Cyclohexene oxide

HCID 9246

Basic information

CAS
286-20-4
Standard SMILES
C1CCC2OC2C1
InChIKey
ZWAJLVLEBYIOTI-UHFFFAOYSA-N
Molecular formula
C6H10O
Average molar mass
98.14 g/mol
Monoisotopic mass
98.07316494

Names & identifiers

Preferred name
Cyclohexene oxide
IUPAC
7-oxabicyclo[4.1.0]heptane
English name
Cyclohexene oxide
Molecular formula
C6H10O
Molecular weight
98.14

Names & synonyms

Cyclohexene oxide7-Oxabicyclo[4.1.0]heptane286-20-41,2-EPOXYCYCLOHEXANECyclohexene epoxideTetramethyleneoxiraneCyclohexylene oxideCyclohexene 1-oxideCyclohexane, 1,2-epoxy-Cyclohexane oxide1,2-Cyclohexene oxideCCHO
Show more names
EPOXYCYCLOHEXANE1,2-epoxy-cyclohexan(1R,6S)-7-Oxabicyclo[4.1.0]heptaneHXOohexene oxide7-OxanorcaraneCyclohexenoxide
DTXSID6024880Cyclohexene, oxideCyclohexene-1-oxide7-Oxabicyclo(4.1.0)heptaneDTXCID404880NSC-5218NSC-128074RefChem:129656

Database identifiers

CAS
286-20-4
PubChem CID
9246
DTXSID
DTXSID6024880
ChEMBL
CHEMBL1361659
EC Number
206-007-7
Nikkaji
J2.980G

Properties

Computed structural properties

XLogP
1.2
Topological polar surface area
12.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
7

Experimental & physicochemical properties

OdorSTRONG ODOR
Density0.967 @ 25 °C/4 °C
Color/FormCOLORLESS LIQUID
Solubility · 2 items

SOL IN ALC, ETHER, ACETONE; INSOL IN WATER

VERY SOL IN BENZENE; SOL IN CHLOROFORM

Flash Point81 °C CC
Boiling Point129-130 °C

Physicochemical properties

Melting point
-40 °C · -40 °C
Boiling point
129 · 129-130 °C(lit.)
Density
0.97 g/mL · 0.97 g/mL at 25 °C(lit.)
vapor pressure
12 hPa · 12 hPa (20 °C)
refractive index
20 · n20/D 1.452(lit.)
Flash point
81 °F · 81 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 3.2% (5 of 158) of reports.

Danger

H226 (95.6%): Flammable liquid and vapor [Warning Flammable liquids];H302 (96.2%): Harmful if swallowed [Warning Acute toxicity, oral];H311 (84.8%): Toxic in contact with skin [Danger Acute toxicity, dermal];H312 (20.9%): Harmful in contact with skin [Warning Acute toxicity, dermal];H314 (77.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];H318 (58.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H331 (72.2%): Toxic if inhaled [Danger Acute toxicity, inhalation];H341 (52.5%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

P203, P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P361+P364, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 158 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 5 of 158 reports by companies.;There are 15 notifications provided by 153 of 158 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 3 items

Chemical: 7-Oxabicyclo[4.1.0]heptane

Status: Active Update: 20-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5629

Epoxycyclohexane: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialFLAMMABLE, DANGEROUS FIRE RISK.
Hazards SummaryA tumorigen and mutagen; [RTECS] An irritant; [MSDSonline]
Peroxide Forming Chemical · 4 items

Cyclohexene Oxide

D*: Other compounds that may form peroxides

1 samples had 1 ppm peroxide; age >1 yrs

Management of time-sensitive chemicals (JCHAS)

Hazard Classes and Categories · 2 items

Flam. Liq. 3 (95.6%);Acute Tox. 4 (96.2%);Acute Tox. 3 (84.8%);Acute Tox. 4 (20.9%);Skin Corr. 1B (77.8%);Eye Dam. 1 (58.9%);Acute Tox. 3 (72.2%);Muta. 2 (52.5%)

Flammable liquids - Category 3;Acute toxicity (Oral) - Category 4;Acute toxicity (Dermal) - Category 3

Toxicology

Interactions · 4 items

MODIFIER OF MICROSOMAL EPOXIDE HYDRASE ACTIVITY, CYCLOHEXENE OXIDE, EXERTS DIFFERENTIAL EFFECTS ON CATALYTIC ACTIVITY OF PURIFIED ENZYME FROM RAT LIVER. CYCLOHEXENE OXIDE INHIBITS RATE OF METAB OF BENZO(A)PYRENE 11,12-OXIDE & DIBENZO(A,H)-ANTHRACENE 5,6-OXIDE.

CYCLOHEXENE OXIDE ADMIN IP TO RATS, INHIBITED BILIARY EXCRETION OF METHYL MERCURY. THESE RESULTS PROBABLY REFLECT THE CONJUGATION OF CYCLOHEXENE TO GLUTATHIONE IN THE LIVER.

