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Vinylcyclohexane

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Name

Vinylcyclohexane

EINECS 211-779-3
CAS No. 695-12-5 Density 0.865 g/cm3
PSA 0.00000 LogP 2.75270
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;

Article Data 113

Vinylcyclohexane Synthetic route

81372-29-4

1-<2-trimethylsilyl)ethyl>cyclohexanol

695-12-5

vinylcyclohexane

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

2-cyclohexylacetylene

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

2043-61-0

cyclohexanecarbaldehyde

695-12-5

vinylcyclohexane

Conditions
ConditionsYield
With trifluoroacetic anhydride76%
19493-09-5

Methylenetriphenylphosphorane

2043-61-0

cyclohexanecarbaldehyde

A

695-12-5

vinylcyclohexane

B

791-28-6

Triphenylphosphine oxide

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

C10H15O2P

2043-61-0

cyclohexanecarbaldehyde

695-12-5

vinylcyclohexane

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

methyl trifluoromethanesulfonate

2043-61-0

cyclohexanecarbaldehyde

695-12-5

vinylcyclohexane

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

acetophenone

A

292638-84-7

styrene

B

695-12-5

vinylcyclohexane

C

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%
5664-20-0

vinylidenecyclohexane

A

695-12-5

vinylcyclohexane

B

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;
24371-94-6

cyclohexylmercury chloride

7486-35-3

tri-n-butyl(vinyl)tin

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%

A

695-12-5

vinylcyclohexane

B

1678-91-7

ethyl-cyclohexane

C

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%

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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