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4-Vinyl-1-cyclohexene

CAS：100-40-3
MW:108.18088
MF：C8H12

Colorless liquid. Floats on water. Temperatures above 80F (26.6C) and prolonged exposure to oxygen-containing gases should be avoided because these conditions lead to discoloration and gum formation. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: 4-Vinyl-1-cyclohexene

1.2 Synonyms: 4-Ethenylcyclohexene; 4-ethenyl-Cyclohexene; 4-VCH; 4-Vinyl-1-cycl; 4-vinyl-1-cyclohexen; 4-Vinyl-1-cyclohexene,stabilized; 4-Vinylcyclohex-1-ene; 4-vinyl-cyclohexen; 4-Vinylcyclohexene; Butadiene dimer; Cyclohexene, 4-ethenyl-; EINECS 202-848-9; L6UTJ D1U1; MFCD00001576; NSC 15760; Vinyl-1-cyclohex;

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1.3 CAS No.: 100-40-3

1.4 CID: 7499

1.5 EINECS: 202-848-9 C6H9CH=CH2

1.6 Molecular Formula: C8H12

1.7 Inchi: InChI=1S/C8H12/c1-2-8-6-4-3-5-7-8/h2-4,8H,1,5-7H2

1.8 InChkey: BBDKZWKEPDTENS-UHFFFAOYSA-N

1.9 Canonical Smiles: C=CC1CCC=CC1

1.10 Isomers Smiles: C=CC1CCC=CC1

2. Properties

2.1 Vapour pressure: 3.76 (vs air)

2.2 Solubility: 50mg/L(25 ºC)

2.3 Viscosity: 0.84 mm2/s at 20 °C

2.4 VaporDensity: 3.76 (vs air)

2.5 Appearance: colourless liquid

2.6 Autoignition Temperature: 517 °F (269 °C).

2.7 Chemical Properties: Liquid. Temperaturesabove 80F (26.6C) and prolonged exposureto oxygen-containing gases should be avoidedbecause these conditions lead to discoloration andgum formation.

2.8 Color/Form: Liquid

2.9 Water Solubility: Slightly AUTOIGNITION

2.10 Spectral Properties: Index of refraction: 1.4639 @ 20 deg C
MAX ABSORPTION (ETHANOL): 230 NM (E= 1935)
IR: u API 146 (American Petroleum Institute spectral collection)
1H NMR: VAR 210 (Varian Associates NMR Spectra Catalogue)
MS: NIST 1402 (NIST/EPA/MSDC Mass Spectral database 1990 version); NBS 4444

2.11 Stability: Stable. Flammable (note low flash point). Incompatiblewith strong oxidizing agents, peroxide catalysts. Air-sensitive.

2.12 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Description: Liquid. Temperaturesabove 80F (26.6C) and prolonged exposureto oxygen-containing gases should be avoidedbecause these conditions lead to discoloration andgum formation. 4-Vinyl-1-cyclohexene, a cyclic alkene, is ahighly flammable liquid.Colorless liquid. Floats on water. Temperatures above 80F (26.6C) and prolonged exposure to oxygen-containing gases should be avoided because these conditions lead to discoloration and gum formation.

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3.2 General Description: Colorless liquid. Floats on water. Temperatures above 80F (26.6C) and prolonged exposure to oxygen-containing gases should be avoided because these conditions lead to discoloration and gum formation.

3.3 Potential Exposure: 4-Vinyl-1-cyclohexene is used as anintermediate for the production of vinylcyclohexene dioxide,which is used as a reactive diluent in epoxy resins.Previous uses of 4-vinyl-1-cyclohexene include comonomerin the polymerization of other monomers and for halogenationto polyhalogenated derivatives which are used as flameretardants.

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3.4 Produe Method: 4-Vinylcyclohexene is produced by dimerization of butadiene,as a by-product of chlorination of butadiene, or frombutadieneon long storage.

