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Saturday, February 19, 2011


CAS number 108-73-6 YesY
PubChem 359
RTECS number UX1050000
Molecular formula C6H6O3
Molar mass 126.11 g/mol
Exact mass 126.031694
Appearance white solid
Melting point 218-220 °C
Solubility in water 1 g/100 mL
EU classification Harmful (Xn)
 YesY(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 a benzenetriol. It 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.


  • 1 Isolation, synthesis, and reactions
  • 2 Natural occurrence
  • 3 Metabolism
  • 4 Applications

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] Brown algae also produce phloroglucinol derivatives[3][4] known as phlorotannins.[5]


Phloretin hydrolase uses phloretin and water to produce phloretate and phloroglucinol.


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[6] and explosives.[7] It is also used as a treatment for gallstones, spasmodic pain and other related gastrointestinal disorders.[8][9][10] It has a non-specific spasmolytic action on the vessels, bronchi, intestine, ureters and gall bladder, and is used for treating disorders of these organs.

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