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3,4-Diethoxy-3-cyclobutene-1,2-dione

PubChem CID
123228
Structure
3,4-Diethoxy-3-cyclobutene-1,2-dione_small.png
3,4-Diethoxy-3-cyclobutene-1,2-dione_3D_Structure.png
Molecular Formula
Synonyms
  • 3,4-Diethoxy-3-cyclobutene-1,2-dione
  • 5231-87-8
  • Diethyl squarate
  • 3,4-diethoxycyclobut-3-ene-1,2-dione
  • Squaric acid diethyl ester
Molecular Weight
170.16 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-11

1 Structures

1.1 2D Structure

Chemical Structure Depiction
3,4-Diethoxy-3-cyclobutene-1,2-dione.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

3,4-diethoxycyclobut-3-ene-1,2-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C8H10O4/c1-3-11-7-5(9)6(10)8(7)12-4-2/h3-4H2,1-2H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CCOC1=C(C(=O)C1=O)OCC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H10O4
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 DSSTox Substance ID

2.3.4 Nikkaji Number

2.3.5 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • diethoxycyclobutenedione
  • squaric acid diethyl ester

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
170.16 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
0.7
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
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
170.05790880 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
170.05790880 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
52.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
12
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
226
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)

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
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
310778
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
E. V. Dehmlow, R. Zeisberg Org. Magn. Resonance 7, 418(1975)
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 4
View All
NIST Number
156032
Library
Main library
Total Peaks
86
m/z Top Peak
29
m/z 2nd Highest
27
m/z 3rd Highest
31
Thumbnail
Thumbnail
2 of 4
View All
NIST Number
108442
Library
Replicate library
Total Peaks
43
m/z Top Peak
29
m/z 2nd Highest
170
m/z 3rd Highest
113
Thumbnail
Thumbnail

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
CAPILLARY CELL: NEAT
Source of Sample
H. Wamhoff, University of Bonn, Bonn, Germany
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker IFS 85
Technique
Film
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A19248
Lot Number
10189570
Copyright
Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Sample
Aldrich
Catalog Number
310778
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 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
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A19248
Lot Number
10189570
Copyright
Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Safety and Hazards

7.1 Hazards Identification

7.1.1 GHS Classification

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

H301 (19%): Toxic if swallowed [Danger Acute toxicity, oral]

H312 (19%): Harmful in contact with skin [Warning Acute toxicity, dermal]

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

H317 (98.3%): May cause an allergic skin reaction [Warning Sensitization, Skin]

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

H334 (29.3%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

H335 (98.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, 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 58 reports by companies from 8 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.

7.1.2 Hazard Classes and Categories

Acute Tox. 3 (19%)

Acute Tox. 4 (19%)

Skin Irrit. 2 (100%)

Skin Sens. 1 (98.3%)

Eye Irrit. 2A (100%)

Resp. Sens. 1 (29.3%)

STOT SE 3 (98.3%)

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Springer Nature References

8.4 Thieme References

8.5 Chemical Co-Occurrences in Literature

8.6 Chemical-Gene Co-Occurrences in Literature

8.7 Chemical-Disease Co-Occurrences in Literature

9 Patents

9.1 Depositor-Supplied Patent Identifiers

9.2 WIPO PATENTSCOPE

9.3 Chemical Co-Occurrences in Patents

9.4 Chemical-Disease Co-Occurrences in Patents

9.5 Chemical-Gene Co-Occurrences in Patents

10 Classification

10.1 MeSH Tree

10.2 ChemIDplus

10.3 UN GHS Classification

10.4 EPA DSSTox Classification

10.5 MolGenie Organic Chemistry Ontology

11 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. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  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. Japan Chemical Substance Dictionary (Nikkaji)
  6. 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
    3,4-Diethoxy-3-cyclobutene-1,2-dione
    http://www.nist.gov/srd/nist1a.cfm
  7. SpectraBase
    3-CYCLOBUTENE-1,2-DIONE, 3,4-DIETHOXY-
    https://spectrabase.com/spectrum/93dUpZiI9Sz
    3,4-Diethoxy-3-cyclobutene-1,2-dione
    https://spectrabase.com/spectrum/63LnOkYzaiS
    3,4-diethoxy-3-cyclobutene-1,2-dione
    https://spectrabase.com/spectrum/4Rn42kuziKD
    3,4-Diethoxy-3-cyclobutene-1,2-dione
    https://spectrabase.com/spectrum/LWePPylCRkl
    3,4-DIETHOXY-3-CYCLOBUTENE-1,2-DIONE
    https://spectrabase.com/spectrum/EtLic6f99tW
    3,4-Diethoxy-3-cyclobutene-1,2-dione
    https://spectrabase.com/spectrum/jJiG5asOlp
    3,4-Diethoxy-3-cyclobutene-1,2-dione
    https://spectrabase.com/spectrum/GPr0ITKTF5u
    3,4-Diethoxy-3-cyclobutene-1,2-dione
    https://spectrabase.com/spectrum/7L8A5Qw2eTj
    3,4-Diethoxy-3-cyclobutene-1,2-dione
    https://spectrabase.com/spectrum/63dg0WgsCV9
  8. NMRShiftDB
  9. Springer Nature
  10. 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/
  11. Wikidata
  12. PubChem
  13. 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
  14. GHS Classification (UNECE)
  15. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  16. PATENTSCOPE (WIPO)
CONTENTS