Isopropyl iodide: Difference between revisions

Browse history interactively ← Previous editContent deleted Content addedVisual WikitextInline

Revision as of 19:31, 29 June 2011 editVCalvoP (talk \| contribs)59 editsNo edit summary← Previous edit		Latest revision as of 18:20, 9 September 2022 edit undo88.115.34.218 (talk) →Preparation
(31 intermediate revisions by 21 users not shown)
Line 1:		Line 1:
	{{~~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-propyl
			\| ImageName1 = Spacefill model of isopropyl iodide
	iodide, sec-propyl iodide
			\| 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>
	\| Section1 = {{Chembox Identifiers
			\|Section1={{Chembox Identifiers
	\| SMILES = CC(I)C
	\| CASNo = 75-30-9		\| CASNo = 75-30-9
	\| CASNo_Ref = {{cascite}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| RTECS = TZ4200000
			\| UNII = 67K05OPZ0E
	}}
			\| PubChem = 6362
	\| Section2 = {{Chembox Properties
			\| ChemSpiderID = 6122
	\| Formula = C<sub>3</sub>H<sub>7</sub>I
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\| MolarMass = 169.99
			\| EINECS = 200-859-3
	\| Appearance = Colourless liquid
	\| ~~Density~~ = ~~1.703~~		\| UNNumber = 2392
			\| MeSHName = isopropyl+iodide
	\| Solubility = 0.14 g/100 ml at 12.5 °C
			\| RTECS = TZ4200000
	\| Solubility1 = fully ]
	\| ~~Solvent1~~ = ~~ethanol~~		\| Beilstein = 1098244
			\| SMILES = CC(C)I
	\| Solubility2 = fully ]
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
	\| Solvent2 = diethyl ether
			\| StdInChI = 1S/C3H7I/c1-3(2)4/h3H,1-2H3
	\| Solubility3 = fully ]
			\| StdInChIKey = FMKOJHQHASLBPH-UHFFFAOYSA-N
	\| Solvent3 = chloroform
			\| StdInChIKey_Ref = {{chemspidercite\|correct\|chemspider}}
	\| Solubility4 = fully ]
	\| 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
			\| 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==
	'''Isopropyl iodide''' (also ''iododimethylmethane, 2-propyl iodide, sec-propyl iodide or 2-iodopropane'') is a ], ] ]. It has the chemical formula C<sub>3</sub>H<sub>7</sub>I and is prepared by distilling isopropyl alcohol with ], or with ], ], and ].<ref name="merck">Merck Index of Chemicals and Drugs, 9th ed., monograph 5074</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 + NaI → (CH<sub>3</sub>)<sub>2</sub>CHI + NaBr

	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}}
			{{Organohalide-stub}}

	]


	{{organohalide-stub}}

	]		]
			]
	]
			]
	]

Latest revision as of 18:20, 9 September 2022

Isopropyl iodide
Names


Preferred IUPAC name 2-Iodopropane
Identifiers
CAS Number	75-30-9
3D model (JSmol)	Interactive image
Beilstein Reference	1098244
ChemSpider	6122
ECHA InfoCard	100.000.782
EC Number	200-859-3
MeSH	isopropyl+iodide
PubChem CID	6362
RTECS number	TZ4200000
UNII	67K05OPZ0E
UN number	2392
CompTox Dashboard (EPA)	DTXSID4058788
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 (k_H)	890 nmol Pa kg
Refractive index (n_D)	1.4997
Viscosity	6.971 mPa (at 20 °C)
Thermochemistry
Heat capacity (C)	137.3 J K mol
Std enthalpy of formation (Δ_fH₂₉₈)	−77.2–−72.6 kJ mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H302
Flash point	42 °C (108 °F; 315 K)
Related compounds
Related alkanes	Ethane Ethyl iodide Propane n-Propyl iodide Butane Butyl iodide
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

"isopropyl iodide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 3 March 2012.
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.

Categories: