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Tetramethyl-1,3-cyclobutanedione

PubChem CID
13617
Structure
Tetramethyl-1,3-cyclobutanedione_small.png
Tetramethyl-1,3-cyclobutanedione_3D_Structure.png
Molecular Formula
Synonyms
  • 933-52-8
  • Tetramethyl-1,3-cyclobutanedione
  • Tetramethylcyclobutane-1,3-dione
  • 2,2,4,4-tetramethylcyclobutane-1,3-dione
  • 1,3-Cyclobutanedione, 2,2,4,4-tetramethyl-
Molecular Weight
140.18 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Tetramethyl-1,3-cyclobutanedione.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,2,4,4-tetramethylcyclobutane-1,3-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C8H12O2/c1-7(2)5(9)8(3,4)6(7)10/h1-4H3
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

RGCDVHNITQEYPO-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CC1(C(=O)C(C1=O)(C)C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H12O2
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

933-52-8

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 Nikkaji Number

2.3.7 NSC Number

2.3.8 Wikidata

2.3.9 Wikipedia

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
140.18 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
1.7
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
140.083729621 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
140.083729621 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
34.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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
167
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
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

White crystalline solid; [MSDSonline]

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Other Organic Compounds

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60
Source of Sample
EASTMAN ORGANIC CHEMICALS, ROCHESTER, NEW YORK
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
T21008
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
XL-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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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
227904
Library
Main library
Total Peaks
50
m/z Top Peak
70
m/z 2nd Highest
42
m/z 3rd Highest
41
Thumbnail
Thumbnail
2 of 5
View All
NIST Number
73662
Library
Replicate library
Total Peaks
30
m/z Top Peak
70
m/z 2nd Highest
42
m/z 3rd Highest
41
Thumbnail
Thumbnail

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
EASTMAN ORGANIC CHEMICALS, ROCHESTER, NEW YORK
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
T21008
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

1 of 2
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
D0258
Lot Number
D6KWI-RF
Copyright
Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
T21008
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation 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
D0258
Lot Number
D6KWI-RF
Copyright
Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Use and Manufacturing

7.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
1,3-Cyclobutanedione, 2,2,4,4-tetramethyl-: ACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Note
Pictograms displayed are for 50% (1 of 2) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, 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 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 1 of 2 reports by companies. For more detailed information, please visit ECHA C&L website.

There is 1 notification provided by 1 of 2 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.

8.1.2 Hazard Classes and Categories

Skin Irrit. 2 (50%)

Eye Irrit. 2A (50%)

STOT SE 3 (50%)

8.1.3 Hazards Summary

A tumorigen; [RTECS] May cause irritation; [MSDSonline]

8.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 1,3-Cyclobutanedione, 2,2,4,4-tetramethyl-

9 Toxicity

9.1 Toxicological Information

9.1.1 Non-Human Toxicity Excerpts

AMONG 13 LOW MOLECULAR WEIGHT COMPOUNDS TESTED FOR CARCINOGENIC ACTIVITY BY LIFETIME SC INJECTION IN ICR/HA SWISS MICE, 2,2,4,4-TETRAMETHYL-1,3-CYCLOBUTANEDIONE, CAUSED LOW INCIDENCES OF TUMORS AT THE INJECTION SITE.
VAN DUUREN BL ET AL; CARCINOGENICITY OF ISOSTERS OF EPOXIDES AND LACTONES: AZIRIDINE ETHANOL, PROPANE SULTONE, AND RELATED COMPOUNDS; J NAT CANCER INST 46(1) 143 (1971)

10 Literature

10.1 Consolidated References

10.2 Springer Nature References

10.3 Thieme References

10.4 Chemical Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 ChemIDplus

13.2 UN GHS Classification

13.3 NORMAN Suspect List Exchange Classification

13.4 EPA DSSTox Classification

13.5 EPA TSCA and CDR Classification

13.6 EPA Substance Registry Services Tree

13.7 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    1,3-Cyclobutanedione, 2,2,4,4-tetramethyl-
    https://services.industrialchemicals.gov.au/search-inventory/
  2. 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/
    2,2,4,4-Tetramethyl-1,3-cyclobutanedione
    https://commonchemistry.cas.org/detail?cas_rn=933-52-8
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. 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
  5. EPA Chemicals under the TSCA
    1,3-Cyclobutanedione, 2,2,4,4-tetramethyl-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  6. EPA DSSTox
    2,2,4,4-Tetramethylcyclobutane-1,3-dione
    https://comptox.epa.gov/dashboard/DTXSID4044745
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. 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
  8. 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
  9. Hazardous Substances Data Bank (HSDB)
    2,2,4,4-TETRAMETHYL-1,3-CYCLOBUTANEDIONE
    https://pubchem.ncbi.nlm.nih.gov/source/hsdb/5522
  10. 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
  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
    2,2,4,4-Tetramethyl-1,3-cyclobutanedione
    https://haz-map.com/Agents/2934
  12. Japan Chemical Substance Dictionary (Nikkaji)
  13. 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
    1,3-Cyclobutanedione, 2,2,4,4-tetramethyl-
    http://www.nist.gov/srd/nist1a.cfm
  14. SpectraBase
    2,2,4,4-TETRAMETHYLCYCLOBUTANE-1,3-DIONE
    https://spectrabase.com/spectrum/6gdxFwdYN1P
    1,3-Cyclobutanedione, 2,2,4,4-tetramethyl-
    https://spectrabase.com/spectrum/JlEGGpf3HKR
    2,2,4,4-TETRAMETHYL-1,3-CYCLOBUTANEDIONE
    https://spectrabase.com/spectrum/4mSeeKOvnXU
    1,3-CYCLOBUTANEDIONE, 2,2,4,4-TETRAMETHYL-
    https://spectrabase.com/spectrum/PegI1PUudl
    2,2,4,4-tetramethyl-1,3-cyclobutanedione
    https://spectrabase.com/spectrum/5YZ7Ld56wxN
    Tetramethyl-1,3-cyclobutanedione
    https://spectrabase.com/spectrum/7upIF8b2dOu
    2,2,4,4-TETRAMETHYLCYCLOBUTAN-1,3-DIONE
    https://spectrabase.com/spectrum/KuMnxaQ8Alg
    2,2,4,4-TETRAMETHYL-1,3-CYCLOBUTANEDIONE
    https://spectrabase.com/spectrum/syFledfSa2
    Tetramethyl-1,3-cyclobutanedione
    https://spectrabase.com/spectrum/CSw0cIj9Vaw
    1,3-CYCLOBUTANEDIONE, 2,2,4,4-TETRA- METHYL-,
    https://spectrabase.com/spectrum/L61peLYo6bz
    Tetramethyl-1,3-cyclobutanedione
    https://spectrabase.com/spectrum/1R8dKHOiQCA
    Tetramethyl-1,3-cyclobutanedione
    https://spectrabase.com/spectrum/CyQIgZADXYy
    Tetramethyl-1,3-cyclobutanedione
    https://spectrabase.com/spectrum/G1RFcKZj03y
  15. NMRShiftDB
  16. Springer Nature
  17. SpringerMaterials
  18. 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/
  19. Wikidata
    2,2,4,4-tetramethyl-1,3-cyclobutanedione
    https://www.wikidata.org/wiki/Q27288281
  20. Wikipedia
  21. PubChem
  22. GHS Classification (UNECE)
  23. 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/
  24. EPA Substance Registry Services
  25. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  26. PATENTSCOPE (WIPO)
CONTENTS