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106-87-6

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106-87-6 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 106-87-6 differently. You can refer to the following data:
1. colourless liquid. Combustible.
2. Vinyl cyclohexene dioxide is a colorless liquid

Uses

Different sources of media describe the Uses of 106-87-6 differently. You can refer to the following data:
1. Vinylcyclohexene dioxide (VCD) is used to study toxicity as an ovotoxin,and it's also used to understand its mechanisms of toxicity towards ovarian follicles and effects on epithelial differentiation.
2. As a chemical intermediate and as a reactive diluent for diepoxides and epoxy resins.
3. Vinylcyclohexene dioxide (VCD) may be used to study and understand its effect on ovarian follicles and effects on epithelial differentiation.

Production Methods

VCHD is manufactured by epoxidation of 4-vinylcyclohexene with peroxyacetic acid .

Definition

ChEBI: The diepoxide of 4-vinylcyclohexene.

General Description

Clear colorless liquid. Sets to glass at -67°F. Faint olefinic odor.

Air & Water Reactions

Water soluble. Hydrolyzes slowly in water.

Reactivity Profile

4-VINYLCYCLOHEXENE DIOXIDE reacts with active hydrogen compounds (such as alcohols and amines). . Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

Hazard

Toxic by ingestion and skin absorption, strong irritant to skin and tissue. Female and male reproductive damage. Possible carcinogen.

Health Hazard

Vinyl cyclohexene dioxide (VCD) is an irritant to the skin, eyes, and respiratory system. It is ovotoxic and carcinogenic in experimental animals.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by unspecified route. Moderately toxic by ingestion and skin contact. Mildly toxic by inhalation. Experimental reproductive effects. Mutation data reported. A severe skin irritant.Combustible when exposed to heat or flame. To fight fire, use water, foam, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

This material is used as a monomer in the production of epoxy resins for coatings and adhesives; as a chemical intermediate and as a reactive diluent.

Carcinogenicity

4-Vinyl-1-cyclohexene diepoxide is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity fromstudies in experimental animals.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Incompatibilities

When heated or in contact with catalysts, epoxides may cause violent polymerization. Epoxides are incompatible with reducing agents and oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. May react, possibly violently, with water in the presence of acid and other catalysts. Reacts with alcohols, amines and other active hydrogen compounds. Slowly hydrolyzes in water.

Waste Disposal

Concentrated waste containing no peroxides: discharge liquid at a controlled rate near a pilot flame. Concentrated waste containing peroxides: perforation of a container of the waste from a safe distance followed by open burning.

Check Digit Verification of cas no

The CAS Registry Mumber 106-87-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 106-87:
(5*1)+(4*0)+(3*6)+(2*8)+(1*7)=46
46 % 10 = 6
So 106-87-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H12O2/c1-2-6-7(10-6)3-5(1)8-4-9-8/h5-8H,1-4H2

106-87-6 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Sigma

  • (94956)  Vinylcyclohexenedioxide  purum, for electron microscopy, mixture of isomers, ≥96.0% (GC)

  • 106-87-6

  • 94956-100ML

  • 4,278.69CNY

  • Detail
  • Sigma

  • (94956)  Vinylcyclohexenedioxide  purum, for electron microscopy, mixture of isomers, ≥96.0% (GC)

  • 106-87-6

  • 94956-250ML

  • 8,558.55CNY

  • Detail

106-87-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-vinylcyclohexene dioxide

1.2 Other means of identification

Product number -
Other names 4-vinylcyclohexene diepoxide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106-87-6 SDS

106-87-6Synthetic route

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

4-vinylcyclohexene dioxide
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.;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

C8H12O

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%
1,1,3,3-tetrachloropropanone
632-21-3

1,1,3,3-tetrachloropropanone

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

D

tetrachloroacetone hydrate
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
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

7,8-Epoxy-1-Cyclohexene
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;
4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
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;
methanol
67-56-1

methanol

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

A

4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

B

1,2-Epoxy-4-vinylcyclohexane
106-86-5

1,2-Epoxy-4-vinylcyclohexane

C

7,8-Epoxy-1-Cyclohexene
5116-65-4

7,8-Epoxy-1-Cyclohexene

D

cyclohex-3-enyl acetaldehyde
24480-99-7

cyclohex-3-enyl acetaldehyde

F

2-Methoxy-5-vinyl-cyclohexanol

2-Methoxy-5-vinyl-cyclohexanol

G

C9H16O2
1243451-21-9

C9H16O2

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

4-vinylcyclohexene dioxide

carbon dioxide
124-38-9

carbon dioxide

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

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%
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

carbon dioxide
124-38-9

carbon dioxide

C10H12O6

C10H12O6

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

4-vinylcyclohexene dioxide

carbon dioxide
124-38-9

carbon dioxide

C10H12O6

C10H12O6

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

4-vinylcyclohexene dioxide

carbon dioxide
124-38-9

carbon dioxide

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

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
106-87-6

4-vinylcyclohexene dioxide

n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

6-pentyl-7-oxabicyclo<3.2.1>octan-2-ol

6-pentyl-7-oxabicyclo<3.2.1>octan-2-ol

Conditions
ConditionsYield
With triphenylphosphine; copper(I) bromide 1.) THF, Et2O, 0 deg C, 30 min, 2.) THF, Et2O, 0 deg C, 2 h; Yield given; Multistep reaction;
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

polymer, from photosensitized cationic polymerization; monomer(s): 4-vinylcyclohexene dioxide

polymer, from photosensitized cationic polymerization; monomer(s): 4-vinylcyclohexene dioxide

