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N-(Hydroxymethyl)phthalimide

PubChem CID
8354
Structure
N-(Hydroxymethyl)phthalimide_small.png
N-(Hydroxymethyl)phthalimide_3D_Structure.png
N-(Hydroxymethyl)phthalimide__Crystal_Structure.png
Molecular Formula
Synonyms
  • N-(Hydroxymethyl)phthalimide
  • 118-29-6
  • 2-(hydroxymethyl)isoindoline-1,3-dione
  • N-Hydroxymethylphthalimide
  • Phthalimidomethyl alcohol
Molecular Weight
177.16 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2024-12-27
Description
N-(hydroxymethyl)phthalimide is a primary alcohol comprising phthalimide carrying an N-hydroxymethyl substituent. It is a primary alcohol and a member of phthalimides. It is functionally related to a phthalimide.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-(Hydroxymethyl)phthalimide.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 2
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(hydroxymethyl)isoindole-1,3-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C9H7NO3/c11-5-10-8(12)6-3-1-2-4-7(6)9(10)13/h1-4,11H,5H2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C1=CC=C2C(=C1)C(=O)N(C2=O)CO
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C9H7NO3
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 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 NSC Number

2.3.10 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • N-(hydroxymethyl)phthalimide
  • N-hydroxymethylphthalimide

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
177.16 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.5
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
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
177.042593085 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
177.042593085 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
57.6Ų
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
227
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 Chemical Classes

3.2.1 Pesticides

Environmental transformation -> Pesticide transformation products (metabolite, successor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

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.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
H41803
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
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2 of 2
Instrument Name
Bruker WP-80
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 5
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NIST Number
235306
Library
Main library
Total Peaks
77
m/z Top Peak
147
m/z 2nd Highest
104
m/z 3rd Highest
76
Thumbnail
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2 of 5
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NIST Number
271934
Library
Replicate library
Total Peaks
84
m/z Top Peak
76
m/z 2nd Highest
50
m/z 3rd Highest
147
Thumbnail
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4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Stauffer Chemical Company, Anderson Chemical Division
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
KBr WAFER
Source of Sample
Frinton Laboratories, Inc., South Vineland, New Jersey
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.3.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
H41803
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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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
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6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Transformations

PIMOH (N-Hydroxymethyl phthalimide acid is a known environmental transformation product of Phosmet.
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

8 Pharmacology and Biochemistry

8.1 Transformations

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Environmental transformation -> Pesticide transformation products (metabolite, successor)
S60 | SWISSPEST19 | Swiss Pesticides and Metabolites from Kiefer et al 2019 | DOI:10.5281/zenodo.3544759

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 88.1% (37 of 42) of all reports. Pictograms displayed are for 11.9% (5 of 42) of reports that indicate hazard statements.
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (11.9%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (11.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (11.9%): 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 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 37 of 42 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 2 notifications provided by 5 of 42 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

Skin Irrit. 2 (11.9%)

Eye Irrit. 2A (11.9%)

STOT SE 3 (11.9%)

10.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-: Does not have an individual approval but may be used under an appropriate group standard

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 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 MeSH Tree

14.2 ChEBI Ontology

14.3 ChemIDplus

14.4 UN GHS Classification

14.5 NORMAN Suspect List Exchange Classification

14.6 EPA DSSTox Classification

14.7 EPA TSCA and CDR Classification

14.8 EPA Substance Registry Services Tree

14.9 MolGenie Organic Chemistry Ontology

15 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
    1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    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. 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/
  9. ChEBI
  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. 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/
  12. The Cambridge Structural Database
  13. Japan Chemical Substance Dictionary (Nikkaji)
  14. Metabolomics Workbench
  15. 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
    1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-
    http://www.nist.gov/srd/nist1a.cfm
  16. SpectraBase
    1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-
    https://spectrabase.com/spectrum/6opCJCCXCAq
    1H-Isoindole-1,3(2H)-dione, 2-(hydroxymethyl)-
    https://spectrabase.com/spectrum/51zofYBKoI7
    2-ISOINDOLINEMETHANOL, 1,3-DIOXO-,
    https://spectrabase.com/spectrum/3UPlvuu8yBq
  17. NMRShiftDB
  18. 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/
  19. Springer Nature
  20. 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/
  21. Wikidata
    N-hydroxymethylphthalimide
    https://www.wikidata.org/wiki/Q27117985
  22. PubChem
  23. 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
  24. GHS Classification (UNECE)
  25. EPA Substance Registry Services
  26. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  27. PATENTSCOPE (WIPO)
CONTENTS