Vinyl cyclohexene dioxide

HCID 7833CAS 106-87-6

Basic information

Standard SMILES
C1CC2OC2CC1C1CO1
InChIKey
OECTYKWYRCHAKR-UHFFFAOYSA-N
Molecular formula
C8H12O2
Average molar mass
140.18 g/mol
Monoisotopic mass
140.08372962

Names & identifiers

Preferred name
Vinyl cyclohexene dioxide
IUPAC
3-(oxiran-2-yl)-7-oxabicyclo[4.1.0]heptane
English name
4-Vinylcyclohexene dioxide
Molecular formula
C8H12O2
Molecular weight
140.18

Names & synonyms

4-Vinylcyclohexene dioxide106-87-64-Vinyl-1-cyclohexene dioxide3-(oxiran-2-yl)-7-oxabicyclo[4.1.0]heptane4-Vinylcyclohexene diepoxide4-Vinyl-1-cyclohexene diepoxideVINYLCYCLOHEXENE DIOXIDEVinyl cyclohexene dioxideVinyl cyclohexene diepoxide1-Vinyl-3-cyclohexene dioxideChissonox 2061-Ethyleneoxy-3,4-epoxycyclohexane
Show more names
VCD7-oxabicyclo[4.1.0]heptane,3-oxiranyl-VCHDep-206ERL 4206
7-Oxabicyclo[4.1.0]heptane, 3-oxiranyl-1-Epoxyethyl-3,4-epoxycyclohexaneUnox epoxide 2064-Vinyl-1,2-cyclohexene diepoxideChissonox 206 monomerVinylcyclohexene DiepoxideErla-2270Erla-2271

Database identifiers

CAS
106-87-6、25086-25-3
PubChem CID
7833
DTXSID
DTXSID0020604
ChEMBL
CHEMBL1734307
ChEBI
CHEBI:59001
UNII
596C064IG4
EC Number
203-437-7
Nikkaji
J65.676C

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
25.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
10

Experimental & physicochemical properties

LogP1.3
Density · 6 items

1.0986 at 68 °F (NTP, 1992) - Denser than water; will sink

1.0986 @ 20 °C/20 °C

Relative density (water = 1): 1.10

1.099

1.0966 @ 20°C

1.10

Viscosity7.77 CP @ 20 °C
Color/Form · 2 items

COLORLESS LIQUID

Colorless liquid.

Solubility · 4 items

50 to 100 mg/mL at 72 °F (NTP, 1992)

SOL IN WATER

Solubility in water, g/100ml at 20 °C: 18.3

High

Flash Point · 5 items

230 °F (NTP, 1992)

230 °F

110 °C o.c.

230 °F (open cup)

(oc) 230 °F

Physicochemical properties

Melting point
-55 °C · -55°C
Boiling point
230 · 230-232 °C(lit.)
Density
1.094 g/mL · 1.094 g/mL at 25 °C(lit.)
refractive index
20 · n20/D 1.477(lit.)
Flash point
225 °F · 225 °F
storage temp.
2 · under inert gas (nitrogen or Argon) at 2-8°C

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral];H331: Toxic if inhaled [Danger Acute toxicity, inhalation];H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity];H350: May cause cancer [Danger Carcinogenicity];H360F: May damage fertility [Danger Reproductive toxicity]

P203, P261, P264, P270, P271, P280, P301+P317, P304+P340, P316, P318, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

Hazard information

Regulatory Information · 4 items

Chemical: 7-Oxabicyclo[4.1.0]heptane, 3-oxiranyl-

Hazard Traits - Carcinogenicity; Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B; IARC Carcinogens - 2B; NTP RoC - reasonable; Prop 65;Report - regardless of intended function of ingredient in the product

Vinyl cyclohexene dioxide: HSNO Approval: HSR003101 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Epoxidised cycloaliphatic olefins: Human health tier II assessment;IMAP assessments - 7-Oxabicyclo[4.1.0]heptane, 3-oxiranyl-: Environment tier I assessment
DOT LabelPoison
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible. Risk of fire and explosion on contact with acids or bases.

