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Isopropyl iodide: Difference between revisions

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Revision as of 00:57, 12 August 2011 editSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,227 edits trim procedural details (WP:NOTMANUAL)← Previous edit Latest revision as of 18:20, 9 September 2022 edit undo88.115.34.218 (talk) Preparation 
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{{chembox {{Chembox
| Verifiedfields = changed
| verifiedrevid = 293599230
| Watchedfields = changed
| Name = Isopropyl iodide
| verifiedrevid = 444362078
| ImageFile1 = isopropyl iodide stick.png
| ImageFile = isopropyl iodide stick.png
| ImageSize1 = 150px
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageName1 =
| ImageSize = 100
| ImageFile = IsopropylIodide.png
| ImageName = Skeletal formula of isopropyl iodide
| ImageSize =200px
| ImageFile1 = IsopropylIodide.png
| ImageName =
| ImageFile1_Ref = {{chemboximage|correct|??}}
| IUPACName = 2-iodopropane
| ImageSize1 = 160
| OtherNames = iododimethylmethane, isopropyl iodide, 2-propyliodide, sec-propyl iodide
| ImageName1 = Spacefill model of isopropyl iodide
| Section1 = {{Chembox Identifiers
| PIN = 2-Iodopropane<ref>{{Cite web|title=isopropyl iodide - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6362&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=3 March 2012|location=USA|date=27 March 2005|at=Identification and Related Records}}</ref>
| SMILES = CC(I)C
|Section1={{Chembox Identifiers
| CASNo = 75-30-9
| CASNo = 75-30-9
| CASNo_Ref = {{cascite}}
| CASNo_Ref = {{cascite|correct|CAS}}
| RTECS = TZ4200000
| UNII_Ref = {{fdacite|correct|FDA}}
}}
| UNII = 67K05OPZ0E
| Section2 = {{Chembox Properties
| PubChem = 6362
| Formula = C<sub>3</sub>H<sub>7</sub>I
| MolarMass = 169.99 | ChemSpiderID = 6122
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| Appearance = Colourless liquid
| Density = 1.703 | EINECS = 200-859-3
| UNNumber = 2392
| Solubility = 0.14 g/100 ml at 12.5 °C
| MeSHName = isopropyl+iodide
| Solubility1 = fully ]
| Solvent1 = ethanol | RTECS = TZ4200000
| Beilstein = 1098244
| Solubility2 = fully ]
| SMILES = CC(C)I
| Solvent2 = diethyl ether
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| Solubility3 = fully ]
| StdInChI = 1S/C3H7I/c1-3(2)4/h3H,1-2H3
| Solvent3 = chloroform
| StdInChIKey = FMKOJHQHASLBPH-UHFFFAOYSA-N
| Solubility4 = fully ]
| StdInChIKey_Ref = {{chemspidercite|correct|chemspider}}
| Solvent4 = benzene
| RefractIndex = 1.4997
| MeltingPtC = -90.0
| BoilingPtC = 89.5
| pKa =
| Viscosity = 8.841 c] at 0 °C<br/>6.971 c] at 20 °C
| Dipole =
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| FlashPt = 42 °C
| MainHazards = Possible carcinogen. Harmful if swallowed, inhaled and in contact with skin. Eye, respiratory and mucous membrane irritant.
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-O =
| RPhrases = R20 R21 R22 R36 R37 R38 R40
| SPhrases = S16 S23 S26 S36
}}
| Section8 = {{Chembox Related
| Function = ]s
| OtherFunctn = ]<br>]<br>] }}
}} }}
|Section2={{Chembox Properties

| C=3 | H=7 | I=1
'''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 ].
| Appearance = Colourless liquid
| Density = 1.703 g mL<sup>−1</sup>
| BoilingPtK = 361.9 to 362.9
| MeltingPtK = 183.15
| Solubility = 1.4 g L<sup>−1</sup> (at 12.5 °C)
| Solvent1 = chloroform
| Solubility1 = Miscible
| Solvent2 = ethanol
| Solubility2 = Miscible
| Solvent3 = diethyl ether
| Solubility3 = Miscible
| Solvent4 = benzene
| Solubility4 = Miscible
| HenryConstant = 890 nmol Pa<sup>−1</sup> kg<sup>−1</sup>
| RefractIndex = 1.4997
| Viscosity = 6.971 mPa (at 20 °C)
}}
|Section3={{Chembox Thermochemistry
| DeltaHf = −77.2–−72.6 kJ mol<sup>−1</sup>
| HeatCapacity = 137.3 J K<sup>−1</sup> mol<sup>−1</sup>
}}
|Section4={{Chembox Hazards
| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
| GHSSignalWord = '''WARNING'''
| HPhrases = {{H-phrases|226|302}}
| FlashPtC = 42
}}
|Section5={{Chembox Related
| OtherFunction_label = alkanes
| OtherFunction = {{Unbulleted list|]|]|]|]|]|]}}
| OtherCompounds = ]
}}
}}
'''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== ==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> 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 ] with an acetone solution of ] (]):<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 :(CH<sub>3</sub>)<sub>2</sub>CHBr + NaI → (CH<sub>3</sub>)<sub>2</sub>CHI + NaBr


==References== ==References==
{{reflist|1}} {{Reflist}}
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