An official website of the United States government

Phenylmethylsulfonyl Fluoride

PubChem CID
4784
Structure
Phenylmethylsulfonyl Fluoride_small.png
Phenylmethylsulfonyl Fluoride_3D_Structure.png
Phenylmethylsulfonyl Fluoride__Crystal_Structure.png
Molecular Formula
Synonyms
  • Phenylmethylsulfonyl fluoride
  • PMSF
  • 329-98-6
  • phenylmethanesulfonyl fluoride
  • Benzenemethanesulfonyl fluoride
Molecular Weight
174.19 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-02-01
Description
Phenylmethanesulfonyl fluoride is an acyl fluoride with phenylmethanesulfonyl as the acyl group. It has a role as a serine proteinase inhibitor. It is functionally related to a phenylmethanesulfonic acid.
Phenylmethylsulfonyl fluoride has been reported in Ixora coccinea with data available.
An enzyme inhibitor that inactivates IRC-50 arvin, subtilisin, and the fatty acid synthetase complex.
See also: 4-Toluenesulfonyl fluoride (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Phenylmethylsulfonyl Fluoride.png

1.2 3D Conformer

1.3 Crystal Structures

CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

phenylmethanesulfonyl fluoride
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C7H7FO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

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

2.1.4 SMILES

C1=CC=C(C=C1)CS(=O)(=O)F
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C7H7FO2S
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 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 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 NSC Number

2.3.12 Wikidata

2.3.13 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Benzenemethanesulfonyl Fluoride
  • Fluoride, Benzenemethanesulfonyl
  • Fluoride, Phenylmethanesulfonyl
  • Fluoride, Phenylmethylsulfonyl
  • Phenylmethanesulfonyl Fluoride
  • Phenylmethylsulfonyl Fluoride

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
174.19 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3
Property Value
1.3
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
174.01507880 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
174.01507880 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
42.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
199
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 Physical Description

Colorless solid; [Merck Index] White crystals; [Sigma-Aldrich MSDS]

3.3 Chemical Classes

Other Uses -> Biochemical Research

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
BRUKER AC-300
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1991-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Varian A-60D
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Eastman Organic Chemicals, Rochester, New York
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
Thumbnail

4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 4
View All
NIST Number
233923
Library
Main library
Total Peaks
47
m/z Top Peak
91
m/z 2nd Highest
174
m/z 3rd Highest
65
Thumbnail
Thumbnail
2 of 4
View All
NIST Number
73418
Library
Replicate library
Total Peaks
33
m/z Top Peak
91
m/z 2nd Highest
65
m/z 3rd Highest
174
Thumbnail
Thumbnail

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
EASTMAN ORGANIC CHEMICALS, ROCHESTER, NEW YORK
Catalog Number
9432
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
KBr0
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Spectrochem Pvt. Ltd.
Catalog Number
11687
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
MP Biomedicals
Catalog Number
195381
Lot Number
9911F
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Sigma-Aldrich Company Llc
Catalog Number
<a href=https://www.sigmaaldrich.com/US/en/product/sigma/P7626>P7626</a>
Lot Number
063K0079
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories
Source of Sample
Spectrochem Pvt. Ltd., India
Catalog Number
11687
Copyright
Copyright © 2014-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
MP Biomedicals, LLC.
Catalog Number
195381
Lot Number
9911F
Copyright
Copyright © 2013-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Enzyme Inhibitors
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)
Protease Inhibitors
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)

9 Use and Manufacturing

9.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
A serine and cysteine protease inhibitor; Used as a protease inhibitor in research and to prevent proteolytic degradation in protein purification; [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.

9.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzenemethanesulfonyl fluoride: ACTIVE

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Corrosive
Acute Toxic
Signal
Danger
GHS Hazard Statements

H301 (99%): Toxic if swallowed [Danger Acute toxicity, oral]

H314 (99%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statement Codes

P260, P264, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, 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 103 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.

10.1.2 Hazard Classes and Categories

Acute Tox. 3 (99%)

Skin Corr. 1B (99%)

10.1.3 Hazards Summary

Causes convulsions and multiple enzyme effects in acute intraperitoneal studies of mice; [RTECS] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Toxic by ingestion; Targets the nerves, heart, blood, and eyes; [Sigma-Aldrich MSDS] See Methanesulfonyl fluoride.

