Iodine monochloride

Iodine monochloride

Chembox new
Name = Iodine monochloride
ImageFile = Iodine-monochloride-2D.png ImageName = Iodine monochloride
ImageFile1 = Iodine-monochloride-3D-vdW.png 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/cm3
Solubility = hydrolysis
Solvent = other solvents
SolubleOther = carbon disulfide
acetic acid
pyridine
MeltingPt = 27°C (α-form)
BoilingPt = 97.4°C (370.6 K)
Section3 = Chembox Structure
CrystalStruct =
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 polar and behaves as a source of “I+.”

Preparation of iodine monochloride entails simply combining the halogens in a 1:1 molar ratio, according to the equation:I2 + Cl2 → 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 + Cl2 → ICl3

Polymorphs

ICl has two 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.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]

Uses

ICl is a useful reagent in organic synthesis. It is used as a source of electrophilic iodine in the synthesis of certain aromatic iodides. [OrgSynth | author = Wallingford, V. H.; Krüger, P. A. | title = 5-Iodo-anthranilic Acid | collvol = 2 | collvolpages = 349 | year = 1943 | prep = cv2p0349] It also cleaves C-Si bonds.

ICl will also add to the double bond in alkenes to give chloro-iodo alkanes.: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(N3)R’ is obtained. [OrgSynth | author = Padwa, A.; Blacklock, T.; Tremper, A. | title = 3-Phenyl-2H-Azirine-2-carboxaldehyde | collvol = 6 | collvolpages = 893 | prep = cv6p0893]

References


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