3,5-diiodophenol
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| General | ||||||||||
| Surname | 3,5-diiodophenol | |||||||||
| Molecular formula | C 6 H 4 I 2 O | |||||||||
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| properties | ||||||||||
| Molar mass | 345.9 g mol −1 | |||||||||
| Physical state |
firmly |
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| Melting point |
104 ° C |
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| pK s value |
8.10 (25 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
3,5-Diiodophenol is a chemical compound that belongs to both the phenols and the halogen aromatic compounds .
presentation
The multi-stage synthesis of 3,5-diiodophenol starts from p-nitroaniline , which is iodinated with iodine chloride to give 2,6-diiodo-4-nitroaniline . Deamination then leads to 3,5-diiodonitrobenzene , which is converted into 3,5-diiodaniline by reducing the amino group . Boiling the diazonium salt finally leads to the desired product.
Another possible synthesis is based on 3,5-dinitroanisole , which is first reduced with acetic acid , platinum (IV) oxide and hydrogen to 3,5-diaminoanisole . This is diazotized with sodium nitrite , sulfuric acid and acetic acid and converted into 3,5-diiodanisole with sodium iodide and elemental iodine . The desired compound is finally formed by ether cleavage with hydrogen iodide in acetic acid.
properties
Esterification with acetic anhydride yields the acetate, which melts at 79 ° C.
The methyl ether can be produced by methylation with dimethyl sulfate and is also known under the common name 3,5-diiodanisole. Its melting point is 85 ° C.
Individual evidence
- ^ A b c d John B. Buckingham: Dictionary of Organic Compounds . 6th edition. tape 8 . Chapman & Hall, London 1996, ISBN 0-412-54090-8 , pp. 2499 .
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ PD Bolton, FM Hall, J. Kudrynski: "Additive substitent effects on the ionization of meta-substituted phenols", in: Australian Journal of Chemistry , 1968 , 21 (6), pp. 1541-1549; doi: 10.1071 / CH9681541 .
- ↑ James E. Redman, Ph.D. Thesis, chap. 3-3: "Porphyrins for SAMs"; Full text ( memento of March 2, 2010 in the Internet Archive ).