2-iodoxybenzoic acid
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| Surname | 2-iodoxybenzoic acid | |||||||||||||||
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| Molecular formula | C 7 H 5 IO 4 | |||||||||||||||
| Brief description |
white solid |
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| properties | ||||||||||||||||
| Molar mass | 280.02 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| Melting point |
233 ° C (decomposition) |
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| solubility |
almost insoluble in most organic solvents |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
2-Iodoxybenzoic acid is a chemical compound from the group of hypervalent iodine compounds .
Extraction and presentation
2-Iodoxybenzoic acid can be obtained by the Dess-Martin process by reacting 2-iodobenzoic acid with sulfuric acid and potassium bromate at 55 ° C. The compound was first synthesized in 1893 by Christoph Hartmann and Victor Meyer by reacting the oxidation of 2-iodobenzoic acid with potassium permanganate . The chemical structure was elucidated by FR Greenbaum in 1936.
properties
2-Iodoxybenzoic acid is a white crystalline solid with an intensely sour taste that is insoluble in most organic solvents . It decomposes explosively at 233 ° C. The technical product is stabilized with benzoic acid on the market.
Dry, unstabilized IBX decomposes under the influence of light and air, which shows itself in a discoloration from colorless-gray to light pink-orange.
The compound is classified as explosive according to the SprengG and was assigned to substance group C.
use
2-Iodoxybenzoic acid is used as an oxidizing agent from primary and secondary alcohols to aldehydes and ketones and from amines to imines .
It is also used for other chemical reactions, for example for the elimination of VX warfare agents and for dehydration to enones, for oxygenation and for other oxidative processes.
See also
Individual evidence
- ↑ a b c d e uni-heidelberg.de: New applications of IBX , accessed on September 12, 2015.
- ↑ a b c d e data sheet 2-Iodoxybenzoic acid, contains stabilizer, 45 wt.% (IBX) from Sigma-Aldrich , accessed on September 12, 2015 ( PDF ).
- ↑ WLF Armarego, Christina Li Lin Chai: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2013, ISBN 0-12-382161-4 , pp. 998 ( limited preview in Google Book search).
- ↑ Announcement of the new findings made by BAM since 1987 in accordance with § 2 SprengG - notification of assessment No. 470 of November 25, 2009 pdf link .
- ↑ KC Nicolaou, CJN Mathison, T. Montagnon: New Reactions of IBX: Oxidation of Nitrogen‐ and Sulfur ‐ Containing Substrates to Afford Useful Synthetic Intermediates In: Angew. Chem. 115, 2003, pp. 4211-4216, doi : 10.1002 / anie.200352076 .
- ↑ Alexander showerk, Stefan F. Kirsch: 2-iodoxybenzoic acid - a simple oxidizing agent with a variety of possible uses. In: Angewandte Chemie. 123, 2011, p. 1562, doi : 10.1002 / anie.201000873 .