Chloroiodomethane

Last updated
Chloroiodomethane
Chloroiodomethane.svg
Chloroiodomethane-3D-vdW.png
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)
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).
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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]

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 chloromethylenating agent Ph3P=CHCl. [1] It reacts with organolithium compounds to give chloromethyllithium (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]

Related Research Articles

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3
CO
2
). The hydrated derivative, Cu2(OAc)4(H2O)2, which contains one molecule of water for each copper atom, is available commercially. Anhydrous copper(II) acetate is a dark green crystalline solid, whereas Cu2(OAc)4(H2O)2 is more bluish-green. Since ancient times, copper acetates of some form have been used as fungicides and green pigments. Today, copper acetates are used as reagents for the synthesis of various inorganic and organic compounds. Copper acetate, like all copper compounds, emits a blue-green glow in a flame.

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Acyl cyanide

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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.