| phloroglucinol | |
|---|---|
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| IUPAC name |
Benzene-1,3,5-triol
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| Other names | phloroglucine, 1,3,5-trihydroxybenzene, 1,3,5-benzenetriol, or cyclohexane-1,3,5-trione |
| Identifiers | |
| CAS number | 108-73-6  |
| RTECS number | UX1050000 |
| SMILES |
Oc1c(O)cccc1
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| Properties | |
| Molecular formula | C6H6O3 |
| Molar mass | 126.11 g/mol |
| Appearance | white solid |
| Melting point |
218-220 °C, 271 K, -146 °F |
| Solubility in water | 1 g/100 mL |
| Hazards | |
| EU classification | Harmful (Xn) |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Phloroglucinol is an organic compound that is used in the synthesis of pharmaceuticals and explosives. This molecule exists in two forms, or tautomers, 1,3,5-trihydroxybenzene, which has phenol-like, and 1,3,5-cyclohexanetrione (phloroglucin), which has ketone-like character. These two tautomers are in equilibrium. Phloroglucinol is a useful intermediate because it is polyfunctional.
From water, phloroglucinol crystallizes as the dihydrate, which has a melting point of 116-117 °C, but the anhydrous form melts much higher, at 218-220 °C. It does not boil intact, but it does sublime.
Contents |
Isolation, synthesis, and reactions
Phloroglucinol was originally isolated from bark of fruit trees. It is synthesized via a number of processes, but representative is the following route from trinitrobenzene:[1]
The synthesis is noteworthy because ordinary aniline derivatives are unreactive toward hydroxide. Because the triaminobenzene also exists as its imine tautomer, it is susceptible to hydrolysis.
The compound behaves like a ketone in its reaction with hydroxylamine, forming the tris(oxime). But it behaves also like a triphenol (Ka1 = 3.56 × 10–9, Ka2 1.32×10–9), as the three hydroxyl groups can be methylated to give 1,3,5-trimethoxybenzene.[1]
Natural occurrence
Phloroglucinols occur naturally in certain plant species. For example, they (and sometimes their acyl dervatives) are present in the fronds of the Coastal woodfern, Dryopteris arguta.[2]
Metabolism
Phloretin hydrolase uses phloretin and H2O to produce phloretate and phloroglucinol.
Applications
Phloroglucinol is mainly used as a coupling agent in printing. It links diazo dyes to give a fast black.
It is useful for the industrial synthesis of pharmaceuticals[3] and explosives.[4] It is also used as a treatment for gastrointestinal disorders.[5] [6] [7]
See also
- Pyrogallol (1,2,3-trihydroxybenzene)
References
- ^ a b Helmut Fiege, Heinz-Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans-Josef Buysch, Dorothea Garbe, Wilfried Paulus "Phenol Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Wienheim, 2005. DOI: 10.1002/14356007.a19_313. Published online: 15 June, 2002.
- ^ C. Michael Hogan. 2008. Coastal Woodfern (Dryopteris arguta}, GlobalTwitcher, ed. N. Stromberg
- ^ "Intermediate Pharmaceutical Ingredients - Flopropione". Univar Canada. http://www.univarcanada.com/pdfdoc/pharmaceutical/Intermediates.pdf. Retrieved 24 April 2009.
- ^ "Synthesis of trinitrophloroglucinol". The United States Patent and Trademark Office. 1984. http://www.freepatentsonline.com/4434304.html. Retrieved 24 April 2009.
- ^ "PHLOROGLUCINOL". Biam. 1999. http://www.biam2.org/www/Sub2438.html. Retrieved 24 April 2009. (in French)
- ^ "Phloroglucinol Summary Report". EMEA. http://www.emea.europa.eu/pdfs/vet/mrls/004695en.pdf. Retrieved 24 April 2009.
- ^ Chassany O et al. (2007). "Acute exacerbation of pain in irritable bowel syndrome: efficacy of phloroglucinol/trimethylphloroglucinol. A randomized, double-blind, placebo-controlled study.". Alimentary pharmacology & therapeutics 1 (25): 1115–23. PubMed
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