695-12-5

Basic information

• Product Name: VINYLCYCLOHEXANE
• Synonyms: VINYLCYCLOHEXANE;1-Vinylcyclohexane;Cyclohexane, vinyl-;cyclohexane,ethenyl-;Cyclohexane,ethenyl-(9CI);Cyclohexane,vinyl-;Cyclohexylethene;ethenyl-cyclohexan
• CAS NO: 695-12-5
• Molecular Formula: C₈H₁₄
• Molecular Weight: 110.2
• EINECS: 211-779-3
• Mol File: 695-12-5.mol
• Article Data: 69

Chemical Properties

• Melting Point: 121 °C
• Boiling Point: 128 °C(lit.)
• Flash Point: 70 °F
• Appearance: clear colourless liquid
• Density: 0.805 g/mL at 25 °C(lit.)
• Vapor Pressure: 13.8mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility: Insoluble in water.
• Stability: Light Sensitive
• BRN: 1304663
• CAS DataBase Reference: VINYLCYCLOHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: VINYLCYCLOHEXANE(695-12-5)
• EPA Substance Registry System: VINYLCYCLOHEXANE(695-12-5)

Safety Data

• Hazard Codes: F:Highly flammable
• Statements: 10
• Safety Statements: 16
• RIDADR: UN 3295 3/PG 2
• WGK Germany: 3
• RTECS: GV7800000
• F: 10
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 695-12-5(Hazardous Substances Data)

Usage

Description

VINYLCYCLOHEXANE is a clear, colorless liquid that serves as a versatile reagent in various chemical reactions and processes.

Uses

Used in Chemical Synthesis:
VINYLCYCLOHEXANE is used as a reagent in cationic nickel(II)-catalyzed hydrosilylation of alkenes for facilitating the formation of new chemical bonds and creating a wide range of products.
Used in Pharmaceutical Industry:
VINYLCYCLOHEXANE is used as a starting material or intermediate in the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and therapies.
Used in Polymer Industry:
VINYLCYCLOHEXANE is used as a monomer in the production of polymers, which are essential in creating a variety of materials with specific properties for different applications, such as plastics, elastomers, and resins.
Used in Coatings and Adhesives:
VINYLCYCLOHEXANE is used as a component in the formulation of coatings and adhesives, enhancing their performance characteristics, such as adhesion, durability, and resistance to environmental factors.
Used in Solvent Applications:
Due to its chemical properties, VINYLCYCLOHEXANE is used as a solvent in various industrial processes, including the extraction, purification, and separation of different compounds.

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 3652, 1967 DOI: 10.1021/ja00990a061The Journal of Organic Chemistry, 47, p. 1983, 1982 DOI: 10.1021/jo00349a038Synthesis, p. 446, 1979 DOI: 10.1055/s-1979-28713

Flammability and Explosibility

Flammable

InChI:InChI=1/C8H14/c1-2-8-6-4-3-5-7-8/h2,8H,1,3-7H2

Synthetic route

1-<2-trimethylsilyl)ethyl>cyclohexanol (81372-29-4) → vinylcyclohexane (695-12-5)

Conditions	Yield
With borontrifluoride acetic acid In dichloromethane at 25℃; for 0.0833333h;	95%

2-cyclohexylacetylene (931-48-6) → vinylcyclohexane (695-12-5)

Conditions	Yield
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 + cyclohexanecarbaldehyde (2043-61-0) → vinylcyclohexane (695-12-5)

Conditions	Yield
With trifluoroacetic anhydride	76%

Methylenetriphenylphosphorane (19493-09-5) + cyclohexanecarbaldehyde (2043-61-0) → vinylcyclohexane (695-12-5) + Triphenylphosphine oxide (791-28-6)

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

C10H15O2P + cyclohexanecarbaldehyde (2043-61-0) → vinylcyclohexane (695-12-5)

Conditions	Yield
In 1,4-dioxane at 120℃; for 15h; Schlenk technique; Inert atmosphere;	65%

methyl trifluoromethanesulfonate (333-27-7) + cyclohexanecarbaldehyde (2043-61-0) → vinylcyclohexane (695-12-5)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In acetonitrile Wittig Olefination; Inert atmosphere; Glovebox; Electrochemical reaction;	57%

acetophenone (98-86-2) → styrene (292638-84-7) + vinylcyclohexane (695-12-5) + ethylbenzene (100-41-4)

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

vinylidenecyclohexane (5664-20-0) → vinylcyclohexane (695-12-5) + ethylidenecyclohexane (1003-64-1)

