylcyclohexane. The molecular formula about this chemical is C8H14 and the molecular weight is 110.20. Classification code about this chemical is Reproductive Effect. This chemical is flammable. When you are using it, please keep away from sources of ignition.

Physical properties about Vinylcyclohexane are: (1)ACD/LogP: 3.90; (2)ACD/LogD (pH 5.5): 3.9; (3)ACD/LogD (pH 7.4): 3.9; (4)ACD/BCF (pH 5.5): 541.15; (5)ACD/BCF (pH 7.4): 541.15; (6)ACD/KOC (pH 5.5): 3148.54; (7)ACD/KOC (pH 7.4): 3148.54 ; (8)#Freely Rotating Bonds: 1; (9)Index of Refraction: 1.515; (10)Molar Refractivity: 38.45 cm3; (11)Molar Volume: 127.3 cm3; (12)Polarizability: 15.24x10-24cm3; (13)Surface Tension: 28.8 dyne/cm; (14)Flash Point: 21.1 °C; (15)Enthalpy of Vaporization: 34.96 kJ/mol; (16)Boiling Point: 126.9 °C at 760 mmHg; (17)Vapour Pressure: 13.8 mmHg at 25°C.

Preparation: this chemical can be prepared by 1-(2-trimethylsilanyl-ethyl)-cyclohexanol. This reaction will need reagent BF3*AcOH and solvent CH2Cl2. The reaction time is 5 min with reaction temperature of 25 °C. The yield is about 95%.

Uses of Vinylcyclohexane: it can be used to produce 1-cyclohexyl-ethanone at temperature of 60 ℃. This reaction will need reagent PdCl(NO2)(CH3CN)2 and solvent benzene.

You can still convert the following datas into molecular structure:
(1)SMILES: C=C\C1CCCCC1
(2)InChI: InChI=1/C8H14/c1-2-8-6-4-3-5-7-8/h2,8H,1,3-7H2
(3)InChIKey: LDLDYFCCDKENPD-UHFFFAOYAK
(4)Std. InChI: InChI=1S/C8H14/c1-2-8-6-4-3-5-7-8/h2,8H,1,3-7H2
(5)Std. InChIKey: LDLDYFCCDKENPD-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 27gm/m3/2H (27000mg/m3)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 22, 1986.
mouse LDLo oral 4gm/kg (4000mg/kg) LIVER: FATTY LIVER DEGERATION

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 30(7), Pg. 28, 1965.
rat LC50 inhalation 20500mg/m3 (20500mg/m3) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 30(7), Pg. 28, 1965.
rat LDLo oral 4gm/kg (4000mg/kg) LIVER: FATTY LIVER DEGERATION

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 30(7), Pg. 28, 1965.

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