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Methyllithium

PubChem CID
2724049
Structure
Methyllithium_small.png
Methyllithium_3D_Structure.png
Molecular Formula
Synonyms
  • Methyllithium
  • 917-54-4
  • Lithium, methyl-
  • Methyl lithium
  • lithium;carbanide
Molecular Weight
22.0 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Parent Compound
Dates
  • Create:
    2005-07-19
  • Modify:
    2025-01-25
Description
Methyllithium is an alkyllithium compound and a one-carbon compound.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Methyllithium.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

lithium;carbanide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/CH3.Li/h1H3;/q-1;+1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

[Li+].[CH3-]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

CH3Li
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

917-54-4

2.3.2 Deprecated CAS

12540-68-0, 33825-29-5
33825-29-5

2.3.3 European Community (EC) Number

2.3.4 ChEBI ID

2.3.5 DSSTox Substance ID

2.3.6 Wikidata

2.3.7 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

methyllithium

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
22.0 g/mol
Reference
Computed by PubChem 2.2 (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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
22.03947853 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
22.03947853 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
0 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
2
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
2
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
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

Metals -> Metals, Organic Compounds

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

6 Chemical Vendors

7 Use and Manufacturing

7.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
Lithium, methyl-: ACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Flammable
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

H224 (11.4%): Extremely flammable liquid and vapor [Danger Flammable liquids]

H250 (100%): Catches fire spontaneously if exposed to air [Danger Pyrophoric liquids]

H252 (11.4%): Self-heating in large quantities; may catch fire [Warning Self-heating substances and mixtures]

H260 (100%): In contact with water releases flammable gases which may ignite spontaneously [Danger Substances and mixtures which in contact with water, emit flammable gases]

H302 (11.4%): Harmful if swallowed [Warning Acute toxicity, oral]

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H336 (11.4%): May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects]

H412 (71.4%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P210, P222, P223, P231, P231+P232, P233, P235, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P317, P301+P330+P331, P302+P335+P334, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P319, P321, P330, P363, P370+P378, P402+P404, P403+P233, P403+P235, P405, P407, P410, P413, P420, 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 35 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

Pyr. Liq. 1 (100%)

Water-react. 1 (100%)

Skin Corr. 1 (100%)

Aquatic Chronic 3 (71.4%)

8.1.3 Hazards Summary

Methyllithium is pyrophoric, violently reactive with water (evolves flammable gases), and corrosive; Available in solution of 60-100% cumene (CAS# 98-82-8) and 10-30% tetrahydro-2-methylfuran (CAS# 96-47-9); [Sigma-Aldrich MSDS] See Lithium.

8.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Lithium, methyl-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Lithium, methyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

8.3 Other Safety Information

Chemical Assessment

IMAP assessments - Lithium, methyl-: Environment tier I assessment

IMAP assessments - Lithium, methyl-: Human health tier I assessment

9 Toxicity

9.1 Toxicological Information

9.1.1 Adverse Effects

Dermatotoxin - Skin burns.

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Thieme References

10.5 Wiley References

10.6 Nature Journal References

10.7 Chemical Co-Occurrences in Literature

10.8 Chemical-Gene Co-Occurrences in Literature

10.9 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 Classification

12.1 MeSH Tree

12.2 ChEBI Ontology

12.3 ChemIDplus

12.4 UN GHS Classification

12.5 NORMAN Suspect List Exchange Classification

12.6 EPA DSSTox Classification

12.7 EPA TSCA and CDR Classification

12.8 EPA Substance Registry Services Tree

12.9 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. 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
  6. 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/
  7. ChEBI
  8. 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
  9. Nature Chemistry
  10. NMRShiftDB
  11. Springer Nature
  12. 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/
  13. Wikidata
  14. Wikipedia
  15. Wiley
  16. PubChem
  17. 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
  18. GHS Classification (UNECE)
  19. 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/
  20. EPA Substance Registry Services
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  22. PATENTSCOPE (WIPO)
CONTENTS