Chloroiodomethane

Last updated
Chloroiodomethane
Stereo, skeletal formula of chloroiodomethane with all explicit hydrogens added Chloroiodomethane.svg
Stereo, skeletal formula of chloroiodomethane with all explicit hydrogens added
Spacefill model of chloroiodomethane Chloroiodomethane-3D-vdW.png
Spacefill model of chloroiodomethane
Names
Preferred IUPAC name
Chloro(iodo)methane
Other names
  • Chloroiodomethane
  • Chloroiodomethane
  • Chloromethyl iodide
Identifiers
3D model (JSmol)
1730802
ChemSpider
ECHA InfoCard 100.008.915 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-804-8
PubChem CID
UNII
  • InChI=1S/CH2ClI/c2-1-3/h1H2 Yes check.svgY
    Key: PJGJQVRXEUVAFT-UHFFFAOYSA-N Yes check.svgY
  • ClCI
Properties
CH2ClI
Molar mass 176.38 g·mol−1
AppearanceColorless liquid
Density 2.422 g mL−1
Boiling point 108 to 109 °C (226 to 228 °F; 381 to 382 K)
8.9 μmol Pa−1 kg−1
1.582
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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
Related compounds
 2-Chloroethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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

Contents

Applications

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

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

References

  1. 1 2 Miyano, Sotaro; Friestad, Gregory K. (2008). "Chloroiodomethane". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc110.pub2. ISBN   978-0471936237.
  2. ↑ 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.
  3. ↑ Donald S. Matteson (2001). "Chloromethyllithium". EEROS. doi:10.1002/047084289X.rc117. ISBN   0471936235.
  4. ↑ 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.
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