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1,2-Epoxy-4-vinylcyclohexane

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Name

1,2-Epoxy-4-vinylcyclohexane

EINECS 203-436-1
CAS No. 106-86-5 Density 1.06 g/cm3
PSA 12.53000 LogP 1.73990
Solubility N/A 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;

Article Data 52

1,2-Epoxy-4-vinylcyclohexane Synthetic route

100-40-3

4-ethenylcyclohexene

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%
632-21-3

1,1,3,3-tetrachloropropanone

100-40-3

4-ethenylcyclohexene

A

106-87-6

4-vinylcyclohexene dioxide

B

106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

5116-65-4

7,8-Epoxy-1-Cyclohexene

D

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
100-40-3

4-ethenylcyclohexene

A

106-86-5

1,2-Epoxy-4-vinylcyclohexane

B

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;
79-21-0

peracetic acid

100-40-3

4-ethenylcyclohexene

106-86-5

1,2-Epoxy-4-vinylcyclohexane

100-40-3

4-ethenylcyclohexene

A

106-87-6

4-vinylcyclohexene dioxide

B

106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

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;
100-40-3

4-ethenylcyclohexene

A

106-86-5

1,2-Epoxy-4-vinylcyclohexane

B

5116-65-4

7,8-Epoxy-1-Cyclohexene

C

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;
100-40-3

4-ethenylcyclohexene

A

106-86-5

1,2-Epoxy-4-vinylcyclohexane

B

5537-04-2

4-Vinylcyclohex-1-en-4-ol

88301-28-4

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

64248-92-6, 81457-32-1, 88301-27-3

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

64248-92-6, 81457-32-1, 88301-27-3

cis-4-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
100-40-3

4-ethenylcyclohexene

A

106-86-5

1,2-Epoxy-4-vinylcyclohexane

24779-55-3

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

24779-57-5

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

D

3736-26-3

4-Hydroperoxy-4-vinylcyclohex-1-en

24779-56-4

trans-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.
100-40-3

4-ethenylcyclohexene

64-19-7

acetic acid

A

106-86-5

1,2-Epoxy-4-vinylcyclohexane

B

31646-64-7

3,4-dihydroxy-1-vinylcyclohexane

C

4-vinylcyclohexanediol-1,2 monoacetate

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

4-ethenylcyclohexene

A

106-87-6

4-vinylcyclohexene dioxide

B

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;

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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