3.5 Shipping: UN1993 Flammable liquids, n.o.s., HazardClass: 3; Labels: 3-Flammable liquid, Technical NameRequired.

3.6 Usage: Polymers, organic synthesis.

3.7 Waste Disposal: Dissolve or mix the materialwith a combustible solvent and burn in a chemicalincinerator equipped with an afterburner and scrubber.All federal, state, and local environmental regulations mustbe observed. 4-Vinyl-1-cyclohexene Preparation Products And Raw materials Preparation Products

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4. Safety and Handling

4.1 Octanol/Water Partition Coefficient: log Kow = 3.93

4.2 Other Preventative Measures: SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Principles that apply to chem or biochem lab also apply to microbiological & cell-culture labs ... Special consideration should be given to route of admin. ... Safest method of administering volatile carcinogen is by injection of a soln. Admin by topical application, gavage, or intratracheal instillation should be performed under hood. If chem will be exhaled, animals should be kept under hood during this period. Inhalation exposure requires special equipment. ... Unless specifically required, routes of admin other than in the diet should be used. Mixing of carcinogen in diet should be carried out in sealed mixers under fume hood, from which the exhaust is fitted with an efficient particulate filter. Techniques for cleaning mixer & hood should be devised before expt begun. When mixing diets, special protective clothing &, possibly, respirators may be required. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides & fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary. Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with which it can be removed. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ... should ... where possible, be simple & sensitive. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical Carcinogens/

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4.3 Cleanup Methods: PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

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4.4 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/

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4.5 Fire Fighting Procedures: To fight fire, use foam, CO2, dry chemical.

4.6 FirePotential: FLAMMABLE, DANGEROUS FIRE RISK.
DANGEROUS FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME

4.7 Safety Profile: Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Moderately toxic by ingestion and inhalation. MilcU~7 toxic by skin contact. Experimental reproductive effects. Dangerous fire hazard when exposed to heat, flame, or oxidizers. Can react with oxidizers. To fight fire, use foam, CO2, dry chemical.

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4.8 Formulations/Preparations: Grades: Technical, 95%; Pure, 99%; Research.

4.9 Incompatibilities: Vapor may form explosive mixture withair. Hydrolyzes in water. Incompatible with oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates,chlorine, bromine, fluorine, etc.); contact may cause firesor explosions. Keep away from alkaline materials, strongbases, strong acids, oxoacids, epoxides, amines, alcohols.

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4.10 Protective Equipment and Clothing: It is an irritant, and it defats the skin on direct contact.

4.11 Reactivities and Incompatibilities: Can react with oxidizers.
Upon contact with oxygen, VCH undergoes auto-oxidation to produce vinylcyclohexene hydroperoxide. The hydroperoxide can be formed during prolonged storage of butadiene, & further autocondensation leads to 1,2,3,6,1',2',3',6'-octahydrobiphenyl.

4.12 Skin, Eye, and Respiratory Irritations: It is an irritant, and it defats the skin on direct contact.

4.13 Safety: R11:Highlyflammable.;R38:Irritatingtoskin.;R40:Possiblerisksofirreversibleeffects.;R52/53:Harmfultoaquaticorganisms,maycauselong-termadverseeffectsintheaquaticenvironment.;

4.14 Specification: clear colorless to very slightly yellow liquid
Safety Statements:16-33-36/37
16:Keep away from sources of ignition - No smoking
33:Take precautionary measures against static discharges
36/37:Wear suitable protective clothing and gloves

4.15 Toxicity: ORL-RAT LD50 2563 mg kg-1, SKN-RBT LD50 16640 mg kg-1

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H351 Suspected of causing cancer
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

IR : CCl4 solution

IR : liquid film

Raman : 4880 A,200 M,liquid

Mass

7. Synthesis Route

100-40-3Total: 94 Synthesis Route

934-79-2

100-40-3 37 Suppliers

106-99-0 108 Suppliers

100-40-3 37 Suppliers

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8. Precursor and Product

precursor:

106-99-0

934-79-2

product:

106-87-6

695-12-5

923-42-2

106-86-5

1123-84-8

1678-91-7

6671-66-5

7353-76-6

3322-93-8

100-50-5

9. Computed Properties

Molecular Weight：108.18088g/mol
Molecular Formula：C₈H₁₂
Compound Is Canonicalized：True
Exact Mass：2.8
XLogP3-AA：108.093900383
Monoisotopic Mass：108.093900383
Complexity：101
Rotatable Bond Count：1
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：0
Topological Polar Surface Area：0
Heavy Atom Count：：8
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：1
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBwAAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAGAAAAAAADQCAAAAAAAAAAACAACBCAAAAAAAgAAAICAAAAAgAAAIAAQAAAAAAgAAIAAMAAAAOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

BRN: 1901553

职业标准: TLV-TWA 0.1 PPM

Chemical Properties: Liquid. Temperatures above 80F (26.6C) and prolonged exposure to oxygen-containing gases should be avoided because these conditions lead to discoloration and gum formation.

