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4-Chloro-3-nitrobenzenesulfonamide

PubChem CID
7324
Structure
4-Chloro-3-nitrobenzenesulfonamide_small.png
4-Chloro-3-nitrobenzenesulfonamide_3D_Structure.png
Molecular Formula
Synonyms
  • 4-CHLORO-3-NITROBENZENESULFONAMIDE
  • 97-09-6
  • 3-Nitro-4-chlorobenzenesulfonamide
  • Benzenesulfonamide, 4-chloro-3-nitro-
  • 4-chloro-3-nitrobenzene-1-sulfonamide
Molecular Weight
236.63 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-25

1 Structures

1.1 2D Structure

Chemical Structure Depiction
4-Chloro-3-nitrobenzenesulfonamide.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-chloro-3-nitrobenzenesulfonamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C6H5ClN2O4S/c7-5-2-1-4(14(8,12)13)3-6(5)9(10)11/h1-3H,(H2,8,12,13)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C1=CC(=C(C=C1S(=O)(=O)N)[N+](=O)[O-])Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C6H5ClN2O4S
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 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 Nikkaji Number

2.3.7 NSC Number

2.3.8 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
236.63 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
0.8
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
5
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
235.9658555 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
235.9658555 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
114 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
14
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
320
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; [MSDSonline]

3.2.2 Vapor Pressure

0.0000018 [mmHg]

3.2.3 LogP

log Kow = 0.66
Sangster J; LogKow Databank. A Databank of Evaluated Octanol- Water Partition Coefficients on microcomputer diskette. Montreal, Quebec Canada. Sangster Research Labs (1994)

3.3 Chemical Classes

Nitrogen Compounds -> Other Aromatics (Nitrogen)

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 5
View All
NIST Number
75925
Library
Main library
Total Peaks
116
m/z Top Peak
30
m/z 2nd Highest
236
m/z 3rd Highest
64
Thumbnail
Thumbnail
2 of 5
View All
NIST Number
256522
Library
Replicate library
Total Peaks
120
m/z Top Peak
75
m/z 2nd Highest
74
m/z 3rd Highest
64
Thumbnail
Thumbnail

4.3 IR Spectra

4.3.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
S. Somasekhara, Sarabhai Chemicals, Baroda, India
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Use and Manufacturing

7.1 Uses

Sources/Uses
Used as a chemical intermediate for azo dyes; [HSDB]
CHEMICAL INTERMEDIATE FOR AZO DYES
SRI
Dye intermediate
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V8 174 (1979)

7.2 Methods of Manufacturing

POSSIBLY BY REACTION OF 4-CHLORO-3-NITROBENZENESULFONYLCHLORIDE WITH AQUEOUS AMMONIA
SRI

7.3 U.S. Production

(1972) 2.3X10+8 GRAMS
SRI
(1975) 7.90X10+7 GRAMS
SRI
(1976) 3.16X10+5 kg
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V8 174 (1979)

7.4 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzenesulfonamide, 4-chloro-3-nitro-: INACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (96.6%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (96.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (96.6%): 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 59 reports by companies from 6 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 (96.6%)

Eye Irrit. 2A (96.6%)

STOT SE 3 (96.6%)

8.1.3 Hazards Summary

Used therapeutically, sulfonamides can cause a range of hypersensitivity reactions including rashes and injury to the liver and kidneys; Methemoglobinemia has been reported after overdose; [HSDB] An irritant; May cause skin sensitization; [MSDSonline]

8.2 Accidental Release Measures

8.2.1 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

8.3 Regulatory Information

REACH Registered Substance

9 Toxicity

9.1 Toxicological Information

9.1.1 Adverse Effects

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Methemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