Conditions	Yield
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) + tri-n-butyl(vinyl)tin (7486-35-3) → vinylcyclohexane (695-12-5)

Conditions	Yield
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) → vinylcyclohexane (695-12-5) + ethyl-cyclohexane (1678-91-7) + ethylbenzene (100-41-4)

Conditions	Yield
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) → vinylcyclohexane (695-12-5)

Conditions	Yield
at 480℃;

1-cyclohexylethan-1-yl acetate (13487-27-9) → vinylcyclohexane (695-12-5) + ethylidenecyclohexane (1003-64-1)

Conditions	Yield
at 450℃;

(2-iodoethyl)cyclohexane (80203-35-6) → vinylcyclohexane (695-12-5)

Conditions	Yield
With quinoline

dithiocarbonic acid O-(1-cyclohexyl-ethyl ester)-S-methyl ester (99977-91-0) → vinylcyclohexane (695-12-5) + ethylidenecyclohexane (1003-64-1)

Conditions	Yield
at 250℃;

Cyclohexyloxirane (3483-39-4) → vinylcyclohexane (695-12-5) + rac-1-cyclohexylethanol (1193-81-3)

Conditions	Yield
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) + cyclohexane (110-82-7) → vinylcyclohexane (695-12-5)

Conditions	Yield
	19 % Chromat.

2-cyclohexylacetylene (931-48-6) → vinylcyclohexane (695-12-5) + octane (111-65-9)

Conditions	Yield
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) → vinylcyclohexane (695-12-5) + 1-ethylcyclohexene (1453-24-3) + ethylidenecyclohexane (1003-64-1) + 4-ethylcyclohexene (3742-42-5, 75382-76-2) + 3-ethyl-1-cyclohexene (2808-71-1)

Conditions	Yield
trans-carbonylchlorobis(trimethylphosphine)rhodium under 50 Torr; for 72h; Mechanism; Irradiation;

(E)-cyclooctene (931-89-5) → (Z)-Cyclooctene (931-88-4, 931-87-3) + vinylcyclohexane (695-12-5) + 1,7-Octadiene (3710-30-3)

Conditions	Yield
at 512℃; Rate constant; further temperatures;

4-ethenylcyclohexene (100-40-3) → vinylcyclohexane (695-12-5)

Conditions	Yield
With η5-C9H11Fe(CO)2(isobutylene)+BF-; hydrogen; sodium iodide; palladium on activated charcoal Multistep reaction;

Di-(cyclohexyl)-n-butylboran (6917-84-6) + vinyl magnesium bromide (1826-67-1) → 1-hexene (592-41-6) + vinylcyclohexane (695-12-5)

Conditions	Yield
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) → vinylcyclohexane (695-12-5)

Conditions	Yield
With lithium aluminium tetrahydride; aluminium trichloride; lithium 1.) Et2O, 2.) THF; Yield given. Multistep reaction;

2-cyclohexylpropanoic acid (6051-13-4) → vinylcyclohexane (695-12-5) + ethylidenecyclohexane (1003-64-1)

Conditions	Yield
With pyridine; lead(IV) acetate; copper diacetate In benzene for 4h; Heating;

cyclohexyl ethyl acetate (21722-83-8) → vinylcyclohexane (695-12-5) + acetic acid (64-19-7)

Conditions	Yield
at 400℃; Kinetics; Thermodynamic data; var. temp., pressure; ΔH(excit.);

rac-1-cyclohexylethanol (1193-81-3) → vinylcyclohexane (695-12-5) + ethylidenecyclohexane (1003-64-1)

Conditions	Yield
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) + C16H20(2)H2O → vinylcyclohexane (695-12-5) + (1R,2R)-2-Cyclohexyl-1-phenyl-cyclobutanol + (1R,2S)-2-Cyclohexyl-1-phenyl-cyclobutanol + acetophenone (98-86-2)

Conditions	Yield
at 30℃; Product distribution; Irradiation; Norrish II photoreactivity; different solvents, different temperatures;

(2-cyclohexylidene-ethyl)dimethyl(phenyl)silane (79753-67-6) → vinylcyclohexane (695-12-5)

Conditions	Yield
With trifluoroacetic acid In tetrachloromethane for 20h; Ambient temperature;	95 % Spectr.

bicyclo<5.1.0>octan-2-one tosylhydrazone (73733-09-2) → vinylcyclohexane (695-12-5) + 1-octen-7-yne (65909-92-4) + bicyclo<4.2.0>oct-6-ene (37680-26-5)

Conditions	Yield
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) → vinylcyclohexane (695-12-5) + exo-7-methylbicyclo<4.1.0>heptane (14135-43-4)

