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4-((2-Hydroxy-1-naphthyl)azo)benzenesulphonic acid

PubChem CID
11315
Structure
4-((2-Hydroxy-1-naphthyl)azo)benzenesulphonic acid_small.png
4-((2-Hydroxy-1-naphthyl)azo)benzenesulphonic acid_3D_Structure.png
Molecular Formula
Synonyms
  • 573-89-7
  • Acid orange ii
  • 4-((2-Hydroxy-1-naphthyl)azo)benzenesulphonic acid
  • Mandarin G
  • Tropaeolin OOO
Molecular Weight
328.3 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11
Description
4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid is a member of naphthols.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
4-((2-Hydroxy-1-naphthyl)azo)benzenesulphonic acid.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[(2-hydroxynaphthalen-1-yl)diazenyl]benzenesulfonic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C16H12N2O4S/c19-15-10-5-11-3-1-2-4-14(11)16(15)18-17-12-6-8-13(9-7-12)23(20,21)22/h1-10,19H,(H,20,21,22)
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

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

2.1.4 SMILES

C1=CC=C2C(=C1)C=CC(=C2N=NC3=CC=C(C=C3)S(=O)(=O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C16H12N2O4S
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 Nikkaji Number

2.3.7 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

Acid Orange II

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
328.3 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
2.9
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
328.05177804 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
328.05177804 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
108 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
23
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
523
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 Dissociation Constants

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

1 of 4
View All
Authors
Krauss M, Schymanski EL, Weidauer C, Schupke H, UFZ and Eawag
Instrument
Q Exactive Plus Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
35 (nominal)
Fragmentation Mode
HCD
Column Name
Kinetex C18 EVO 2.6 um, 2.1x50 mm, precolumn 2.1x5 mm, Phenomenex
Retention Time
13.403 min
Precursor m/z
329.0591
Precursor Adduct
[M+H]+
Top 5 Peaks

329.0593 999

156.0444 890

128.0495 819

173.0142 480

312.0565 328

Thumbnail
Thumbnail
License
CC BY
Reference
Schymanski, E. L.; Ruttkies, C.; Krauss, M.; Brouard, C.; Kind, T.; Dührkop, K.; Allen, F.; Vaniya, A.; Verdegem, D.; Böcker, S.; et al. Critical Assessment of Small Molecule Identification 2016: Automated Methods. Journal of Cheminformatics 2017, 9 (1). DOI:10.1186/s13321-017-0207-1
2 of 4
View All
Authors
Krauss M, Schymanski EL, Weidauer C, Schupke H, UFZ and Eawag
Instrument
Q Exactive Plus Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
35 (nominal)
Fragmentation Mode
HCD
Column Name
Kinetex C18 EVO 2.6 um, 2.1x50 mm, precolumn 2.1x5 mm, Phenomenex
Retention Time
13.232 min
Precursor m/z
327.0445
Precursor Adduct
[M-H]-
Top 5 Peaks

327.0444 999

170.9995 693

155.9886 167

93.0331 112

107.0365 75

Thumbnail
Thumbnail
License
CC BY
Reference
Schymanski, E. L.; Ruttkies, C.; Krauss, M.; Brouard, C.; Kind, T.; Dührkop, K.; Allen, F.; Vaniya, A.; Verdegem, D.; Böcker, S.; et al. Critical Assessment of Small Molecule Identification 2016: Automated Methods. Journal of Cheminformatics 2017, 9 (1). DOI:10.1186/s13321-017-0207-1

6 Chemical Vendors

7 Safety and Hazards

7.1 Hazards Identification

7.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports. Pictograms displayed are for < 0.1% (0 of 2) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

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

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

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

There are 0 notifications provided by 0 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.

7.1.2 Hazard Classes and Categories

Not Classified

8 Literature

8.1 Consolidated References

8.2 NLM Curated PubMed Citations

8.3 Springer Nature References

8.4 Chemical Co-Occurrences in Literature

8.5 Chemical-Gene Co-Occurrences in Literature

8.6 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 ChEBI Ontology

10.3 ChemIDplus

10.4 UN GHS Classification

10.5 NORMAN Suspect List Exchange Classification

10.6 EPA DSSTox Classification

10.7 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
    4-[(2-hydroxy-1-naphthyl)azo]benzenesulphonic acid
    https://echa.europa.eu/substance-information/-/substanceinfo/100.008.512
    4-[(2-hydroxy-1-naphthyl)azo]benzenesulphonic acid (EC: 209-362-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/126093
  5. ChEBI
    4-[(2-Hydroxy-1-naphthalenyl)azo]benzenesulfonic acid
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:179961
  6. 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
  7. IUPAC Digitized pKa Dataset
    benzenesulfonic acid, 4-(2-hydroxynaphth-1-ylazo)-
    https://github.com/IUPAC/Dissociation-Constants
  8. Japan Chemical Substance Dictionary (Nikkaji)
  9. MassBank Europe
  10. 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
  11. Springer Nature
  12. Wikidata
  13. PubChem
  14. 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
  15. GHS Classification (UNECE)
  16. 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/
  17. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  18. PATENTSCOPE (WIPO)
CONTENTS