9.2 Ecological Information

9.2.1 Environmental Fate / Exposure Summary

4-Chloro-3-nitrobenzenesulfonamide's production and use as a dye intermediate may result in its release to the environment through various waste streams. If released to soil, 4-chloro-3-nitrobenzenesulfonamide should have very high mobility. Volatilization of 4-chloro-3-nitrobenzenesulfonamide should not be important from moist or dry soil surfaces. Insufficient data are available to determine the rate or importance of biodegradation of 4-chloro-3-nitrobenzenesulfonamide in soil or water. If released to water, 4-chloro-3-nitrobenzenesulfonamide should not adsorb to suspended solids and sediment. 4-Chloro-3-nitrobenzenesulfonamide would be essentially non-volatile from water surfaces. An estimated BCF value of 1.9 suggests that 4-chloro-3-nitrobenzenesulfonamide will not bioconcentrate in aquatic organisms. If released to the atmosphere, 4-chloro-3-nitrobenzenesulfonamide will exist as both a vapor and particulate. Vapor-phase 4-chloro-3-nitrobenzenesulfonamide is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 438 days. Particulate-phase 4-chloro-3-nitrobenzenesulfonamide may be physically removed from the air by wet and dry deposition. (SRC)

9.2.2 Artificial Pollution Sources

4-Chloro-3-nitrobenzenesulfonamide's production and use as a dye intermediate(1) may result in its release to the environment through various waste streams(SRC).
(1) Bannister DW et al; Kirk-Othmer Encyclopedia of Chemical Technology 3rd ed NY,NY: John Wiley and Sons Vol 8: 159-212 (1979)

9.2.3 Environmental Fate

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 54(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that 4-chloro-3-nitrobenzenesulfonamide should have very high mobility in soil(SRC). Volatilization of 4-chloro-3-nitrobenzenesulfonamide should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 1.8X10-6 mm Hg(5,SRC). Insufficient data are available to determine the rate or importance of biodegradation of 4-chloro-3-nitrobenzenesulfonamide in soil(SRC).
(1) Swann RL et al; Res Rev 85: 23 (1983)
(2) Sangster J; LogKow Databank. A Databank of Evaluated Octanol-Water Partition Coefficients on microcomputer diskette. Montreal, Quebec Canada. Sangster Research Labs (1994)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 4-9 (1990)
(4) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(5) Lyman WJ; p 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE (eds), Boca Raton, FL: CRC Press (1985)
AQUATIC FATE: An estimated Koc value of 54(SRC), determined from an experimental log Kow(1) and a recommended regression-derived equation(2), indicates that 4-chloro-3-nitrobenzenesulfonamide should not adsorb to suspended solids and sediment(SRC) in the water(2,SRC). 4-Chloro-3-nitrobenzenesulfonamide would be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). An estimated BCF value of 1.9(2,SRC), from an experimental log Kow(1), suggests that 4-chloro-3-nitrobenzenesulfonamide will not bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(4). Insufficient data are available to determine the rate or importance of biodegradation of 4-chloro-3-nitrobenzenesulfonamide in water(SRC).
(1) Sangster J; LogKow Databank. A Databank of Evaluated Octanol-Water Partition Coefficients on microcomputer diskette. Montreal, Quebec Canada. Sangster Research Labs (1994)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 4-9, 5-4, 5-10, 15-1 to 15-29 (1990)
(3) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(4) Franke C et al; Chemosphere 29: 1501-14 (1994)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-chloro-3-nitrobenzenesulfonamide, which has an estimated vapor pressure of 1.8X10-6 mm Hg at 25 °C(2,SRC) will exist as both a vapor and particulate in the ambient atmosphere. Vapor-phase 4-chloro-3-nitrobenzenesulfonamide is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 438 days(3,SRC). Particulate-phase 4-chloro-3-nitrobenzenesulfonamide may be physically removed from the air by wet and dry deposition(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE (eds), Boca Raton, FL: CRC Press (1985)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)

9.2.4 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of 4-chloro-3-nitrobenzenesulfonamide with photochemically produced hydroxyl radicals has been estimated as 3.8X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 438 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)