Fire PotentialSlight, when exposed to heat or flame.
Health Hazards · 1 item

Excerpt from NIOSH Pocket Guide for Vinyl cyclohexene dioxide:;Exposure Routes: Inhalation, skin absorption, ingestion, skin and/or eye contact;Symptoms: In Animals: irritation eyes, skin, respiratory system; testicular atrophy; leukopenia (reduced blood leukocytes), necrosis thymus; skin sensitization; [potential occupational carcinogen];Target Organs: Eyes, skin, respiratory system, blood, thymus, reproductive system;Cancer Site: [in animals: skin tumors] (NIOSH, 2024)

Safety & protection

Fire Fighting · 2 items

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

First Aid · 2 items

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital.;OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Water wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and wash the skin with water. If symptoms occur after washing, get medical attention immediately.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe StorageSeparated from food and feedstuffs, alcohols, amines and other active hydrogen compounds. Dry. Ventilation along the floor.
Fire Fighting ProceduresTo fight fire: Water, foam, dry chemical.
Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and protect it from moisture. (NTP, 1992)

Toxicology

Cancer Sites[in animals: skin tumors]
Target OrgansEyes, skin, respiratory system, blood, thymus, reproductive system
Adverse Effects · 1 item

Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.;Skin Sensitizer - An agent that can induce an allergic reaction in the skin.;Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.;IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.;NTP Carcinogen - Reasonably anticipated to be a human carcinogen.;ACGIH Carcinogen - Confirmed Animal.

Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Signs and Symptoms · 5 items

Cough. Laboured breathing. Sore throat.

MAY BE ABSORBED! Dry skin. Redness. Pain. Swelling.

Redness. Pain.

See Inhalation.

In Animals: irritation eyes, skin, respiratory system; testicular atrophy; leukopenia (reduced blood leukocytes), necrosis thymus; skin sensitization; [potential occupational carcinogen]

Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=106-87-6]

Regulatory information

Regulatory Information · 4 items

Chemical: 7-Oxabicyclo[4.1.0]heptane, 3-oxiranyl-

Hazard Traits - Carcinogenicity; Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B; IARC Carcinogens - 2B; NTP RoC - reasonable; Prop 65;Report - regardless of intended function of ingredient in the product

Vinyl cyclohexene dioxide: HSNO Approval: HSR003101 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

TSCA RequirementsSection 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.

Safety data

OEB
A
OEL
TWA: 10 ppm (60 mg/m3) [skin]
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
RN8640000

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 4 items

In vitro studies with rabbit liver microsomal preparations showed that 4-vinyl-1-cyclohexene diepoxide can be metabolized to monoepoxymonoglycols, 1,2-hydroxy-4-vinylcyclohexane oxide, and 4-(1',2'-dihydroxyethyl)-1-cyclohexane oxide. Formation of these products is catalyzed by epoxide hydrolase. Conjugation with glutathione is another pathway for metabolism of 4-vinyl-1- cyclohexene. Depletion of reduced glutathione /was reported/ in the liver of mice given ip injections of 500 mg/kg 4-vinyl-1-cyclohexene diepoxide.

Carcinogenicity studies have shown that chronic administration of 4-vinylcyclohexene will induce ovarian tumors in B6C3F1 mice but not F-344 rats. This occurs because the blood level of the ovotoxic 4-vinylcyclohexene metabolite, 4-vinylcyclohexene-1,2-epoxide, is dramatically higher in 4-vinylcyclohexene treated female mice compared with rats. This species difference in 4-vinylcyclohexene epoxidation is also reflected in the rate of 4-vinylcyclohexene metabolism by hepatic microsomes (female mouse greater than female rat). The present study assessed the ability of microsomes obtained from human liver to metabolize 4-vinylcyclohexene to epoxides since humans are exposed to 4-vinylcyclohexene in certain occupational settings. The production of 4-vinylcyclohexene-1,2-epoxide and 4-vinylcyclohexene-7,8-epoxide from 4-vinylcyclohexene (1 mM) by human hepatic microsomes was linear with respect to microsomal protein concentration (0.25-1.0 mg/ml) and incubation time (5-20 min). 4-Vinylcyclohexene-1,2-epoxide was the major metabolite, while the rate 4-vinylcyclohexene-7,8-epoxide formation was about 6 fold lower and in some cases was below the limit of detection. There was no dramatic difference in the rate of 4-vinylcyclohexene epoxidation by hepatic microsomes obtained from male and female humans. The rate of 4-vinylcyclohexene-1,2-epoxide formation by female human hepatic microsomes was 0.71 + or - 0.35 nmol/mg microsomal protein/min (n = 4). This is 13 and 2 fold lower than the rate of 4-vinylcyclohexene-1,2-epoxide formation by female mouse and rat hepatic microsomes, respectively.