Chemical Properties: 4-Vinyl-1-cyclohexene, a cyclic alkene, is a highly flammable liquid.

Uses: Polymers, organic synthesis.

Uses: As an intermediate in the production of flame retardants, flavors, fragrances, and vinyl cyclohexene dioxide (which itself is used in the manufacture of epoxy resins); found in gases discharged during the process of curing rubber in tire manufacturing.

Production Methods: 4-Vinylcyclohexene is produced by dimerization of butadiene, as a by-product of chlorination of butadiene, or frombutadiene on long storage.

Synthesis Reference(s): Journal of the American Chemical Society, 108, p. 1322, 1986 DOI: 10.1021/ja00266a047
Synthesis, p. 1027, 1984

General Description: Colorless liquid. Floats on water. Temperatures above 80F (26.6C) and prolonged exposure to oxygen-containing gases should be avoided because these conditions lead to discoloration and gum formation.

Air & Water Reactions: Highly flammable. 4-Vinyl-1-cyclohexene oxidizes in air to form hydroperoxides. Slightly soluble in water.

Reactivity Profile: 4-Vinyl-1-cyclohexene can react with oxidizing materials. 4-Vinyl-1-cyclohexene is also incompatible with peroxide catalysts. Prolonged exposure to oxygen-containing gases leads to discoloration and gum formation. .

Health Hazard: Exposure can cause irritation of eyes, nose and throat. High concentrations have a narcotic effect.

Safety Profile: Confirmed carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Moderately toxic by ingestion and inhalation. MilcU~7 toxic by skin contact. Experimental reproductive effects. Dangerous fire hazard when exposed to heat, flame, or oxidizers. Can react with oxidizers. To fight fire, use foam, CO2, dry chemical.

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Potential Exposure: 4-Vinyl-1-cyclohexene is used as an intermediate for the production of vinylcyclohexene dioxide, which is used as a reactive diluent in epoxy resins. Previous uses of 4-vinyl-1-cyclohexene include comonomer in the polymerization of other monomers and for halogenation to polyhalogenated derivatives which are used as flame retardants.

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Carcinogenicity: A dose of 145 g/kg applied to mouse skin for 54 weeks provided weak evidence of carcinogenicity (109). Administration by gavage of doses of 0, 200, or 400 mg/kg body weight, 5 days per week, to groups of 50 F344/N rats for 103 weeks induced a slightly increased incidence of epithelial hyperplasia of the forestomach (1/50; 3/50; 5/47) and squamous cell papillomas or carcinomas (combined) of the skin, in males receiving the highest dose. Low-dose female rats whose survival was more similar to that of the vehicle controls had a marginally increased incidence of adenomas or squamous cell carcinomas (combined) of the clitoral gland. Under these conditions, the 2-year gavage studies in male and female rats were considered inadequate because of extensive and early mortality at the high dose or at body doses and the lack of conclusive evidence of a carcinogenic effect (125a). In female Fisher 344 rats treated with this agent to induce ovarian failure followed by application of the carcinogen dimethylbenzanthracene (DMBA) directly to the ovaries, there resulted tumors in 42% of animals at 3 months and 57% at 5 months (126b). All neoplasms were classified Sertoli–Leydig cell tumors (SLCT). No tumors occurred in animals treated with vehicle or DMBA alone.

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Shipping: UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required.

Incompatibilities: Vapor may form explosive mixture with air. Hydrolyzes in water. Incompatible with 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, amines, alcohols.

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Waste Disposal: Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

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12. Related Questions

: What are the properties and applications of 4-Vinyl-1-cyclohexene?Introduction 4-Vinyl-1-cyclohexene is an organic compound containing vinyl and cyclohexene groups. The vinyl group in its molecular structure gives it high reactivity, while the cyclohexene group prov..; How to Recycle 4-Vinyl-1-cyclohexene?Background and Overview[1] 4-Vinyl-1-cyclohexene, also known as 4-vinylcyclohexene or p-vinylcyclohexene, is commonly used in photopolymer materials. It is primarily synthesized from butadiene. Recycl..

13. Realated Product Infomation