9.2.5 Environmental Bioconcentration

An estimated BCF value of 1.9 was calculated for 4-chloro-3-nitrobenzenesulfonamide(SRC), using an experimental log Kow of 0.66(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will not be an important fate process(SRC).
(1) Sangster J; LogKow Databank. A Databank of Evaluated Octanol-Water Partition Coefficients on microcomputer diskette. Montreal, Quebec Canada. Sangster Research Labs (1994)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 5-4, 5-10 (1990)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

9.2.6 Soil Adsorption / Mobility

The Koc of 4-chloro-3-nitrobenzenesulfonamide is estimated as approximately 54(SRC), using an experimental log Kow of 0.66(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 4-chloro-3-nitrobenzenesulfonamide should have very high mobility in soil(SRC).
(1) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 4-9 (1990)
(3) Swann RL et al; Res Rev 85: 23 (1983)

9.2.7 Volatilization from Water / Soil

The Henry's Law constant for 4-chloro-3-nitrobenzenesulfonamide is estimated as 1.2X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 4-chloro-3-nitrobenzenesulfonamide will be essentially nonvolatile from water surfaces(2,SRC). 4-Chloro-3-nitrobenzenesulfonamide's vapor pressure, 1.8X10-6 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry or moist soil should not occur(SRC).
(1) Meylan WM, Howard PH; Environ Toxicol Chem 10: 1283-93 (1991)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Lyman WJ; p 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE (eds), Boca Raton, FL: CRC Press (1985)

10 Literature

10.1 Consolidated References

10.2 Springer Nature References

10.3 Thieme References

10.4 Wiley References

10.5 Chemical Co-Occurrences in Literature

10.6 Chemical-Gene Co-Occurrences in Literature

10.7 Chemical-Disease 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 ChEMBL Target Tree

13.3 UN GHS Classification

13.4 NORMAN Suspect List Exchange Classification

13.5 EPA DSSTox Classification

13.6 EPA TSCA and CDR Classification

13.7 EPA Substance Registry Services Tree

13.8 MolGenie Organic Chemistry Ontology

14 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
    Benzenesulfonamide, 4-chloro-3-nitro-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    4-Chloro-3-nitrobenzenesulphonamide
    https://comptox.epa.gov/dashboard/DTXSID8052649
    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
    4-chloro-3-nitrobenzenesulphonamide
    https://chem.echa.europa.eu/100.002.328
  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. Hazardous Substances Data Bank (HSDB)
    4-CHLORO-3-NITROBENZENESULFONAMIDE
    https://pubchem.ncbi.nlm.nih.gov/source/hsdb/2568
  9. 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
  10. 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
    4-Chloro-3-nitrobenzenesulfonamide
    https://haz-map.com/Agents/3287
  11. Japan Chemical Substance Dictionary (Nikkaji)
  12. 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
    Benzenesulfonamide, 4-chloro-3-nitro-
    http://www.nist.gov/srd/nist1a.cfm
  13. SpectraBase
    Benzenesulfonamide, 4-chloro-3-nitro-
    https://spectrabase.com/spectrum/DxdWdlv9QEQ
    Benzenesulfonamide, 4-chloro-3-nitro-
    https://spectrabase.com/spectrum/IFPMMmkIX3i
    4-CHLORO-3-NITROBENZENESULFONAMIDE
    https://spectrabase.com/spectrum/K8wzLAiMheU
    4-chloro-3-nitrobenzenesulfonamide
    https://spectrabase.com/spectrum/EkhouXLPGon
    4-CHLORO-3-NITROBENZENESULFONAMIDE
    https://spectrabase.com/spectrum/9nhSUPJPj10
  14. Springer Nature
  15. 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/
  16. Wikidata
    4-chloro-3-nitrobenzenesulfonamide
    https://www.wikidata.org/wiki/Q27255164
  17. Wiley
  18. PubChem
  19. GHS Classification (UNECE)
  20. 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/
  21. EPA Substance Registry Services
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  23. PATENTSCOPE (WIPO)
CONTENTS