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Reagent for pentoses, pentosans and aldehydes. Used as a bone decalcifier in microscopy specimens.Phloroglucinol is mainly used as a coupling agent in printing. It is an active component of Tollens reagent and Gunzburg reagent used to test pentoses and hydrochloric acid in gastric juice respectively. In analytical chemistry, it is used to study condensed tannins by means of depolymerization. It is also involved in the synthesis of 2,4,6-triamino-1,3,5- trinitrobenzene, trinitrophloroglucinol and pharmaceuticals like flopropione .
Reacts with mono- or dimethylamine in DMF-water, with displacement of one of the OH groups, to give 5-aminoresorcinols: Helv. Chim. Acta, 56, 510 (1973).
The electron-rich nucleus undergoes acylation with nitriles under mild Lewis acid catalysis, to give ketones (Houben-Hoesch reaction).
Selective monobromination cannot be achieved conventionally. For bromination-debromination protocols for the preparation of the mono- and di-brominated derivatives, see: Can. J. Chem., 67, 335 (1989).
Dubey, R.; Desiraju, G. R. Combinatorial Crystal Synthesis: Structural Landscape of Phloroglucinol: 1, 2-bis (4-pyridyl) ethylene and Phloroglucinol: Phenazine. Angew. Chem. Int. Ed. 2014, 53 (48), 13178-13182.
Ghimbeu, C. M.; Vidal, L.; Delmotte, L.; Le Meins, J. M.; Vix-Guterl, C. Catalyst-free soft-template synthesis of ordered mesoporous carbon tailored using phloroglucinol/glyoxylic acid environmentally friendly precursors. Green Chem. 2014, 16 (6), 3079-3088.
Gefahrenhinweise (EU): H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.