Chlorination of iodophenols. V. m-Iodophenol was written by Buchan, Samuel;McCombie, Hamilton. And the article was included in Journal of the Chemical Society in 1932.Application of 289039-26-5 This article mentions the following:
M-IC6H4OH (I) in CCl4 and Cl give a series of unstable iododichlorides and ring-substituted decomposition products very similar to those obtained from the p- and o-isomers (C. A. 25, 1504). I gives an acetate, m. 38°; the iododichloride, m. 91-2° (decomposition), decomposes over 7 days. The benzyl ether m. 52°; iododichloride, m. 70° (decomposition), decomposes over 2 days. Benzoate, m. 72-3°; iododichloride, m. 106° (decomposition), stable. p-Toluenesulfonate, m. 60-1°; iododichloride, m. 97-9° (decomposition), stable. Et carbonate, b11, 163-4°; iododichloride, m. 79-80° (decomposition), stable for 4 months. Iodophenyl carbonate, m. 141°; bis(iododichloride), m. 115° (decomposition), stable. Me ether, b14 123°; iododichloride, m. 74° (decomposition), very unstable. Et ether, b15 133-4°, iododichloride, m. 64° (decomposition), unstable. Allyl ether, b11 154-6°. Dibromopropyl ether, oily; iododichloride, m. 78° (decomposition), decomposes overnight. Phenylcarbamate, m. 138°; iododichloride, m. 120° (decomposition), moderately stable. 3-Iododiphenyl ether, b14 185°; iododichloride, m. 58°, decomposes over 2 days. ω-3′-Iodophenoxyacetophenone, m. 104°; iododichloride, m. 94°, decomposes over a period of several days. I in CCl4 and Cl give an iododichloride, which gives with KI and AcOH 6-chloro-3-iodophenol, m. 56°; its acetate b11 149° (iododichloride, m. 89° (decomposition), decomposes after 2 days); the benzyl ether b11 250-60° (iododichloride, m. 72° (decomposition), decomposes after 2 days). 2,4-I(O2N)C6H3NH2 gives 4-chloro-3-iodophenol, m. 78°. Chlorination of I in CCl4 at 0° gives an iododichloride, m. 59°, which decomposes to give 4,6-dichloro-3-iodophenol (II), m. 104°; its iododichloride, m. 68-9° (decomposition), decomposes to give 2,4,6-trichloro-3-iodophenol (III), m. 104°. II yields an acetate, m. 95° (iododichloride, m. 104° (decomposition), stable). Benzyl ether, m. 82° (iododichloride, m. 86° (decomposition), decomposes after several days). III gives a benzyl ether, m. 80-1°). Neither III nor its derivatives yield iododichlorides. Chlorination of I at 60-70° in CCl4 gives almost pure III; further chlorination gives the tetra-Cl derivative and Cl5C6OH. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-iodophenol (cas: 289039-26-5Application of 289039-26-5).
2-Chloro-5-iodophenol (cas: 289039-26-5) belongs to iodide derivatives. Organic iodides are organic compounds containing a carbon-iodine (C-I) bond. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. The C–I bond is the weakest of the carbon–halogen bonds. These bond strengths correlate with the electronegativity of the halogen, decreasing in the order F > Cl > Br > I.Application of 289039-26-5
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com