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Cyclohexene oxide

PubChem CID
637978
Structure
Cyclohexene oxide_small.png
Cyclohexene oxide_3D_Structure.png
Molecular Formula
Synonyms
  • Cyclohexane oxide
  • Cyclohexene-1-oxide
  • 2,3-tetramethyleneoxirane
  • UNII-1XYE04C550
  • CCRIS 1227
Molecular Weight
98.14 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-01-25
  • Modify:
    2025-02-01

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cyclohexene oxide.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,6S)-7-oxabicyclo[4.1.0]heptane
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C6H10O/c1-2-4-6-5(3-1)7-6/h5-6H,1-4H2/t5-,6+
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

ZWAJLVLEBYIOTI-OLQVQODUSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1CC[C@H]2[C@@H](C1)O2
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C6H10O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

286-20-4

2.3.2 Deprecated CAS

137422-07-2, 26637-95-6, 28165-18-6

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 Nikkaji Number

2.3.6 Wikidata

2.3.7 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

cyclohexene oxide

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
98.14 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
98.073164938 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
98.073164938 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
12.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
7
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
70.2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Colorless liquid; [HSDB]

3.2.2 Color / Form

COLORLESS LIQUID
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 248

3.2.3 Odor

STRONG ODOR
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 248

3.2.4 Boiling Point

129-130 °C
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 248

3.2.5 Melting Point

GREATER THAN -10 °C
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-261

3.2.6 Flash Point

81 °C CC
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 248

3.2.7 Solubility

SOL IN ALC, ETHER, ACETONE; INSOL IN WATER
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 248
VERY SOL IN BENZENE; SOL IN CHLOROFORM
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-261

3.2.8 Density

0.967 @ 25 °C/4 °C
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 248

3.2.9 Refractive Index

INDEX OF REFRACTION: 1.4503 @ 25 °C/D
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 248

3.3 SpringerMaterials Properties

3.4 Chemical Classes

3.4.1 Polymers

Plastics & Rubber -> Epoxides

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
NMR: 6228 (Sadtler Research Laboratories Spectral Collection)
2 of 2
1D NMR Spectra

4.1.1 13C NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
JEOL JMS-DX-300
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

41 99.99

70 83.52

57 68.38

98 58.63

81 56.49

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Thumbnail
License
CC BY-NC-SA

4.2.2 Other MS

Other MS
MASS: 225 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)

4.3 IR Spectra

IR Spectra
IR: 3449 (Sadtler Research Laboratories Prism Collection)

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

RABBIT LIVER MICROSOMES OXIDIZED CYCLOHEXENE OXIDE. THEREFORE, EPOXIDES ARE INTERMEDIATES IN THE OXIDATION OF ALKENES TO GLYCOLS IN LIVER MICROSOMES.
LEIBMAN KC; ORTIZ E; J PHARMACOL EXP THER 173(2) 242 (1970)
ON INCUBATION WITH RABBIT LIVER MICROSOMES CYCLOHEXENE OXIDE WAS CONVERTED TO THE CORRESPONDING 1,2-GLYCOL BY EPOXIDE HYDRASE.
JERINA D ET AL; ARCH BIOCHEM BIOPHYS 128(1) 176 (1968)

8 Use and Manufacturing

8.1 Uses

Sources/Uses
Used as a chemical intermediate for epoxy resins and photoreactive polymers; [HSDB]
CHEMICAL INTERMEDIATE
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 248
CHEM INT, EG, FOR EPOXY RESINS & PHOTOREACTIVE POLYMERS
SRI

8.2 Methods of Manufacturing

PROBABLY BY REACTION OF CYCLOHEXENE WITH A PEROXY ACID, EG, PERACETIC ACID
SRI

8.3 Formulations / Preparations

GRADE: 98% PURE.
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 248

8.4 U.S. Production

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS
SRI
(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS
SRI

8.5 U.S. Imports

(1979) 6.26X10+7 GRAMS (PRINCPL CUSTMS DISTS)
SRI
(1981) No Data
SRI

8.6 U.S. Exports

(1979) No Data
SRI
(1981) No Data
SRI

8.7 General Manufacturing Information

EPA TSCA Commercial Activity Status

9 Identification

9.1 Analytic Laboratory Methods

EPOXIDES WERE REACTED WITH AN EXCESS AMT OF 4-(P-NITROBENZYL)PYRIDINE AND THE ABSORBANCE OF THE PRODUCT AT ABSORBANCE MAX WAS MEASURED FOR THE DETERMINATION OF THE CONCN OF EPOXIDES.
AGARWAL SC ET AL; BULL ENVIRON CONTAM TOXICOL 23(6) 825 (1979)

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 2
View All
Note
Pictograms displayed are for 96.8% (153 of 158) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 3.2% (5 of 158) of reports.
Pictogram(s)
Flammable
Corrosive
Acute Toxic
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H226 (95.6%): Flammable liquid and vapor [Warning Flammable liquids]

H302 (96.2%): Harmful if swallowed [Warning Acute toxicity, oral]

H311 (91.8%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H312 (13.9%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H314 (84.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H318 (51.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H331 (79.1%): Toxic if inhaled [Danger Acute toxicity, inhalation]

H341 (45.6%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

Precautionary Statement Codes

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

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

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. For more detailed information, please visit ECHA C&L website.

