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phloroglucinol
Phloroglucinol structure.png
Phloroglucinol-3D.png
IUPAC name
Other names phloroglucine, 1,3,5-trihydroxybenzene, 1,3,5-benzenetriol, or cyclohexane-1,3,5-trione
Identifiers
CAS number 108-73-6 Yes check.svgY
RTECS number UX1050000
SMILES
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)
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Tautomeric equilibrium

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]

Phlorosynth.png

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

References

  1. ^ 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.
  2. ^ C. Michael Hogan. 2008. Coastal Woodfern (Dryopteris arguta}, GlobalTwitcher, ed. N. Stromberg
  3. ^ "Intermediate Pharmaceutical Ingredients - Flopropione". Univar Canada. http://www.univarcanada.com/pdfdoc/pharmaceutical/Intermediates.pdf. Retrieved 24 April 2009.  
  4. ^ "Synthesis of trinitrophloroglucinol". The United States Patent and Trademark Office. 1984. http://www.freepatentsonline.com/4434304.html. Retrieved 24 April 2009.  
  5. ^ "PHLOROGLUCINOL". Biam. 1999. http://www.biam2.org/www/Sub2438.html. Retrieved 24 April 2009.   (in French)
  6. ^ "Phloroglucinol Summary Report". EMEA. http://www.emea.europa.eu/pdfs/vet/mrls/004695en.pdf. Retrieved 24 April 2009.  
  7. ^ 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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