CO-ADMIN OF CYCLOHEXANE OXIDE AND CHLOROBENZENE REDUCED THE RATE OF METABOLISM OF CHLOROBENZENE AND PREVENTED HEPATIC CENTRILOBULAR NECROSIS CAUSED BY THIS COMPD IN RATS.

INDUCED LUNG HYDROXYLASES HAD KM VALUES OF 1.10 AND 0.52 IN MOUSE AND HAMSTER, RESPECTIVELY. THEY WERE STRONGLY STIMULATED BY CYCLOHEXENE OXIDE.

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=286-20-4]

Human Toxicity ExcerptsCYCLOHEXENE OXIDE IS A CILIA TOXIC AND MUCUS COAGULATING AGENT IDENTIFIED IN AIR POLLUTANTS. /FROM TABLE/
Non-Human Toxicity Excerpts · 4 items

MUTAGENICITY: MUTATION RESEARCH 87: 17 (1981). SISTER CHROMATID EXCHANGE - IN VITRO CHROMOSOMAL EFFECT STUDIES, NON-HUMAN: QUESTIONABLE.

CYCLOHEXANE OXIDE WAS INVESTIGATED USING AMES SALMONELLA TYPHIMURIUM ASSAY WITHOUT ADDN OF LIVER HOMOGENATE FRACTIONS. IT IS FOUND TO BE A WEAK MUTAGEN FOR TA100 & TA1535 STRAINS.

12 EPOXIDE COMPD WERE TESTED FOR CARCINOGENIC ACTIVITY IN RATS AFTER SC INJECTION @ MAX TOLERATED DOSES WITHOUT TOXIC OR ULCERATIVE EFFECTS. 1,2-EPOXYCYCLOHEXANE WAS INACTIVE.

CYCLOHEXENE OXIDE EXERTED DIFFERENTIAL EFFECTS ON NUCLEAR AND MICROSOMAL EPOXIDE HYDRASE WHICH WERE DEPENDENT ON SUBSTRATE AND ON THE ORGANELLE.

Toxicity DataLCLo (rat) = 2,000 ppm/4h

Regulatory information

Regulatory Information · 3 items

Chemical: 7-Oxabicyclo[4.1.0]heptane

Status: Active Update: 20-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5629

Epoxycyclohexane: Does not have an individual approval but may be used under an appropriate group standard

Safety data

PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
rtecs
RN7175000
ridadr
UN 2924 3/PG 3
hs_code
29109000

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

RABBIT LIVER MICROSOMES OXIDIZED CYCLOHEXENE OXIDE. THEREFORE, EPOXIDES ARE INTERMEDIATES IN THE OXIDATION OF ALKENES TO GLYCOLS IN LIVER MICROSOMES.

ON INCUBATION WITH RABBIT LIVER MICROSOMES CYCLOHEXENE OXIDE WAS CONVERTED TO THE CORRESPONDING 1,2-GLYCOL BY EPOXIDE HYDRASE.

Uses & manufacturing

Uses · 3 items

Used as a chemical intermediate for epoxy resins and photoreactive polymers; [HSDB]

CHEMICAL INTERMEDIATE

CHEM INT, EG, FOR EPOXY RESINS & PHOTOREACTIVE POLYMERS

U.S. Exports · 2 items

(1979) No Data

(1981) No Data

U.S. Imports · 2 items

(1979) 6.26X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1981) No Data

U.S. Production · 2 items

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Methods of ManufacturingPROBABLY BY REACTION OF CYCLOHEXENE WITH A PEROXY ACID, EG, PERACETIC ACID
Formulations/PreparationsGRADE: 98% PURE.
Applications · 2 items

UsesCyclohexene oxide has been patented for use as an insecticidal fumigant. Cyclohexene oxide is an important intermediate in the organic industry. It is employed in the manufacture of medicines, pesticides, dyes, and perfumes. In addition, cyclohexene oxide can be used as a monomer in polymerization, chain-cutting agent, flame retardant and diluting agent among other uses. Cyclohexene oxide is useful as a monomer in polymerization with CO2 for production of cyclic carbonates and polycarbonates in the presence of different catalysts.

UsesIt is an important raw material and intermediate used in organic synthesis, dyestuffs and in agrochemical industries. It is used in medicine. Cyclohexene oxide (epoxycyclohexane) is an useful monomer in polymerization and coating industry. It is used in the synthesis of alicyclic target materials including pharmaceuticals, perfumery and dyestuffs. It is used as a monomer in photopolymerizations, with carbonmonoxide to yield aromatic polycarbonates which has minimum impurities.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
山东旭晨化工科技有限公司0533-15715337262 15715337262 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]

Related reactions

171 records

Compound notes

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