| Revision as of 19:31, 29 June 2011 editVCalvoP (talk | contribs)59 editsNo edit summary← Previous edit | Revision as of 00:57, 12 August 2011 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,701 edits trim procedural details (WP:NOTMANUAL)Next edit → | ||
| Line 9: | Line 9: | ||
| | ImageName = | | ImageName = | ||
| | IUPACName = 2-iodopropane | | IUPACName = 2-iodopropane | ||
| | OtherNames = iododimethylmethane, isopropyl iodide, 2-propyl | | OtherNames = iododimethylmethane, isopropyl iodide, 2-propyliodide, sec-propyl iodide | ||
| iodide, sec-propyl iodide | |||
| | Section1 = {{Chembox Identifiers | | Section1 = {{Chembox Identifiers | ||
| | SMILES = CC(I)C | | SMILES = CC(I)C | ||
| Line 54: | Line 53: | ||
| }} | }} | ||
| '''Isopropyl iodide''' |
'''Isopropyl iodide''' is the ] with the ] (CH<sub>3</sub>)<sub>2</sub>CHI. It is ], ], and volatile. Organic iodides are light-sensitive and take on a yellow colour upon storage, owing to the formation of ]. | ||
| ==Preparation== | |||
| Isopropyl iodide is prepared by iodination of ] using ] or, equivalently, with a mixture of ], ], and ].<ref name="merck">Merck Index of Chemicals and Drugs, 9th ed., monograph 5074</ref> An alternative preparation involves the reaction of 2-propyl bromide with an acetone solution of potassium iodide (KI):<ref>Textbook of Practical Organic Chemistry, 5th Edition, Prentice Hall, 1989</ref> | |||
| :(CH<sub>3</sub>)<sub>2</sub>CHBr + KI → (CH<sub>3</sub>)<sub>2</sub>CHI + KBr | |||
| The most cited path to alkyl iodides include the typical halogenation using a 57% HI solution and 2-propanol, but the regioselectivity is improved using PI3 prepared in-situ. | |||
| An alternative preparation involves halide exchange using potassium iodide (KI: 0.25 mol) dissolved in dry dimethylcetone. A solution of 0.2 mol of 2-propyl bromide in dry acetone (250 mL) is allowed to react at room temperature with dry KI freshly disolved in acetone. A fine precipitate of potassium bromide forms immediately. The reaction is allowed to proceed under reflux and fractional distillation is required to boil of the dimethylcetone and unreacted 2-propyl-bromide. The 2-propyl iodide boils of between 87 to 89 °C. Good to moderate yield (70%) is obtained within 60 minutes. | |||
| The reaction is believed to occur via S<sub>N</sub>2 mechanism, therefore an inversion of configuration is expected for chiral halides. This reaction path is preferable for the synthesis of 1-propyl iodide. These organic halides shall not be stored because are light sensitive and iodine slowly develops even in the dark. | |||
| <ref>Textbook of Practical Organic Chemistry, 5th Edition, Prentice Hall, 1989</ref> | |||
| ==References== | ==References== | ||
| {{reflist|1}} | {{reflist|1}} | ||
Revision as of 00:57, 12 August 2011
| |
| |
| Names | |
|---|---|
| IUPAC name 2-iodopropane | |
| Other names iododimethylmethane, isopropyl iodide, 2-propyliodide, sec-propyl iodide | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ECHA InfoCard | 100.000.782 
|
| RTECS number |
|
| CompTox Dashboard (EPA) | |
SMILES
| |
| Properties | |
| Chemical formula | C3H7I |
| Molar mass | 169.99 |
| Appearance | Colourless liquid |
| Density | 1.703 |
| Melting point | −90.0 °C (−130.0 °F; 183.2 K) |
| Boiling point | 89.5 °C (193.1 °F; 362.6 K) |
| Solubility in water | 0.14 g/100 ml at 12.5 °C |
| Solubility in ethanol | fully miscible |
| Solubility in diethyl ether | fully miscible |
| Solubility in chloroform | fully miscible |
| Solubility in benzene | fully miscible |
| Refractive index (nD) | 1.4997 |
| Viscosity | 8.841 cP at 0 °C 6.971 cP at 20 °C |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
| Main hazards | Possible carcinogen. Harmful if swallowed, inhaled and in contact with skin. Eye, respiratory and mucous membrane irritant. |
| Flash point | 42 °C |
| Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
| |
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 potassium iodide (KI):
- (CH3)2CHBr + KI → (CH3)2CHI + KBr
References
- Merck Index of Chemicals and Drugs, 9th ed., monograph 5074
- Textbook of Practical Organic Chemistry, 5th Edition, Prentice Hall, 1989
 | This article about an organic halide is a stub. You can help Misplaced Pages by expanding it. |