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4-Vinylcyclohexene dioxide

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Name

4-Vinylcyclohexene dioxide

EINECS 203-437-7
CAS No. 106-87-6 Density 1.228 g/cm3
PSA 25.06000 LogP 0.95270
Solubility moderate Melting Point -55°C
Formula C8H12O2 Boiling Point 226.999 °C at 760 mmHg
Molecular Weight 140.182 Flash Point 86.412 °C
Transport Information N/A Appearance colourless liquid
Safety 23-24-45 Risk Codes 23/24/25-68/20/21/22-68
Molecular Structure Molecular Structure of 106-87-6 (4-VINYLCYCLOHEXENE DIOXIDE) Hazard Symbols ToxicT
Synonyms

1-(Epoxyethyl)-3,4-epoxycyclohexane;1-Vinyl-3-cyclohexene dioxide;3-(1,2-Epoxyethyl)-7-oxabicyclo[4.1.0]heptane;3-(Epoxyethyl)-7-oxabicyclo[4.1.0]heptane;4-(1,2-Epoxyethyl)-1,2-epoxycyclohexane;4-Vinyl-1,2-cyclohexene diepoxide;4-Vinyl-1-cyclohexenediepoxide;4-Vinyl-1-cyclohexene dioxide;4-Vinylcyclohexene diepoxide;4-Vinylcyclohexene dioxide;Chissonox 206 monomer;Diluent 6206;NSC 54752;NSC61281;NSC 7583;Vinylcyclohexene diepoxide;7-Oxabicyclo[4.1.0]heptane,3-(epoxyethyl)- (6CI,8CI);7-Oxabicyclo[4.1.0]heptane, 3-oxiranyl- (9CI);1,2-Epoxy-4-(epoxyethyl)cyclohexane;

Article Data 21

4-Vinylcyclohexene dioxide Synthetic route

100-40-3

4-ethenylcyclohexene

106-87-6

4-vinylcyclohexene dioxide

Conditions
ConditionsYield
With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide In acetonitrile; tert-butyl alcohol at 20℃; for 1h; Green chemistry;88%
With fluorosulfonyl fluoride; dihydrogen peroxide; potassium carbonate In 1,4-dioxane; water at 20℃; for 1h;81%
With hypochloric acid Behandeln des Reaktionsproduktes mit wss. Natronlauge.;
100-40-3

4-ethenylcyclohexene

A

106-87-6

4-vinylcyclohexene dioxide

C8H12O

Conditions
ConditionsYield
With C20H26FeN4(2+)*2CF3O3S(1-); dihydrogen peroxide; acetic acid In acetonitrile at 0℃; for 0.166667h; regioselective reaction;A n/a
B 74%
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

106-87-6

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

106-87-6

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;
67-56-1

methanol

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

24480-99-7

cyclohex-3-enyl acetaldehyde

F

2-Methoxy-5-vinyl-cyclohexanol

G

1243451-21-9

C9H16O2

Conditions
ConditionsYield
With dihydrogen peroxide In water at 64.84℃; for 2h; regioselective reaction;
106-87-6

4-vinylcyclohexene dioxide

124-38-9

carbon dioxide

cis-5-(2-oxo-1,3-dioxolan-4-yl)hexahydrobenzo[d][1,3]dioxol-2-one

Conditions
ConditionsYield
With C20H13FeN2O5; tetrabutylammomium bromide at 100℃; under 3750.38 - 7500.75 Torr; for 12h; Sealed tube;99%
106-87-6

4-vinylcyclohexene dioxide

124-38-9

carbon dioxide

C10H12O6

Conditions
ConditionsYield
With tetrabutylammomium bromide In neat (no solvent) at 100℃; for 12h; chemoselective reaction;99%
106-87-6

4-vinylcyclohexene dioxide

124-38-9

carbon dioxide

C10H12O6

Conditions
ConditionsYield
With calcium iodide In neat (no solvent) at 90℃; under 37503.8 Torr; for 48h; diastereoselective reaction;93%
106-87-6

4-vinylcyclohexene dioxide

124-38-9

carbon dioxide

4-(7-oxabicyclo[4.1.0]heptan-3-yl)-1,3-dioxolan-2-one

Conditions
ConditionsYield
With 18-crown-6 ether; calcium iodide In neat (no solvent) at 23℃; under 760.051 Torr; for 24h;92%

4-Vinylcyclohexene dioxide Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 11 ,1976,p. 141.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.

4-Vinylcyclohexene dioxide Standards and Recommendations

OSHA PEL: TWA 10 ppm (skin)
ACGIH TLV: TWA 0.1 ppm; Animal Carcinogen
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen

4-Vinylcyclohexene dioxide Specification

The Vinyl cyclohexene dioxide , with cas registry number of 106-87-6, is also called 4-Vinylcyclohexene dioxide ; 4-Vinyl-1-cyclohexene diepoxide ; 3-(Oxiran-2-yl)-7-oxabicyclo[4.1.0]heptane . Its IUPAC name is 4-(oxiran-2-yl)-7-oxabicyclo[4.1.0]heptane . And the systematic name is named as 3-(oxiran-2-yl)-7-oxabicyclo[4.1.0]heptane . Vinyl cyclohexene dioxide is incompatible with strong oxidizing agents, alcohols, amines and other compounds containg an active hydrogen. It hydrolyzes slowly in water.

Physical properties of Vinyl cyclohexene dioxide : (1) H bond acceptors: 2; (2) H bond donors: 0; (3) Freely Rotating Bonds: 1; (4) Index of Refraction: 1.546; (5) Molar Refractivity: 36.2 cm3; (6) Molar Volume: 114.1 cm3; (7) Surface Tension: 50.5 dyne/cm; (8) Enthalpy of Vaporization: 44.47 kJ/mol; (9) Vapour Pressure: 0.119 mmHg at 25°C; (10) Refractive index: n20/D 1.477(lit.).

Uses of Vinyl cyclohexene dioxide : This compound is used as a chemical intermediate. It is also used in the preparation of polyethylene glycol monomer that contains no active epoxy group.

When you are using this chemical, please be cautious about it as the following:
The Vinyl cyclohexene dioxide is harmful and toxic by inhalation, in contact with skin and if swallowed. When use it, avoid contact with skin and eyes and do not breathe vapour. It also has the possible risk of irreversible effects.

You can still convert the following datas into molecular structure:
(1) SMILES:O3C(C1CC2OC2CC1)C3;
(2) InChI:InChI=1/C8H12O2/c1-2-6-7(10-6)3-5(1)8-4-9-8/h5-8H,1-4H2;
(3) InChIKey:OECTYKWYRCHAKR-UHFFFAOYAP

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo skin 3216mg/kg (3216mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
National Toxicology Program Technical Report Series. Vol. NTP-TR-362, Pg. 1989,
rabbit LD50 skin 620uL/kg (0.62mL/kg)   Union Carbide Data Sheet. Vol. 9/19/1972,
rabbit LD50 unreported 680ug/kg (0.68mg/kg) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Bolletino della Societe Italiana di Biologia Sperimentale. Vol. 56, Pg. 1803, 1980.
rat LC50 inhalation 800ppm/4H (800ppm)   Shell Chemical Company. Unpublished Report. Vol. -, Pg. 9, 1961.
rat LD50 oral 2130mg/kg (2130mg/kg)   Shell Chemical Company. Unpublished Report. Vol. -, Pg. 9, 1961.

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