Conditions
ConditionsYield
With 10-(2-(vinyloxy)ethyl)-10H-phenothiazine; (4-n-decyloxyphenyl) phenyliodonium hexafluoroantimonate at 20℃; Product distribution; Further Variations:; Reagents; UV-irradiation;
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

4-(1,2-dihydroxyethyl)cyclohexane-1,2-diol
5581-28-2

4-(1,2-dihydroxyethyl)cyclohexane-1,2-diol

Conditions
ConditionsYield
With sulfuric acid In water; acetone
4-vinylcyclohexene dioxide
106-87-6

4-vinylcyclohexene dioxide

2,2,4-trimethyl-decahydro-quinoline
65125-45-3

2,2,4-trimethyl-decahydro-quinoline

1-[2'-hydroxy-2'-(3,4-epoxycyclohexyl)ethyl]-2,2,4-trimethyldecahydroquinoline
65825-48-1

1-[2'-hydroxy-2'-(3,4-epoxycyclohexyl)ethyl]-2,2,4-trimethyldecahydroquinoline

Conditions
ConditionsYield
With Hg In ethylene glycol

106-87-6Relevant articles and documents

Covalent heterogenization of a discrete Mn(II) Bis-Phen complex by a metal-template/metal-exchange method: An epoxidation catalyst with enhanced reactivity

Terry, Tracy J.,Daniel,Stack

, p. 4945 - 4953 (2008)

Considerable attention has been devoted to the immobilization of discrete epoxidation catalysts onto solid supports due to the possible benefits of site isolation such as increased catalyst stability, catalyst recycling, and product separation. A synthetic metal-template/metal-exchange method to imprint a covalently attached bis-1,10-phenanthroline coordination environment onto high-surface area, mesoporous SBA-15 silica is reported herein along with the epoxidation reactivity once reloaded with manganese. Comparisons of this imprinted material with material synthesized by random grafting of the ligand show that the template method creates more reproducible, solution-like bis-1,10-phenanthroline coordination at a variety of ligand loadings. Olefin epoxidation with peracetic acid shows the imprinted manganese catalysts have improved product selectivity for epoxides, greater substrate scope, more efficient use of oxidant, and higher reactivity than their homogeneous or grafted analogues independent of ligand loading. The randomly grafted manganese catalysts, however, show reactivity that varies with ligand loading while the homogeneous analogue degrades trisubstituted olefins and produces trans-epoxide products from cis-olefins. Efficient recycling behavior of the templated catalysts is also possible.

METHOD FOR PRODUCING EPOXY COMPOUND

-

Paragraph 0089-0091, (2021/11/05)

The invention provides a method for producing an epoxy compound by hydrogen peroxide using an organic compound having a carbon-carbon double bond as a raw material, wherein a by-product is suppressed from being generated and the epoxy compound is produced in a high yield. In particular, the invention provides a method for producing an epoxy compound involving oxidizing a carbon-carbon double bond in an organic compound with hydrogen peroxide in the presence of a catalyst, wherein the catalyst comprises a tungsten compound; a phosphoric acid, a phosphonic acid or salts thereof; and an onium salt having an alkyl sulfate ion represented by formula (I) as an anion: wherein R1 is a linear or branched aliphatic hydrocarbon group having 1 to 18 carbons, which may be substituted with 1 to 3 phenyl groups.

Safe, environment-friendly and controllable synthetic process of di-epoxide

-

Paragraph 0152-0168, (2019/10/01)

The invention relates to the field of synthesis of epoxide, and more specifically, relates to a safe, environment-friendly and controllable synthetic process of di-epoxide. The synthetic process of the di-epoxide at least comprises the following steps: mixing diolefin, carboxylic acids, basic salt and solvent, and cooling; dropwise adding a hydrogen peroxide solution for 1-12 h; standing for layering to obtain a lower layer organic phase-1, washing the organic phase-1 with a cleaning solution, and standing for layering to obtain a lower layer organic phase-2; purifying. The reaction system ofthe synthetic process is simple, environmentally friendly, safe and controllable, is low in production cost, and can meet the requirements of technical economy; the prepared di-epoxide is high in purity and yield and low in solvent content, chroma and halogen content, and is suitable for large-scale industrial production.

2,2,2-Trifluoroacetophenone: An organocatalyst for an environmentally friendly epoxidation of alkenes

Limnios, Dimitris,Kokotos, Christoforos G.

, p. 4270 - 4276 (2014/06/09)

A cheap, mild, fast, and environmentally friendly oxidation of olefins to the corresponding epoxides is reported using polyfluoroalkyl ketones as efficient organocatalysts. Namely, 2,2,2-trifluoroacetophenone was identified as an improved organocatalyst for the epoxidation of alkenes. Various olefins, mono-, di-, and trisubstituted, are epoxidized chemoselectively in high to quantitative yields utilizing 2-5 mol % catalyst loading and H2O 2 as the green oxidant.

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