Iodine monochloride 5575149 215999617 2008-05-30T17:00:34Z Thijs!bot 1392310 robot Adding: [[zh:一氯化碘]] {{Chembox new | Name = Iodine monochloride | ImageFile = Iodine-monochloride-2D.png <!-- | ImageSize = 100px --> | ImageName = Iodine monochloride | ImageFile1 = Iodine-monochloride-3D-vdW.png <!-- | ImageSize1 = 100px --> | ImageName1 = Iodine monochloride | IUPACName = iodine(I) chloride | OtherNames = iodine chloride | Section1 = {{Chembox Identifiers | SMILES = ICl | CASNo = 7790-99-0 | RTECS = }} | Section2 = {{Chembox Properties | Formula = ICl | MolarMass = 162.35 g/mol | Appearance = red to brown liquid | Density = 3.10 g/cm<sup>3</sup> | Solubility = [[hydrolysis]] | Solvent = other solvents | SolubleOther = [[carbon disulfide]]<br /> [[acetic acid]]<br /> [[pyridine]] | MeltingPt = 27°C (α-form) | BoilingPt = 97.4°C (370.6 K) }} | Section3 = {{Chembox Structure | CrystalStruct = <!-- e.g. [[triclinic]], [[monoclinic]], [[orthorhombic]], [[hexagonal]], [[rhombohedral|trigonal]], [[tetragonal]], [[cubic]], and mention "close packed" or similar. You may also cite what class it belongs to, e.g. [[Cadmium chloride#Crystal_structure|CdCl<sub>2</sub>]] --> | Dipole = }} | Section7 = {{Chembox Hazards | ExternalMSDS = [http://www.jtbaker.com/msds/englishhtml/i2760.htm External MSDS] | MainHazards = corrosive | RPhrases = | SPhrases = }} | Section8 = {{Chembox Related | Function = interhalogen compounds | OtherFunctn = [[Chlorine monofluoride]], [[bromine monochloride]], [[iodine monobromide]] }} }} '''Iodine monochloride''' is the [[chemical compound]] with the formula ICl. It is a red-brown compound that melts near room temperature. Because of the difference in the electronegativity of [[iodine]] and [[chlorine]], ICl is highly [[chemical polarity|polar]] and behaves as a source of “I<sup>+</sup>.” Preparation of iodine monochloride entails simply combining the halogens in a 1:1 molar ratio, according to the equation :I<sub>2</sub> + Cl<sub>2</sub> → 2 ICl When chlorine gas is passed through iodine crystals, one observes the brown vapor of iodine monochloride. Dark brown iodine monochloride liquid is collected. Excess chlorine converts iodine monochloride into [[iodine trichloride]] in a reversible reaction: :ICl + Cl<sub>2</sub> → ICl<sub>3</sub> ==Polymorphs== ICl has two [[polymorphism (materials science)|polymorphs]]; α-ICl which exists as black needles (red by transmitted light) with a [[melting point]] of 27.2 °C, and β-ICl which exists as black platelets (red-brown by transmitted light) with a melting point 13.9 °C.<ref name=Bris>Brisbois, R. G.; Wanke, R. A.; Stubbs, K. A.; Stick, R. V. “Iodine Monochloride” Encyclopedia of Reagents for Organic Synthesis, 2004 John Wiley & Sons. DOI: 10.1002/047084289X.ri014</ref> ==Uses== ICl is a useful reagent in [[organic synthesis]].<ref name=Bris/> It is used as a source of [[electrophilic]] iodine in the synthesis of certain [[aromatic]] iodides.<ref>{{OrgSynth | author = Wallingford, V. H.; Krüger, P. A. | title = 5-Iodo-anthranilic Acid | collvol = 2 | collvolpages = 349 | year = 1943 | prep = cv2p0349}}</ref> It also cleaves C-Si bonds. ICl will also add to the [[double bond]] in [[alkene]]s to give chloro-iodo [[alkane]]s. :RCH=CHR’ + ICl → RCH(I)-CH(Cl)R’ When such reactions are conducted in the presence of [[sodium azide]], the iodo-azide RCH(I)-CH(N<sub>3</sub>)R’ is obtained.<ref>{{OrgSynth | author = Padwa, A.; Blacklock, T.; Tremper, A. | title = 3-Phenyl-2H-Azirine-2-carboxaldehyde | collvol = 6 | collvolpages = 893 | prep = cv6p0893}}</ref> ==References== <references/> [[Category:Iodine compounds]] [[Category:Chlorides]] [[Category:Interhalogen compounds]] [[zh:一氯化碘]]