Isopropyl iodide

Last updated
Isopropyl iodide
Skeletal formula of isopropyl iodide Isopropyl iodide stick.png
Skeletal formula of isopropyl iodide
Spacefill model of isopropyl iodide IsopropylIodide.png
Spacefill model of isopropyl iodide
Names
Preferred IUPAC name
2-Iodopropane [1]
Identifiers
3D model (JSmol)
1098244
ChemSpider
ECHA InfoCard 100.000.782 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-859-3
MeSH isopropyl+iodide
PubChem CID
RTECS number
  • TZ4200000
UNII
UN number 2392
  • InChI=1S/C3H7I/c1-3(2)4/h3H,1-2H3 X mark.svgN
    Key: FMKOJHQHASLBPH-UHFFFAOYSA-N Yes check.svgY
  • CC(C)I
Properties
C3H7I
Molar mass 169.993 g·mol−1
AppearanceColourless liquid
Density 1.703 g mL−1
Melting point −90.00 °C; −130.00 °F; 183.15 K
Boiling point 88.8 to 89.8 °C; 191.7 to 193.5 °F; 361.9 to 362.9 K
1.4 g L−1 (at 12.5 °C)
Solubility in chloroform Miscible
Solubility in ethanol Miscible
Solubility in diethyl ether Miscible
Solubility in benzene Miscible
890 nmol Pa−1 kg−1
1.4997
Viscosity 6.971 mPa (at 20 °C)
Thermochemistry
137.3 J K−1 mol−1
−77.2–−72.6 kJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H226, H302
Flash point 42 °C (108 °F; 315 K)
Related compounds
Related alkanes
Related compounds
Diiodohydroxypropane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Isopropyl iodide is the organoiodine compound with the formula (CH3)2CHI. It is colorless, flammable, and volatile. Organic iodides are light-sensitive and take on a yellow colour upon storage, owing to the formation of iodine.

Preparation

Isopropyl iodide is prepared by iodination of isopropyl alcohol using hydrogen iodide or, equivalently, with a mixture of glycerol, iodine, and phosphorus. [2] An alternative preparation involves the reaction of 2-propyl bromide with an acetone solution of sodium iodide (Finkelstein reaction): [3]

(CH3)2CHBr + NaI → (CH3)2CHI + NaBr

References

  1. "isopropyl iodide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 3 March 2012.
  2. Merck Index of Chemicals and Drugs, 9th ed., monograph 5074
  3. Textbook of Practical Organic Chemistry, 5th Edition, Prentice Hall, 1989