Iodine monochloride

Iodine monochloride, formed when iodine reacts with the iodate(V) ion in the presence of an excess of concentrated hydrochloric acid. 

Amino-3 5-diiodobenzoic acid. In a 2 litre beaker, provided with a mechanical stirrer, dissolve 10 g. of pure p-aminobenzoic acid, m.p. 192° (Section IX,5) in 450 ml. of warm (75°) 12 -5 per cent, hydrochloric acid. Add a solution of 48 g. of iodine monochloride (1) in 40 ml. of 25 per cent, hydrochloric acid and stir the mixture for one minute during this time a yellow precipitate commences to appear. Dilute the reaction mixtiue with 1 litre of water whereupon a copious precipitate is deposited. Raise the temperature of the well-stirred mixture gradually and maintain it at 90° for 15 minutes. Allow to cool to room tempera-tiue, filter, wash thoroughly with water and dry in the air the yield of crude acid is 24 g. Purify the product by dissolving it in dilute sodium hydroxide solution and precipitate with dilute hydrochloric acid the yield of air-dried 4-amino-3 5-diiodobenzoic acid, m.p. >350°, is 23 g. 

Iodine monochlorlde may be prepared as follows. Pass dry chlorine into 127 g. of iodine contained in a 125 ml. distilling flask until the weight has increased by 34-6 g. The chlorine should be led in at or below the surface of the iodine whilst the flask is gently shaken it is essential to have an excess of iodine. Distil the iodine chloride in an ordinary distillation apparatus use a filter flask, protected from atmospheric moisture by a calcium chloride (or cotton wool) guard tube, as a receiver. Collect the fraction b.p. 97-105° the jdeld is 140 g. Preserve the iodine monochloride in a dry, glass-stoppered bottle. 

Since iodine monochloride attacks cork and rubber, the use of an all-glass apparatus is recommended. If it should come into contact with the skin, an elective antidote is dilute hydrochloric acid (1 1). 

Iodine monochloride Aluminum foil, organic matter, metal sulfides, phosphorus, potassium, rubber, sodium... 

The iodination reaction can also be conducted with iodine monochloride in the presence of sodium acetate (240) or iodine in the presence of water or methanolic sodium acetate (241). Under these mild conditions functionalized alkenes can be transformed into the corresponding iodides. AppHcation of B-alkyl-9-BBN derivatives in the chlorination and dark bromination reactions allows better utilization of alkyl groups (235,242). An indirect stereoselective procedure for the conversion of alkynes into (H)-1-ha1o-1-alkenes is based on the mercuration reaction of boronic acids followed by in situ bromination or iodination of the intermediate mercuric salts (243). 

However, in strong hydrochloric acid, these reagents, as weU as iodic acid, oxidize iodine to iodine monochloride or to the ICl ion. 

Iodine monochloride [7790-99-0] ICl, mol wt 162.38, 78.16% I, is a black crystalline soHd or a reddish brown Hquid. SoHd ICl exists ia two crystalline modifications the a-form, as stable mby-red needles, d = 3.86 g/mL and mp 27.3°C and as metastable brownish red platelets, d = 3.66 g/mL, mp 13.9°C and bp 100°C (dec). Iodine monochloride is used as a halogenation catalyst and as an analytical reagent (Wij s solution) to determine iodine values of fats and oils (see Fats and fatty oils). ICl is prepared by direct reaction of iodine and Hquid chlorine. Aqueous solutions ate obtained by treating a suspension of iodine ia moderately strong hydrochloric acid with chlorine gas or iodic acid (118,119). 

The aHphatic iodine derivatives are usually prepared by reaction of an alcohol with hydroiodic acid or phosphoms trHodide by reaction of iodine, an alcohol, and red phosphoms addition of iodine monochloride, monobromide, or iodine to an olefin replacement reaction by heating the chlorine or bromine compound with an alkaH iodide ia a suitable solvent and the reaction of triphenyl phosphite with methyl iodide and an alcohol. The aromatic iodine derivatives are prepared by reacting iodine and the aromatic system with oxidising agents such as nitric acid, filming sulfuric acid, or mercuric oxide. 

Pyridazines form complexes with iodine, iodine monochloride, bromine, nickel(II) ethyl xanthate, iron carbonyls, iron carbonyl and triphenylphosphine, boron trihalides, silver salts, mercury(I) salts, iridium and ruthenium salts, chromium carbonyl and transition metals, and pentammine complexes of osmium(II) and osmium(III) (79ACS(A)125). Pyridazine N- oxide and its methyl and phenyl substituted derivatives form copper complexes (78TL1979). 

Iodine monochloride, purchased from J. T. Baker Chemical Company, was used without further purification. 

Molecular iodine is not a very powerful halogenating agent. Only very reactive aromatics such as anilines or phenolate anions are reactive toward iodine. Iodine monochloride can be used as an iodinating agent. The greater electronegativity of the... 

Bromine trifluoride and pentafluoride Chlorine trifluoride Iodine monochloride... 

Interhalogen compounds such as iodine monochloride have been added to fluoroalkyl-substituted alkenes. The observed unidirectional regiochemistry can be explained by the polarity ot the double bond [14] (equation 7)... 

Iodine monochloride adds unidirectionally to perfluoropropene-2-ol to form a chlorohydrin, which easily dehydrochlonnates to yield lodopentafluoroacetone [/5] (equation 8). 

Like simple elemental halogens, iodine monochloride reacts with conjugated fluorodienes to yield mostly 1,4-addition products. These bidirectional reactions lead to mixtures of regioisomers, as shown in Table 5 [//]. 

The reaction of 2H-nonatluoro-2-methylpropane with iodine monochloride in sulfolane in the presence of potassium fluoride produces 2-chlorononafluoro-2-methylpropane in 92% yield at 50% conversion [2d]. 

Chlor-jod, n. iodine chloride, specif, iodine monochloride, -kali, n. chloride of potash (potassium hypochlorite) potassium chloride. -kalilOsung, /. Pharm.) solution of chlorinated potassa, Javelle water, -kalium, n. potassium chloride. 

C) Preparation of 0-(3-Amino-2,4,6-Triiodophenylj-a-Ethylpropionic Acid A solution of 5.0 g of m-amino-o -ethylhydrocinnamic acid in 100 cc of water containing 5 cc of concentrated hydrochloric acid is added over a period of A hour to a stirred solution of 3.2 cc of iodine monochloride in 25 cc of water and 25 cc of concentrated hydrochloric acid... 

As an illustration, in the iodine monochloride (I — Cl) molecule, the electron pair being shared remains closer to the more electronegative Cl atom. This creates fractional negative and positive charges, referred to as formal charges, on the Cl and I atoms, respectively, as illustrated below ... 

Aromatic iodination can be carried out with a number of reagents, including iodine monochloride, 1C1. What is the direction of polarization of IC1 Propose a mechanism for the iodination of an aromatic ring with 1C). 

In more strongly acid solutions (3-6M hydrochloric acid) reduction occurs to iodine monochloride, and it is under these conditions that it is most widely used.20 21... 

In hydrochloric acid solution, iodine monochloride forms a stable complex ion with chloride ion ... 

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