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.

10.1.2 Hazard Classes and Categories

Flam. Liq. 3 (95.6%)

Acute Tox. 4 (96.2%)

Acute Tox. 3 (91.8%)

Acute Tox. 4 (13.9%)

Skin Corr. 1B (84.8%)

Eye Dam. 1 (51.9%)

Acute Tox. 3 (79.1%)

Muta. 2 (45.6%)

Flammable liquids - Category 3

Acute toxicity (Oral) - Category 4

Acute toxicity (Dermal) - Category 3

10.1.3 Hazards Summary

A tumorigen and mutagen; [RTECS] An irritant; [MSDSonline]

10.1.4 Fire Potential

FLAMMABLE, DANGEROUS FIRE RISK.
Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 248

10.2 Stability and Reactivity

10.2.1 Peroxide Forming Chemical

Chemical
Cyclohexene Oxide
Class (* = UMN Designation)
D*: Other compounds that may form peroxides
Peroxide Concentration Over Time

10.3 Regulatory Information

The Australian Inventory of Industrial Chemicals
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Epoxycyclohexane: Does not have an individual approval but may be used under an appropriate group standard

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

11.1.2 Toxicity Data

LCLo (rat) = 2,000 ppm/4h

11.1.3 Interactions

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.
LEVIN W ET AL; MOL PHARMACOL 14(6) 1107 (1978) (RECD 1979)
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.
REFSVIK T; ACTA PHARMACOL TOXICOL 42(2) 135 (1978)
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.
OESCH F ET AL; CHEM -BIOL INTERACTIONS 6(3) 189 (1973)
INDUCED LUNG HYDROXYLASES HAD KM VALUES OF 1.10 AND 0.52 IN MOUSE AND HAMSTER, RESPECTIVELY. THEY WERE STRONGLY STIMULATED BY CYCLOHEXENE OXIDE.
HILL DL, SHIH T; INHIBITION OF BENZO(A)PYRENE METABOLISM CATALYZED BY MOUSE AND HAMSTER LUNG MICROSOMES; CANCER RES 35(10) 2717 (1975)

11.1.4 Human Toxicity Excerpts

CYCLOHEXENE OXIDE IS A CILIA TOXIC AND MUCUS COAGULATING AGENT IDENTIFIED IN AIR POLLUTANTS. /FROM TABLE/
Searle, C. E. (ed.). Chemical Carcinogens. ACS Monograph 173. Washington, DC: American Chemical Society, 1976., p. 339

11.1.5 Non-Human Toxicity Excerpts

MUTAGENICITY: MUTATION RESEARCH 87: 17 (1981). SISTER CHROMATID EXCHANGE - IN VITRO CHROMOSOMAL EFFECT STUDIES, NON-HUMAN: QUESTIONABLE.
GENE-TOX Program: Current Status of Bioassay in Genetic Toxicology. U.S. Environmental Protection Agency, Washington, DC. Office of Toxic Substances and Pesticides. (For program information, contact Environmental Mutagen Information Center, Oak Ridge National Laboratory, Post Office Box Y, Oak Ridge, Tennessee 37830. Telephone (615) 574-7871)
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.
FRANTZ SW ET AL; MUTAT RES 90(1) 67 (1981)
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.
VAN-DUUREN BL ET AL; J NATL CANCE INST 39(6) 1213 (1967)
CYCLOHEXENE OXIDE EXERTED DIFFERENTIAL EFFECTS ON NUCLEAR AND MICROSOMAL EPOXIDE HYDRASE WHICH WERE DEPENDENT ON SUBSTRATE AND ON THE ORGANELLE.
BORNSTEIN WA ET AL; COMPARISON OF NUCLEAR & MICROSOMAL EPOXIDE HYDRASE FROM RAT LIVER; ARCH BIOCHEM BIOPHYS 197(2) 436 (1979)

11.1.6 Ongoing Test Status

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]

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Thieme References

12.4 Wiley References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 ChemIDplus

16.3 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemicals under the TSCA
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Hazardous Substances Data Bank (HSDB)
  7. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  8. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  9. NITE-CMC
    Cyclohexene oxide - FY2011 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/11-mhlw-0165e.html
  10. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  11. NMRShiftDB
  12. Japan Chemical Substance Dictionary (Nikkaji)
  13. Lab and Research Safety, University of Minnesota
    Cyclohexene Oxide
  14. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  15. Protein Data Bank in Europe (PDBe)
  16. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  17. SpectraBase
  18. SpringerMaterials
  19. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  20. Wikidata
  21. Wikipedia
  22. Wiley
  23. PubChem
  24. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  25. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  26. PATENTSCOPE (WIPO)
CONTENTS