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2,5-Dimethyl-1,4-benzoquinone

PubChem CID
8718
Structure
2,5-Dimethyl-1,4-benzoquinone_small.png
2,5-Dimethyl-1,4-benzoquinone_3D_Structure.png
Molecular Formula
Synonyms
  • 2,5-Dimethyl-1,4-benzoquinone
  • 137-18-8
  • p-Xyloquinone
  • Phlorone
  • 2,5-Dimethyl-p-benzoquinone
Molecular Weight
136.15 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-04
Description
2,5-Dimethyl-1,4-benzoquinone has been reported in Perithalia capillaris with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2,5-Dimethyl-1,4-benzoquinone.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

2,5-dimethylcyclohexa-2,5-diene-1,4-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C8H8O2/c1-5-3-8(10)6(2)4-7(5)9/h3-4H,1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

MYKLQMNSFPAPLZ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=CC(=O)C(=CC1=O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H8O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 Metabolomics Workbench ID

2.3.7 Nikkaji Number

2.3.8 NSC Number

2.3.9 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 2,5-dimethyl-1,4-benzoquinone
  • 2,5-dimethyl-4-benzoquinone
  • 2,5-dimethyl-p-benzoquinone
  • 2,5-dimethylquinone

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
136.15 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.3
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
2
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
136.052429494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
136.052429494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
34.1Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
228
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
0
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

Yellow solid; [Acros Organics MSDS]

3.2.2 Vapor Pressure

0.02 [mmHg]

3.2.3 Kovats Retention Index

Semi-standard non-polar
1129, 1129

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Aromatic Ketones

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian A-60
Source of Sample
H. M. van DORT, ALGEMENE KUNSTZIJDE UNIE N.V., ARNHEM, THE NETHERLANDS
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
H. Van Dort, Algemene Kunstzijde De Unie N.V., Arnhem, the Netherlands
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.1.3 17O 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

1 of 5
View All
NIST Number
231805
Library
Main library
Total Peaks
80
m/z Top Peak
136
m/z 2nd Highest
68
m/z 3rd Highest
39
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2 of 5
View All
NIST Number
134191
Library
Replicate library
Total Peaks
68
m/z Top Peak
39
m/z 2nd Highest
136
m/z 3rd Highest
68
Thumbnail
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4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
H. M. van DORT, ALGEMENE KUNSTZIJDE UNIE N.V., ARNHEM, THE NETHERLANDS
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
KBr1
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
D0686
Lot Number
YFZ5H-FQ
Copyright
Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.2 ATR-IR Spectra

Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
D0686
Lot Number
YFZ5H-FQ
Copyright
Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.3 Vapor Phase IR Spectra

Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 Raman Spectra

Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
D0686
Lot Number
YFZ5H-FQ
Copyright
Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Use and Manufacturing

7.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
2,5-Cyclohexadiene-1,4-dione, 2,5-dimethyl-: INACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Irritant
Signal
Danger
GHS Hazard Statements

H301 (97.5%): Toxic if swallowed [Danger Acute toxicity, oral]

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (97.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, 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 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

8.1.2 Hazard Classes and Categories

Acute Tox. 3 (97.5%)

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

STOT SE 3 (97.5%)

8.1.3 Hazards Summary

Causes somnolence and convulsions in oral, intraperitoneal, and subcutaneous lethal-dose studies of mice; Oral LD50 (mouse) = 290 mg/kg; [RTECS] An irritant; [Acros Organics MSDS] See Quinone.

9 Toxicity

9.1 Toxicological Information

9.1.1 Acute Effects

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Nature Journal References

11.6 Chemical Co-Occurrences in Literature

11.7 Chemical-Gene Co-Occurrences in Literature

11.8 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

16 Classification

16.1 MeSH Tree

16.2 ChemIDplus

16.3 ChEMBL Target Tree

16.4 UN GHS Classification

16.5 NORMAN Suspect List Exchange Classification

16.6 EPA DSSTox Classification

16.7 EPA TSCA and CDR Classification

16.8 LOTUS Tree

16.9 EPA Substance Registry Services Tree

16.10 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  4. EPA Chemicals under the TSCA
    2,5-Cyclohexadiene-1,4-dione, 2,5-dimethyl-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    2,5-Cyclohexadiene-1,4-dione, 2,5-dimethyl-
    https://comptox.epa.gov/dashboard/DTXSID0059669
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. 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
  7. 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
  8. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  9. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  10. 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/
  11. 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
    2,5-Dimethyl-4-benzoquinone
    https://haz-map.com/Agents/19495
  12. Japan Chemical Substance Dictionary (Nikkaji)
  13. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    2,5-Dimethyl-1,4-benzoquinone
    https://www.wikidata.org/wiki/Q81988919
  14. Natural Product Activity and Species Source (NPASS)
  15. Metabolomics Workbench
  16. Nature Chemical Biology
  17. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    2,5-Cyclohexadiene-1,4-dione, 2,5-dimethyl-
    http://www.nist.gov/srd/nist1a.cfm
  18. SpectraBase
    2,5-Cyclohexadiene-1,4-dione, 2,5-dimethyl-
    https://spectrabase.com/spectrum/8Hqc8nqCWv2
    2,5-Cyclohexadiene-1,4-dione, 2,5-dimethyl-
    https://spectrabase.com/spectrum/C4eXcmElqBJ
    P-BENZOQUINONE, 2,5-DIMETHYL-,
    https://spectrabase.com/spectrum/2HJOLQPeyMp
  19. NMRShiftDB
  20. Springer Nature
  21. SpringerMaterials
  22. 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/
  23. Wikidata
    2,5-Cyclohexadiene-1,4-dione, 2,5-dimethyl-
    https://www.wikidata.org/wiki/Q81988919
  24. PubChem
  25. 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
  26. GHS Classification (UNECE)
  27. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  28. EPA Substance Registry Services
  29. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  30. PATENTSCOPE (WIPO)
CONTENTS