Conditions	Yield
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 → vinylcyclohexane (695-12-5)

Conditions	Yield
With triphenylstannane for 24h; Irradiation;

vinylcyclohexane (695-12-5) → 1-cyclohexylethane-1,2-diol (61414-09-3, 87858-06-8, 125874-67-1, 59411-58-4)

Conditions	Yield
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) → C8H14O

Conditions	Yield
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) → Cyclohexyloxirane (3483-39-4)

Conditions	Yield
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) + benzoic acid (65-85-0) → 2-bromo-2-cyclohexylethyl benzoate (1403879-55-9)

Conditions	Yield
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) + Dimethyl phosphite (868-85-9) → dimethyl (2-cyclohexylethyl)phosphonate

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In neat (no solvent) for 0.5h; Solvent; UV-irradiation;	99%

vinylcyclohexane (695-12-5) → ethylidenecyclohexane (1003-64-1)

Conditions	Yield
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) + 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

Conditions	Yield
With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 135℃; for 12h;	98%

vinylcyclohexane (695-12-5) + phenylphosphinic acid (1779-48-2) → (2-cyclohexylethyl)(phenyl)phosphinic acid

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In water for 2h; Solvent; UV-irradiation; Green chemistry;	98%

vinylcyclohexane (695-12-5) + sodium benzenesulfonate (873-55-2) → ((2-cyclohexylethyl)sulfonyl)benzene (126002-58-2)

Conditions	Yield
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) + (E)-1-phenyl-N-(1-phenylethylidene)methanamine (14428-98-9, 98325-59-8, 98359-08-1) → 1-[2-(2-cyclohexyl-ethyl)-phenyl]-ethanone

Conditions	Yield
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) + 4-methoxy-phenol (150-76-5) → 4-methoxy-2-(1-cyclohexylethyl)phenol (1173929-13-9)

Conditions	Yield
With decacarbonyldirhenium(0) In toluene at 150℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;	97%

vinylcyclohexane (695-12-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-cyclohexyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethane

Conditions	Yield
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) + Diphenylphosphine oxide (4559-70-0) → (2-cyclohexylethyl)diphenylphosphine oxide

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In N,N-dimethyl-formamide for 2h; Solvent; UV-irradiation; Green chemistry;	97%

vinylcyclohexane (695-12-5) + ethyl 2,2-difluoro-2-iodoacetate (7648-30-8) → ethyl 4-cyclohexyl-2,2-difluoro-4-iodobutanoate

Conditions	Yield
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) + iodotrifluoromethane (2314-97-8) → C9H13F3

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

Conditions	Yield
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) + 2-pyridylmethyl formate (401515-97-7) → pyridin-2-ylmethyl 3-cyclohexylpropanoate

Conditions	Yield
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) + Trichloroacetyl chloride (76-02-8) → 2,2-dichloro-3-(cyclohexyl)cyclobutanone (1029080-53-2)

Conditions	Yield
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) + 6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione (1104636-73-8) → 2-(2-cyclohexylvinyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

Conditions	Yield
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) + 2,2-dimethyl-3,4-dihydro-2H-naphthalen-1-one (2977-45-9) → C20H28O

Conditions	Yield
With Fe(PMe3)4 at 70℃; for 20h; Inert atmosphere; regioselective reaction;	96%

vinylcyclohexane (695-12-5) → [1-chloro-2-(pentafluoro-λ6-sulfanyl)ethyl]cyclohexane (1263301-67-2)

Conditions	Yield
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) + vinylcyclohexane (695-12-5) → 3,3'-bis(2-cyclohexylethyl)-2,2'-bipyridine (1402856-01-2)

Conditions	Yield
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) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) → (3,3,4,4,5,5,6,6,6-nonafluoro-1-iodohexyl)cyclohexane (1464148-71-7)

Conditions	Yield
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) + diphenylsilane (775-12-2) → (2-cyclohexylethyl)diphenylsilane

Conditions	Yield
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) → 1,2-dibromo-1-cyclohexylethane (81602-60-0)

Conditions	Yield
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) + o-iodoacetanilide (19591-17-4) → 1-(3-cyclohexylindolin-1-yl)ethan-1-one

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

Conditions	Yield
With C47H47N2O2Sc In benzene-d6 at 75℃; Schlenk technique; Sealed tube; enantioselective reaction;	94%

vinylcyclohexane (695-12-5) + N-(2-methylbenzoyl)-8-aminoquinoline (1182669-71-1) → 2-(2-cyclohexylethyl)-6-methyl-N-(quinolin-8-yl)benzamide