10.2 Exposure Control and Personal Protection

Exposure Summary
Biological Exposure Indices (BEI) [ACGIH] - Fluorides in urine = 2 mg/L prior to shift or 3 mg/L at end of shift; (Repeated measurements recommended.)
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.
Maximum Allowable Concentration (MAK)
1.0 [mg/m3], inhalable fraction, as F[German Research Foundation (DFG)]

10.2.1 Permissible Exposure Limit (PEL)

2.5 [mg/m3], as F

10.2.2 Threshold Limit Values (TLV)

2.5 [mg/m3], as F

10.3 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Phenylmethanesulphonyl fluoride: Does not have an individual approval but may be used under an appropriate group standard

11 Toxicity

11.1 Toxicological Information

11.1.1 Adverse Effects

Dermatotoxin - Skin burns.

Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

11.1.2 Acute Effects

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Nature Journal References

13.7 Chemical Co-Occurrences in Literature

13.8 Chemical-Gene Co-Occurrences in Literature

13.9 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.2 Chemical-Target Interactions

15.3 Pathways

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 ChemIDplus

18.4 ChEMBL Target Tree

18.5 UN GHS Classification

18.6 EPA CPDat Classification

18.7 NORMAN Suspect List Exchange Classification

18.8 EPA DSSTox Classification

18.9 EPA TSCA and CDR Classification

18.10 LOTUS Tree

18.11 PFAS and Fluorinated Organic Compounds in PubChem

18.12 EPA Substance Registry Services Tree

18.13 MolGenie Organic Chemistry Ontology

19 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
    Benzenemethanesulfonyl fluoride
    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. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    Phenylmethylsulfonyl fluoride
    https://www.wikidata.org/wiki/Q411575
  11. 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
  12. 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
  13. Therapeutic Target Database (TTD)
  14. EPA Chemical and Products Database (CPDat)
  15. 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
    Phenylmethylsulfonyl fluoride
    https://haz-map.com/Agents/16574
  16. FooDB
    LICENSE
    FooDB 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 (FooDB) and the original publication.
    https://foodb.ca/about
  17. 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
    Phenylmethylsulfonyl fluoride
    http://www.hmdb.ca/metabolites/HMDB0256652
  18. Japan Chemical Substance Dictionary (Nikkaji)
  19. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  20. Natural Product Activity and Species Source (NPASS)
  21. Metabolomics Workbench
  22. Nature Chemical Biology
  23. Nature Chemistry
  24. 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
    Benzenemethanesulfonyl fluoride
    http://www.nist.gov/srd/nist1a.cfm
  25. SpectraBase
    Benzenemethanesulfonyl fluoride
    https://spectrabase.com/spectrum/Kis6Omdo2ev
    Benzenemethanesulfonyl fluoride
    https://spectrabase.com/spectrum/4xfpvD1i309
    alpha-TOLUENESULFONYL FLUORIDE
    https://spectrabase.com/spectrum/KfTc28DDZ45
    alpha-TOLUENESULFONYL FLUORIDE
    https://spectrabase.com/spectrum/70f1uoPBWFU
    alpha-TOLUENESULFONYL FLUORIDE
    https://spectrabase.com/spectrum/CEzznfpkcUL
    Phenyl methyl sulfonyl fluoride
    https://spectrabase.com/spectrum/3hzSfG8Zdyl
    Phenylmethyl sulfonyl fluoride
    https://spectrabase.com/spectrum/B97ApnDwKaP
    Phenylmethanesulfonyl fluoride
    https://spectrabase.com/spectrum/L4uxUqy5I73
    Phenyl methyl sulfonyl fluoride
    https://spectrabase.com/spectrum/4t0XBoPazFj
    Phenylmethyl sulfonyl fluoride
    https://spectrabase.com/spectrum/A3IDtMPF5hO
  26. NMRShiftDB
  27. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  28. Springer Nature
  29. The Cambridge Structural Database
  30. 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/
  31. Wikidata
    phenylmethanesulfonyl fluoride
    https://www.wikidata.org/wiki/Q411575
  32. Wikipedia
  33. Wiley
  34. 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
    Phenylmethylsulfonyl Fluoride
    https://www.ncbi.nlm.nih.gov/mesh/68010664
  35. PubChem
  36. GHS Classification (UNECE)
  37. 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/
  38. EPA Substance Registry Services
  39. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  40. PATENTSCOPE (WIPO)
  41. NCBI
CONTENTS