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Methyl 4-bromocrotonate

PubChem CID
5369175
Structure
Methyl 4-bromocrotonate_small.png
Methyl 4-bromocrotonate_3D_Structure.png
Molecular Formula
Synonyms
  • Methyl 4-bromocrotonate
  • 1117-71-1
  • 6000-00-6
  • (E)-Methyl 4-bromobut-2-enoate
  • 4-Bromocrotonic Acid Methyl Ester
Molecular Weight
179.01 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2024-12-28

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Methyl 4-bromocrotonate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl (E)-4-bromobut-2-enoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C5H7BrO2/c1-8-5(7)3-2-4-6/h2-3H,4H2,1H3/b3-2+
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RWIKCBHOVNDESJ-NSCUHMNNSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COC(=O)/C=C/CBr
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C5H7BrO2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

1117-71-1

2.3.2 European Community (EC) Number

2.3.3 ChEMBL ID

2.3.4 DSSTox Substance ID

2.3.5 Nikkaji Number

2.3.6 NSC Number

2.3.7 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
179.01 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
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
177.96294 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
177.96294 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
26.3Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
8
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
98.6
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
1
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 liquid; [Alfa Aesar MSDS]

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Halogenated Esters

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 17O NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 6
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NIST Number
71214
Library
Main library
Total Peaks
95
m/z Top Peak
99
m/z 2nd Highest
39
m/z 3rd Highest
68
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2 of 6
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NIST Number
235390
Library
Main library
Total Peaks
121
m/z Top Peak
99
m/z 2nd Highest
39
m/z 3rd Highest
68
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4.3 IR Spectra

4.3.1 FTIR Spectra

Technique
Neat
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
M32100
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
M32100
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.3.3 Vapor Phase IR Spectra

Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
M32100
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Use and Manufacturing

7.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
2-Butenoic acid, 4-bromo-, methyl ester: ACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

H314 (15.2%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H315 (84.8%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (89.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H335 (84.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P332+P317, P362+P364, P363, 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 46 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 Corr. 1B (15.2%)

Skin Irrit. 2 (84.8%)

Eye Dam. 1 (89.1%)

STOT SE 3 (84.8%)

Skin Irrit. 2 (97.5%)

Eye Irrit. 2 (97.5%)

STOT SE 3 (100%)

8.1.3 Hazards Summary

Intravenous LD50 (mouse) = 56 mg/kg; [RTECS] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS]

8.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
2-Butenoic acid, 4-bromo-, methyl 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 Adverse Effects

Dermatotoxin - Skin burns.

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

9.1.2 Acute Effects

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

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 UN GHS Classification

13.3 NORMAN Suspect List Exchange Classification

13.4 EPA DSSTox Classification

13.5 EPA TSCA and CDR Classification

13.6 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
    2-Butenoic acid, 4-bromo-, methyl ester
    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. 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/
  8. 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
  9. 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
    Methyl 4-bromocrotonate
    https://haz-map.com/Agents/20825
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. 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
    2-Butenoic acid, 4-bromo-, methyl ester
    http://www.nist.gov/srd/nist1a.cfm
  12. SpectraBase
    2-BUTENOIC ACID, 4-BROMO-, METHYL ESTER
    https://spectrabase.com/spectrum/HWtbmhvg28S
    Methyl (2E)-4-bromo-2-butenoate
    https://spectrabase.com/spectrum/r6GooeQ2Bc
    (E)-METHYL-4-BROMOBUT-2-ENOATE
    https://spectrabase.com/spectrum/3VRqw6Z7DI5
  13. NMRShiftDB
  14. Springer Nature
  15. SpringerMaterials
  16. 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/
  17. Wikidata
    methyl (E)-4-bromobut-2-enoate
    https://www.wikidata.org/wiki/Q76305518
  18. Wiley
  19. PubChem
  20. GHS Classification (UNECE)
  21. 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/
  22. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  23. PATENTSCOPE (WIPO)
CONTENTS