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2-(Methoxycarbonyl)benzoic acid

PubChem CID
20392
Structure
2-(Methoxycarbonyl)benzoic acid_small.png
2-(Methoxycarbonyl)benzoic acid_3D_Structure.png
Molecular Formula
Synonyms
  • 2-(Methoxycarbonyl)benzoic acid
  • 4376-18-5
  • Methyl hydrogen phthalate
  • MONOMETHYL PHTHALATE
  • mono-Methyl phthalate
Molecular Weight
180.16 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-04
Description
Monomethyl phthalate is a methyl ester and a phthalic acid monoester.
Monomethyl phthalate is a metabolite, or breakdown product, of dimethyl phthalate, used in insect repellant, plastic, and as a rocket propellant.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2-(Methoxycarbonyl)benzoic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-methoxycarbonylbenzoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C9H8O4/c1-13-9(12)7-5-3-2-4-6(7)8(10)11/h2-5H,1H3,(H,10,11)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

COC(=O)C1=CC=CC=C1C(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C9H8O4
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 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 NSC Number

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 1,2-benzenedicarboxylic acid monomethyl ester
  • monomethyl phthalate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
180.16 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
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
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
180.04225873 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
180.04225873 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
63.6Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
13
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
212
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

Solid

3.2.2 Melting Point

82 - 84 °C

3.2.3 LogP

1.13
HANSCH,C ET AL. (1995)

3.2.4 Collision Cross Section

146.13 Ų [M+Na]+

137.01 Ų [M-H]-

S79 | UACCSCEC | Collision Cross Section (CCS) Library from UAntwerp | DOI:10.5281/zenodo.4704648

3.3 Chemical Classes

Plasticizer metabolites
S79 | UACCSCEC | Collision Cross Section (CCS) Library from UAntwerp | DOI:10.5281/zenodo.4704648

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
317640
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
Frinton Laboratories, South Vineland, New Jersey
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Instrument Name
Jeol PS-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 4
View All
NIST Number
135497
Library
Main library
Total Peaks
60
m/z Top Peak
76
m/z 2nd Highest
104
m/z 3rd Highest
50
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2 of 4
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NIST Number
245779
Library
Replicate library
Total Peaks
50
m/z Top Peak
76
m/z 2nd Highest
104
m/z 3rd Highest
50
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4.2.2 MS-MS

1 of 6
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

149.0233 100

163.0389 57.35

121.0284 7.57

133.0284 5.61

135.044 4.58

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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

149.0233 100

163.0389 47.52

121.0284 34.91

135.044 18.12

133.0284 16.45

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4.2.3 LC-MS

1 of 9
View All
Authors
Belova L, Covaci A, University of Antwerp, Belgium; Caballero-Casero N, University of Cordoba, Spain.
Instrument
Agilent 6560 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
ZORBAX Extend-C18 3.5um, 2.1x50mm, Agilent Technologies
Retention Time
0.332 min
Precursor m/z
179.035
Precursor Adduct
[M-H]-
Top 5 Peaks

77.0389 999

107.0501 110

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License
CC BY
2 of 9
View All
Authors
Belova L, Covaci A, University of Antwerp, Belgium; Caballero-Casero N, University of Cordoba, Spain.
Instrument
Agilent 6560 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
5 eV
Fragmentation Mode
CID
Column Name
ZORBAX Extend-C18 3.5um, 2.1x50mm, Agilent Technologies
Retention Time
0.332 min
Precursor m/z
179.035
Precursor Adduct
[M-H]-
Top 5 Peaks

77.0402 999

107.0496 539

179.0369 273

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License
CC BY

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
CAPILLARY CELL: MELT (CRYSTALLINE PHASE)
Source of Sample
Frinton Laboratories, Inc., South Vineland, New Jersey
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
317640
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
317640
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Use and Manufacturing

7.1 Uses

Monomethyl phthalate is a metabolite, or breakdown product, of dimethyl phthalate, used in insect repellant, plastic, and as a rocket propellant.

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

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

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

H335 (100%): 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 44 reports by companies from 4 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

Skin Irrit. 2 (100%)

Eye Irrit. 2A (100%)

STOT SE 3 (100%)

8.2 Regulatory Information

California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Developmental Toxicity; Endocrine Toxicity; Immunotoxicity; Reproductive Toxicity; Respiratory Toxicity

Authoritative List - CECBP - Priority Chemicals

Report - if used as a fragrance or flavor ingredient

New Zealand EPA Inventory of Chemical Status
1,2-Benzenedicarboxylic acid, monomethyl ester: Does not have an individual approval but may be used under an appropriate group standard

9 Toxicity

9.1 Toxicological Information

9.1.1 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

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 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 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 Protein Bound 3D Structures

13.2 Chemical-Target Interactions

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 UN GHS Classification

16.5 NORMAN Suspect List Exchange Classification

16.6 EPA DSSTox Classification

16.7 EPA Substance Registry Services Tree

16.8 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. California Safe Cosmetics Program (CSCP) Product Database
  2. 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/
  3. 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/
  4. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  5. 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
  6. EPA DSSTox
    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. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  10. ChEBI
  11. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  12. 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
  13. 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
  14. Japan Chemical Substance Dictionary (Nikkaji)
  15. MassBank Europe
  16. 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
  17. Metabolomics Workbench
  18. Natural Product Activity and Species Source (NPASS)
  19. 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
    Methyl hydrogen phthalate
    http://www.nist.gov/srd/nist1a.cfm
  20. SpectraBase
    1,2-Benzenedicarboxylic acid, monomethyl ester
    https://spectrabase.com/spectrum/K6kRy0b4K4p
    Phthalic acid, monomethyl ester
    https://spectrabase.com/spectrum/5NVPVG8C4Ge
    Phthalic acid, monomethyl ester
    https://spectrabase.com/spectrum/55Kbat9RsKD
    Phthalic acid, monomethyl ester
    https://spectrabase.com/spectrum/HdhYnpfhGZJ
  21. NMRShiftDB
  22. 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/
    Mono-methyl phthalate
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  23. Springer Nature
  24. 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/
  25. Wikidata
  26. PubChem
  27. 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
  28. GHS Classification (UNECE)
  29. EPA Substance Registry Services
  30. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  31. PATENTSCOPE (WIPO)
CONTENTS