Jump to content
 







Main menu
    


Navigation  


●Main page
 ●Contents
 ●Current events
 ●Random article
 ●About Wikipedia
 ●Contact us
 ●Donate
  



Contribute  


●Help
 ●Learn to edit
 ●Community portal
 ●Recent changes
 ●Upload file
  







Search  

































●Create account

●Log in
 









●Create account
 ● Log in
  



Pages for logged out editors learn more  


●Contributions
 ●Talk
  


















Contents

   



(Top)
  


1 Applications  




2 Crystallography  




3 References  




4 External links  













Chloroiodomethane






●تۆرکجه
 ●Deutsch
 ●Ελληνικά
 ●فارسی
 ●Français
 ●Italiano
 ●Magyar
 ●Nederlands
 ●日本語
 ●Српски / srpski
 ●Srpskohrvatski / српскохрватски
 ●Suomi
 ●Tagalog
 ●தமிழ்
 ●中文
  
Edit links
  








●Article
 ●Talk
  
















●Read
 ●Edit
 ●View history
  







Tools
    


Actions  


●Read
 ●Edit
 ●View history
  



General  


●What links here
 ●Related changes
 ●Upload file
 ●Special pages
 ●Permanent link
 ●Page information
 ●Cite this page
 ●Get shortened URL
 ●Download QR code
 ●Wikidata item
  



Print/export  


●Download as PDF
 ●Printable version
  



In other projects  


●Wikimedia Commons
  















Appearance
    

 





From Wikipedia, the free encyclopedia
  

Chloroiodomethane
Stereo, skeletal formula of chloroiodomethane with all explicit hydrogens added
Spacefill model of chloroiodomethane
Names
Preferred IUPAC name

Chloro(iodo)methane

Other names
  • Chloroiodomethane
  • Chloroiodomethane
  • Chloromethyl iodide
    • Identifiers

    CAS Number

    3D model (JSmol)

    Beilstein Reference

    		 1730802
    ChemSpider
    ECHA InfoCard 100.008.915 Edit this at Wikidata
    EC Number
    • 209-804-8

    PubChem CID
    UNII

    CompTox Dashboard (EPA)

    • InChI=1S/CH2ClI/c2-1-3/h1H2 checkY

      Key: PJGJQVRXEUVAFT-UHFFFAOYSA-N checkY

    • ClCI

    Properties

    Chemical formula

    		 CH2ClI
    Molar mass 176.38 g·mol−1
    Appearance Colorless liquid
    Density 2.422 g mL−1
    Boiling point 108 to 109 °C (226 to 228 °F; 381 to 382 K)

    Henry's law
    constant     (kH)

    		 8.9 μmol Pa−1kg−1

    Refractive index (nD)

    		 1.582
    Hazards
    GHS labelling:

    Pictograms

    		 GHS07: Exclamation mark

    Signal word

    		 Warning

    Hazard statements

    		 H315, H319, H335

    Precautionary statements

    		 P261, P305+P351+P338
    NFPA 704 (fire diamond)
    NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
    1
    1
    0
    Related compounds

    Related alkanes
  • Bromochloromethane
  • Dibromochloromethane

    • Related compounds

    		 2-Chloroethanol

    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

    checkY verify (what is checkY☒N ?)

    Infobox references

    Chloroiodomethane is the halomethane with the formula is CH
    2    ClI    . It is a colorless liquid of use in organic synthesis.[1] Together with other iodomethanes, chloroiodomethane is produced by some microorganisms.[2]

    Applications[edit]

    Chloroiodomethane is used in cyclopropanation (Simmon-Smith reaction), where it often replaces diiodomethane because of higher yields and selectivity. It is also used in Mannich reaction, aminomethylation, epoxidation, ring opening and addition to terminal alkenes. It is a precursor to agent Ph3P=CHCl that can add a chloromethylene group (=CHCl).[1] It reacts with organolithium compounds to give chloromethyl lithium (ClCH2Li).[3]

    Crystallography[edit]

    It crystallizes orthorhombic crystal system with space group Pnma with lattice constants: a = 6.383, b = 6.706, c = 8.867 (.10−1nm).[4]

    References[edit]

    1. ^ a b Miyano, Sotaro; Friestad, Gregory K. (2008). "Chloroiodomethane". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc110.pub2. ISBN 978-0471936237.
  • ^ Fuse, Hiroyuki; Inoue, Hiroyuki; Murakami, Katsuji; Takimura, Osamu; Yamaoka, Yukiho (2003). "Production of free and organic iodine by Roseovarius spp.". FEMS Microbiology Letters. 229 (2): 189–94. doi:10.1016/S0378-1097(03)00839-5. PMID 14680698.
  • ^ Donald S. Matteson (2001). "Chloromethyllithium". EEROS. doi:10.1002/047084289X.rc117. ISBN 0471936235.
  • ^ Torrie B. H.; Binbrek O. S.; von Dreele R. (1993). "Crystal structure of chloroiodomethane". Mol. Phys. 79 (4): 869–874(6). Bibcode:1993MolPh..79..869T. doi:10.1080/00268979300101691.

    • External links[edit]


    Stub icon

    This article about an organic halide is a stub. You can help Wikipedia by expanding it.

  • t
  • e

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Chloroiodomethane&oldid=1146991250"
    Categories: 
    ●Halomethanes
     ●Organochlorides
     ●Organoiodides
     ●Organohalide stubs
     Hidden categories: 
    ●Articles without InChI source
     ●Articles without EBI source
     ●Articles without KEGG source
     ●ECHA InfoCard ID from Wikidata
     ●Chembox having GHS data
     ●Articles containing unverified chemical infoboxes
     ●Chembox image size set
     ●Articles with short description
     ●Short description matches Wikidata
     ●All stub articles
      


    ●This page was last edited on 28 March 2023, at 05:41 (UTC).
    ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.


    ●Privacy policy
    ●About Wikipedia
    ●Disclaimers
    ●Contact Wikipedia
    ●Code of Conduct
    ●Developers
    ●Statistics
    ●Cookie statement
    ●Mobile view


    Wikimedia Foundation
    Powered by MediaWiki