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Epoxycyclohexan

Cyclohexene oxide

HCID 9246
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Grundinformationen

CAS
286-20-4
Standard-SMILES
C1CCC2OC2C1
InChIKey
ZWAJLVLEBYIOTI-UHFFFAOYSA-N
Summenformel
C6H10O
Durchschnittliche Molmasse
98,14 g/mol
Monoisotopische Masse
98,07316494

Überblick

inhibitor of epoxide hydrase; structure

Namen und Bezeichner

Bevorzugter Name
Cyclohexene oxide
IUPAC
7-oxabicyclo[4.1.0]heptane
Lokaler Name
Epoxycyclohexan
Englischer Name
Cyclohexene oxide
Summenformel
C6H10O
Molmasse
98.14

Namen und Synonyme

Cyclohexene oxide286-20-47-Oxabicyclo[4.1.0]heptane1,2-EPOXYCYCLOHEXANECyclohexene epoxideTetramethyleneoxiraneCyclohexylene oxideCyclohexene 1-oxideCyclohexane oxideCyclohexane, 1,2-epoxy-1,2-Cyclohexene oxideCCHO
Weitere Namen anzeigen
EPOXYCYCLOHEXANE1,2-epoxy-cyclohexan(1R,6S)-7-Oxabicyclo[4.1.0]heptaneHXOohexene oxide7-OxanorcaraneCyclohexenoxide
Cyclohexene-1-oxideDTXSID60248807-Oxabicyclo(4.1.0)heptaneCyclohexene, oxideDTXCID404880NSC-5218NSC-1280741XYE04C550

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,2
Polarare Oberfläche (TPSA)
12,5 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
7
Formalladung
0
Komplexität
70,2

Experimentelle und physikochemische Eigenschaften

PolymersPlastics & Rubber -> Epoxides
SpringerMaterials PropertiesChemical shift
OdorSTRONG ODOR
Density0.967 @ 25 °C/4 °C
Color/FormCOLORLESS LIQUID
Solubility · 2 Einträge

SOL IN ALC, ETHER, ACETONE; INSOL IN WATER

VERY SOL IN BENZENE; SOL IN CHLOROFORM

Flash Point81 °C CC
Boiling Point129-130 °C
Melting PointGREATER THAN -10 °C
Refractive IndexINDEX OF REFRACTION: 1.4503 @ 25 °C/D
Physical DescriptionColorless liquid; [HSDB]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

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]

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.

Danger

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: 7-Oxabicyclo[4.1.0]heptane

REACH registered substance: 1,2-epoxycyclohexane (EC: 206-007-7)

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 Einträge

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 Einträge

Flam. Liq. 3 (95.6%)

Flammable liquids - Category 3

Toxikologische Informationen

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

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.

Verwendung und Herstellung

Uses · 3 Einträge

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 Einträge

(1979) No Data

(1981) No Data

U.S. Imports · 2 Einträge

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

(1981) No Data

U.S. Production · 2 Einträge

(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.
General Manufacturing Information7-Oxabicyclo[4.1.0]heptane: ACTIVE
Anwendungen · 1 Eintrag

VerwendenCyclohexene 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.

Zugehörige Reaktionen

171
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 26248
HRID 26248als Eduktuspto-grants-1979_04
Reaktionsgleichung von HRID 36477
HRID 36477als Eduktuspto-grants-1995_05
Reaktionsgleichung von HRID 73616
HRID 73616als Eduktuspto-grants-2014_09
Reaktionsgleichung von HRID 95203
HRID 95203als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 99751
HRID 99751als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 129099
HRID 129099als Eduktuspto-grants-1995_11
Reaktionsgleichung von HRID 135852
HRID 135852als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 153908
HRID 153908als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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Physikochemische Eigenschaften

Schmelzpunkt
40 °C · ca. −40 °C
Siedepunkt
130 °C · ca. 130 °C
Dichte
0.97 g·cm−3 · 0.97 g·cm−3
Dampfdruck
12 hPa · 12 hPa (20 °C)
Brechungsindex
1.45 · 1.45
Flammpunkt
27 °C · 27 °C
storage temp.
30 °C · Store below +30°C.
Aggregatzustand
liquid
Farbe
Colorless
Explosionsgrenze
1.2 · 1.2-6.5%(V)
Wasserlöslichkeit
INSOLUBLE
BRN
383568 · 383568
InChI
1S/C6H10O/c1-2-4-6-5(3-1)7-6/h5-6H,1-4H2
InChIKey
ZWAJLVLEBYIOTI-UHFFFAOYSA-N
SMILES
C1CCC2OC2C1
CAS Datenbank
286 · 286-20-4(CAS DataBase Reference)
NIST chemische Informationen
Cyclohexene oxide(286-20-4)
EPA chemische Informationen
Cyclohexene oxide (286-20-4)
Interactions · 4 Einträge

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 Eintrag

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 Einträge

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

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 2924 3/PG 3
hs_code
29109000
RTECS-Nr.
RN7175000
risk_code
10-20/21/22-34
Toxizität
LD50 orally in Rabbit: 1060 mg/kg LD50 dermal Rabbit 612 mg/kg
hazard_code
C
safety_code
26-36/37/39-45-16
hazard_class
8
packing_group
II
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
286-20-4(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 4 OralEye Dam. 1Flam. Liq. 3Muta. 2Skin Corr. 1B
Selbstentzündungstemperatur
703 °F

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

DibortrioxidTrimethylstibinCyclohexenWasserstoffperoxidBis(2-methoxyethyl)ether1,4-DioxanHexacarbonylwolframCyclohex-2-en-1-olCyclohexan

Nachgelagerte Produkte

Propargite E.C.2-(4-tert-Butylphenoxy)cyclohexyl-prop-2-ynyl-sulfit2-(4-tert-Butylphenoxy)cyclohexanolIodcyclohexanCyclohexan-1,2-diol1,2,3,4-tetrahydro-PhenazineCyclopentanmethanol2-(3-Methoxyphenyl)cyclohexanonAdipaldehydtrans-1,2-Dichlorcyclohexantrans-1,2-Dibromcyclohexan1,3-dioxepan-2-one