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Isopropyl iodide

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Isopropyl iodide
Skeletal formula of isopropyl iodide
Spacefill model of isopropyl iodide
Names
Preferred IUPAC name 2-Iodopropane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1098244
ChemSpider
ECHA InfoCard 100.000.782 Edit this at Wikidata
EC Number
  • 200-859-3
MeSH isopropyl+iodide
PubChem CID
RTECS number
  • TZ4200000
UNII
UN number 2392
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H7I/c1-3(2)4/h3H,1-2H3Key: FMKOJHQHASLBPH-UHFFFAOYSA-N
SMILES
  • CC(C)I
Properties
Chemical formula C3H7I
Molar mass 169.993 g·mol
Appearance Colourless liquid
Density 1.703 g mL
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
Solubility in water 1.4 g L (at 12.5 °C)
Solubility in chloroform Miscible
Solubility in ethanol Miscible
Solubility in diethyl ether Miscible
Solubility in benzene Miscible
Henry's law
constant (kH) 		890 nmol Pa kg
Refractive index (nD) 1.4997
Viscosity 6.971 mPa (at 20 °C)
Thermochemistry
Heat capacity (C) 137.3 J K mol
Std enthalpy of
formation (ΔfH298) 		−77.2–−72.6 kJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS07: Exclamation mark
Signal word Warning
Hazard statements 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. An alternative preparation involves the reaction of 2-propyl bromide with an acetone solution of sodium iodide (Finkelstein reaction):

(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
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