Conditions	Yield
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) + ethyl 2-cyanoacetate (105-56-6) → 2-cyano-4-cyclohexyl-butyric acid ethyl ester

Conditions	Yield
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);

Upstream product

• 21722-83-8 cyclohexyl ethyl acetate 
• 13487-27-9 1-cyclohexylethan-1-yl acetate 
• 80203-35-6 (2-iodoethyl)cyclohexane 
• 99977-91-0 dithiocarbonic acid O-(1-cyclohexyl-ethyl ester)-S-methyl ester 
• 3483-39-4 Cyclohexyloxirane 
• 100-42-5 styrene 
• 108-05-4 vinyl acetate 
• 110-82-7 cyclohexane 
• 5664-20-0 vinylidenecyclohexane 
• 931-48-6 2-cyclohexylacetylene 
• 1678-91-7 ethyl-cyclohexane 
• 931-89-5 (E)-cyclooctene 
• 100-40-3 4-ethenylcyclohexene 
• 6917-84-6 Di-(cyclohexyl)-n-butylboran 

Downstream Products

• 81602-60-0 1,2-dibromo-1-cyclohexylethane 
• 100-41-4 ethylbenzene 
• 100314-83-8 trans-2-cyclohexyl-cyclopropanecarboxylic acid ethyl ester 
• 58070-62-5 1-Chlor-1-cyclohexyl-3-methoxy-propan 
• 40745-20-8 dimethyl 2-cyclohexylsuccinate 
• 71195-17-0 dimethyl ester of trans-2'-carboxycyclohexanepropanoic acid 
• 28239-41-0 (1,3,3,3-tetrachloropropyl)cyclohexane 
• 28239-43-2 Trichloro-1,1,1-cyclohexyl-3-propan 
• 7087-57-2 2,2-Dibrom-1-cyclohexyl-cyclopropan 
• 7077-71-6 2-(2-cyclohexyl-ethyl)-octanoic acid 
• 1940-19-8 1-vinylcyclohexanol 
• 4065-85-4 1-Hydroperoxy-1-vinylcyclohexan 
• 4442-79-9 cyclohexylethan-1-ol 
• 30011-03-1 N,N-Dimethyl-(2-chlorcyclohexyl-oxymethylen)-immoniumchlorid 

Relevant articles and documents

Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydroboration and Dehydroboration

We report a dehydroboration process that can be coupled with chain-walking hydroboration to create a one-pot, contra-thermodynamic, short-or long-range isomerization of internal olefins to terminal olefins. This dehydroboration occurs by a sequence comprising activation with a nucleophile, iodination, and base-promoted elimination. The isomerization proceeds at room temperature without the need for a fluoride base, and the substrate scope of this isomerization is expanded over those of previous isomerizations we have reported with silanes.

Preparation method of vinylcyclohexane

The invention discloses a preparation method of vinylcyclohexane, and belongs to the technical field of organic synthesis. Cyclohexyl ketone is used as a raw material, and is firstly condensed with 2, 4, 6-triisopropylbenzenesulfonyl hydrazide to obtain 1-acetocyclohexane-2, 4, 6-triisopropylbenzenesulfonyl hydrazone; and reaction is carried out in the presence of an inorganic base and a non-nucleophilic strong base to obtain vinylcyclohexane. The method has the advantages of two-step reaction, simple route, high area selection and relatively easy product separation, and a certain amount of polymerization inhibitor needs to be added in the product distillation process to prevent polymerization in the distillation process.

A Systems Approach to a One-Pot Electrochemical Wittig Olefination Avoiding the Use of Chemical Reductant or Sacrificial Electrode

An unprecedented one-pot fully electrochemically driven Wittig olefination reaction system without employing a chemical reductant or sacrificial electrode material to regenerate triphenylphosphine (TPP) from triphenylphosphine oxide (TPPO) and base-free in situ formation of Wittig ylides, is reported. Starting from TPPO, the initial step of the phosphoryl P=O bond activation proceeds through alkylation with RX (R=Me, Et; X=OSO2CF3 (OTf)), affording the corresponding [Ph3POR]+X? salts which undergo efficient electroreduction to TPP in the presence of a substoichiometric amount of the Sc(OTf)3 Lewis acid on a Ag-electrode. Subsequent alkylation of TPP affords Ph3PR+ which enables a facile and efficient electrochemical in situ formation of the corresponding Wittig ylide under base-free condition and their direct use for the olefination of various carbonyl compounds. The mechanism and, in particular, the intriguing role of Sc3+ as mediator in the TPPO electroreduction been uncovered by density functional theory calculations.