Iodocyclopropane

Iodocyclopropane is a organoiodine compound with the chemical formula C3H5I.[1][2] The compound is a member of haloalkane family.

Iodocyclopropane
Names
Preferred IUPAC name
Iodocyclopropane
Other names
Cyclopropyl iodide, cyclopropyliodide
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 818-892-2
  • InChI=1S/C3H5I/c4-3-1-2-3/h3H,1-2H2
    Key: VLODBNNWEWTQJX-UHFFFAOYSA-N
  • C1CC1I
Properties
C3H5I
Molar mass 167.977 g·mol−1
Appearance Liquid
Density g/cm3
Hazards
GHS labelling:
GHS07: Exclamation mark
H315, H319, H335
Related compounds
Related compounds
 Fluorocyclopropane
Bromocyclopropane
Bromocyclopropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

Iodocyclopropane can be prepared by photochemical iodination of cyclopropane.

(CH2)3 + I2 → HI + C3H5I

Chemical properties

The compound reacts with benzoxazole to produce 2-cyclopropylbenzoxazole in presence of palladium catalyst.[3]

Uses

Iodocyclopropanes are used as synthetic intermediates to synthesize many alkyl, aryl, and acyl substituted cyclopropanes via organometallic reactions.[4]

See also

References
  1. "Iodocyclopropane". Manchester Organics. Retrieved 31 May 2023.
  2. "Iodocyclopropane". Sigma Aldrich. Retrieved 31 May 2023.
  3. Wu, Xiaojin; Lei, Chuanhu; Yue, Guizhou; Zhou, Jianrong Steve (10 August 2015). "Palladium-Catalyzed Direct Cyclopropylation of Heterocycles". Angewandte Chemie International Edition. 54 (33): 9601–9605. doi:10.1002/anie.201504735. hdl:10356/89367. PMID 26179255.
  4. Martin, Stephen F.; Dwyer, Michael P. (19 March 1998). "Iodocyclopropanes as versatile intermediates for the synthesis of substituted cyclopropanes". Tetrahedron Letters. 39 (12): 1521–1524. doi:10.1016/S0040-4039(98)00072-0. ISSN 0040-4039. Retrieved 31 May 2023.
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