4-Vinylcyclohexene is a chemical to which humans are exposed in the rubber industry. A chronic carcinogenicity bioassay conducted by the NTP showed that oral administration of 4-vinylcyclohexene induced tumors in the ovaries of mice but not in those of rats. The hypothesis tested was that the species and organ specificity of 4-vinylcyclohexene toxicity was due to differences in the disposition of 4-vinylcyclohexene between the female rat and mouse. Therefore, the disposition of a single oral dose of 400 mg/kg (14)C 4-vinylcyclohexene was studied in female B6C3F1 mice and Fischer 344 rats. Mice eliminated greater than 95% of the dose in 24 hr, whereas rats required 48 hr to eliminate greater than 95% of the dose. The major routes of excretion of (14)C 4-vinylcyclohexene derived radioactivity were in the urine (50-60%) and expired air (30-40%). No evidence was obtained to indicate that the ovaries of either species retained 4-vinylcyclohexene as a parent cmpd or as radioactive equivalents. A dramatic difference was observed between the rat and mouse in the appearance of a monoepoxide of 4-vinylcyclohexene in blood from 0.5 to 6 hr after 4-vinylcyclohexene administration (800 mg/kg, ip). 4-Vinylcyclohexene-1,2-epoxide was present in the blood of mice with the highest concentration at 2 hr (41 nmol/ml). The blood concentration of 4-vinylcyclohexene-1,2-epoxide in rats was less than 2.5 nmol/ml at all times examined. 4-Vinylcyclohexene-7,8-epoxide was not present in the blood of either species at the level of detection. These findings were supported by in vitro studies of 4-vinylcyclohexene epoxidation by liver microsomes. The rate of epoxidation of 4-vinylcyclohexene (1 mM) to 4-vinylcyclohexene-1,2-epoxide was 6.5 fold greater in mouse liver microsomes than that in rat liver microsomes. The species difference in the rate of epoxide formation by the liver may be an important factor in the species difference in susceptibility to 4-vinylcyclohexene induced ovarian tumors.

VCH-diepoxide is a known human metabolite of 1,2-Epoxy-4-vinylcyclohexane and Epoxy-4-vinylcyclohexene.

MeSH Pharmacological ClassificationSubstances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Absorption, Distribution and Excretion · 1 item

4-Vinyl-1-cyclohexene diepoxide is absorbed by rodents exposed dermally orally, or by inhalation. ... Rats and mice received 0.1 ml and 0.01 ml, respectively, of dose mixtures containing 500 mg/ml (200 uc/ml) [ethylene-(14)C] 4-vinyl-1-cyclohexene diepoxide in acetone. The preliminary results indicate that 30% of the dose applied to the skin is absorbed over a 24 hr period for both rats and mice; only 1%-3% of the dose remained on the skin at the site of application. By 24 hr, 70%-80% of the absorbed dose had been eliminated from the body, virtually all in the urine. The radioactivity remaining in the body was distributed over a number of tissues, with no tissue containing more than 1% of the applied dose. The liver, muscle, and adipose tissue, however, contained 0.5%-1.6% and 1.2%-2.9% of the absorbed dose in rat and mouse tissue, respectively. Tissue to blood ratios ranged from 0.3 to 1.5 in rats and from 0.8 to 2.8 in mice.

Uses & manufacturing

Uses · 4 items

Used in the plastics industry to manufacture polymers and other organic chemicals; [ACGIH]

POLYMERS; ORGANIC SYNTHESIS

CHEM INT FOR CONDENSATION WITH DICARBOXYLIC ACIDS.

... IS USED AS REACTIVE DILUENT FOR OTHER DIEPOXIDES & FOR EPOXY RESINS DERIVED FROM BISPHENOL-A & EPICHLOROHYDRIN.

Methods of ManufacturingONE GRADE OF 1-EPOXYETHYL-3,4-EPOXYCYCLOHEXENE AVAIL IN US HAS EPOXY EQUIV OF 74-78. ... CAN BE PREPARED BY PERACETIC ACID EPOXIDIZATION OF 4-VINYLCYCLOHEXANE.
General Manufacturing Information · 2 items

7-Oxabicyclo[4.1.0]heptane, 3-(2-oxiranyl)-: ACTIVE

IT HAS BEEN PROPOSED FOR USE AS CHEM INTERMEDIATE (EG, FOR CONDENSATION WITH DICARBOXYLIC ACIDS) & AS MONOMER (EG, FOR PREPN OF POLYGLYCOLS CONTAINING UNREACTED EPOXY GROUPS OR FOR HOMO-POLYMERIZATION TO 3-DIMENSIONAL RESIN).

Applications · 4 items

UsesAs a chemical intermediate and as a reactive diluent for diepoxides and epoxy resins.

UsesVinylcyclohexene dioxide (VCD) may be used to study and understand its effect on ovarian follicles and effects on epithelial differentiation.

UsesVinylcyclohexene 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.

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

Suppliers50 total

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Additional notes

DefinitionChEBI: The diepoxide of 4-vinylcyclohexene.

Related reactions

3 records

Linked notes

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