| 词条 | Iodobenzene dichloride |
| 释义 |
| Watchedfields = changed | verifiedrevid = 432357218 | Reference = [1] | ImageFileL1 = PhICl2-2D-skeletal-with-explicit-lone-pair-stereochemistry.png | ImageAltL1 = | ImageFileR1 = PhICl2-from-xtal-1996-3D-CM-balls.png | ImageAltR1 = | IUPACName = (Dichloro-λ3-iodanyl)benzene | OtherNames = Iodosobenzene dichloride; Phenyliodine(III) dichloride; Phenyliodo dichloride; Phenyliodoso chloride; Phenylchloroiodonium chloride; Dichloroiodobenzene; Iododichlorobenzene |Section1={{Chembox Identifiers | Abbreviations = IBD | CASNo_Ref = {{cascite|correct|??}} | CASNo = 932-72-9 | PubChem = 13166207 | ChemSpiderID = 254526 | SMILES = Cl[I](c1ccccc1)Cl}} |Section2={{Chembox Properties | C=6 | H=5 | I=1 | Cl=2 | MolarMass = | Appearance = Yellow solid | Density = 2.2 g/cm3 | MeltingPtC = 115 to 120 | MeltingPt_notes = (decomposes) | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} Iodobenzene dichloride (PhICl2) is a complex of iodobenzene with chlorine. As a reagent for organic chemistry, it is used as an oxidant and chlorinating agent. Chemical structureSingle-crystal X-ray crystallography has been used to determine its structure; as can be predicted by VSEPR theory, it adopts a T-shaped geometry about the central iodine atom.[2][3]PreparationIodobenzene dichloride is not stable, and is not commonly available commercially. It is prepared by passing chlorine gas through a solution of iodobenzene in chloroform, from which it precipitates.[4] The same reaction has been reported at pilot plant scale (20 kg) as well.[5] Ph-I + Cl2 → PhICl2 An alternate preparation involving the use of chlorine generated in situ by the action of sodium hypochlorite on hydrochloric acid has also been described.[6] ReactionsIodobenzene dichloride is hydrolyzed by basic solutions to give iodosobenzene (PhIO),[7] and is oxidized by sodium hypochlorite to give iodoxybenzene (PhIO2).[8] In organic synthesis, iodobenzene dichloride is used as a reagent for the selective chlorination of alkenes[1] and alkynes.[9] References1. ^1 Phenyliodine(III) Dichloride, David W. Knight and Glen A. Russell, in Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons, Ltd {{DOI|10.1002/047084289X.rp071}} 2. ^{{cite journal | journal = Acta Crystallogr.| year = 1953 | volume = 6 | pages = 88–92 | doi = 10.1107/S0365110X53000193 | title = The crystal structure of benzene iododichloride | author = E. M. Archer and T. G. van Schalkwy}} 3. ^{{ cite journal |author1=J. V. Carey |author2=P. A. Chaloner |author3=P. B. Hitchcock |author4=T. Neugebauer |author5=K. R. Seddon|title= Synthesis and decomposition of dichloroiodoarenes - An improved low temperature X-ray structure of dichloroiodobenzene and the structure OFORO-2,3,5,6-TETRAKIS(CHLOROMETHYL)-4-METHYLBENZENE | journal = J. Chem. Res. |issue=8|year = 1996 | volume = 358 | pages = 2031– }} 4. ^{{OrgSynth | title = Iodobenzene dichloride | author = H. J. Lucas and E. R. Kennedy | prep = cv3p0482 | collvol = 3 | collvolpages = 482}} 5. ^{{cite journal | doi = 10.1021/op980024e | title = Large-Scale Preparation of Iodobenzene Dichloride and Efficient Monochlorination of 4-Aminoacetophenone | year = 1998 | last1 = Zanka | first1 = Atsuhiko | last2 = Takeuchi | first2 = Hiroki | last3 = Kubota | first3 = Ariyoshi | journal = Organic Process Research & Development | volume = 2 | pages = 270 | issue = 4}} 6. ^{{cite journal | doi = 10.1055/s-2007-965889 | journal = Synthesis | title = Iodobenzene Dichloride as a Stoichiometric Oxidant for the Conversion of Alcohols into Carbonyl Compounds; Two Facile Methods for Its Preparation | year = 2007 | last1 = Zhao | first1 = Xue-Fei | last2 = Zhang | first2 = Chi | volume = 2007 | pages = 551 | issue = 4}} 7. ^{{OrgSynth | collvol = 3 | collvolpages = 483 | year = 1955 | title = Iodosobenzene | author = H. J. Lucas, E. R. Kennedy, and M. W. Formo | prep = cv3p0483}} 8. ^{{OrgSynth | collvol = 3 | collvolpages = 485 | year = 1955 | title = Iodoxybenzene: B. Hypochlorite oxidation of iodobenzene dichloride | author = M. W. Formo and John R. Johnson | prep = cv3p0485}} 9. ^{{cite journal | author = Michael E. Jung and Michael H. Parker | title = Synthesis of Several Naturally Occurring Polyhalogenated Monoterpenes of the Halomon Class | journal = Journal of Organic Chemistry | year = 1997 | volume = 62 | issue = 21 | pages = 7094–7095 | doi = 10.1021/jo971371 | pmid=11671809}} Further reading
4 : Iodanes|Oxidizing agents|Reagents for organic chemistry|Phenyl compounds |
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