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Chloroiodomethane

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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
  • InChI=1S/CH2ClI/c2-1-3/h1H2Key: PJGJQVRXEUVAFT-UHFFFAOYSA-N
SMILES
  • ClCI
Properties
Chemical formula CH2ClI
Molar mass 176.38 g·mol
Appearance Colorless liquid
Density 2.422 g mL
Boiling point 108 to 109 °C (226 to 228 °F; 381 to 382 K)
Henry's law
constant (kH) 		8.9 μmol Pa kg
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
Related compounds 2-Chloroethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

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). It reacts with organolithium compounds to give chloromethyl lithium (ClCH2Li).

Crystallography

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

References

  1. ^ 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.

External links

Halomethanes
Unsubstituted
Monosubstituted
Disubstituted
Trisubstituted
Tetrasubstituted
* Chiral compound.


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