Overview
Phloroglucinol is a benzenetriol derivative with three hydroxyl groups symmetrically arranged on a benzene ring. First isolated in 1841 by Austrian chemist Heinrich Hlasiwetz, it occurs naturally in some plants and marine organisms. The compound exists in equilibrium with its tautomeric form, cyclohexane-1,3,5-trione, though the aromatic form predominates under standard conditions. As a key intermediate in organic synthesis, phloroglucinol's reactivity stems from its phenolic hydroxyl groups and aromatic ring. Its unique structure allows participation in condensation, complexation, and substitution reactions. The global market for this chemical is driven by pharmaceutical applications, particularly in Europe and Asia where it's formulated into antispasmodic medications.
Physical and Chemical Properties
Phloroglucinol crystallizes as colorless needles or plates with a faint phenolic odor. It exhibits moderate water solubility due to hydrogen bonding, increasing with temperature. The compound shows characteristic phenolic chemistry: forming salts with bases, undergoing electrophilic substitution at the 2, 4, and 6 positions, and acting as a weak acid (pKa1~8.5). Notably, it reduces Fehling's solution and forms colored complexes with ferric chloride (violet). When heated above 200°C, gradual decomposition occurs with carbonization. The tautomeric equilibrium with cyclohexane-1,3,5-trione becomes significant in alkaline solutions, where the keto form predominates. This dual reactivity makes it valuable for synthesizing heterocyclic compounds and coordinating with metal ions.
Main Applications
In pharmaceuticals, phloroglucinol is the active ingredient in antispasmodic drugs like Spasfon®, prescribed for gastrointestinal and urinary tract disorders. Its mechanism involves calcium channel blockade in smooth muscles. The compound also serves as a building block for flavonoid synthesis and appears in some dental adhesives. Industrially, it's used to manufacture azo dyes, epoxy resins, and explosives (e.g., phloroglucinol trinitrate). Analytical chemists employ it for detecting aromatic aldehydes (Kowarski test) and quantifying flavonoids via the Porter assay. Emerging applications include nanoparticle synthesis and as a crosslinker for biodegradable polymers. In histology, it helps stain lignin in plant tissues.
Safety and Storage
As a mild irritant, phloroglucinol requires handling with nitrile gloves and eye protection. Inhalation of dust may cause respiratory irritation, necessitating local exhaust ventilation during large-scale processing. The compound isn't classified as flammable but may decompose at high temperatures, releasing phenolic vapors. For long-term storage, maintain in original packaging at 15-25°C with <60% relative humidity. Incompatible materials include strong oxidizers (risk of exothermic reactions) and acid chlorides. Shelf life typically exceeds 2 years when properly stored. Spills should be contained with inert absorbents and disposed as hazardous organic waste according to local regulations.
B2B Procurement Guide
Industrial buyers should specify technical (98%+) or pharmaceutical grade (99.5%+, meets EP/USP standards) based on application needs. Key quality indicators include melting point range (217-221°C), residual solvent levels, and heavy metal content. Bulk shipments typically come in 25kg fiber drums with polyethylene liners. Chinese manufacturers dominate production, with capacity concentrated in Jiangsu and Shandong provinces. Due to pharmaceutical use, ensure suppliers provide certificates of analysis (CoA), GMP compliance documentation, and full traceability. Spot prices fluctuate with benzene (raw material) costs. For research quantities, Sigma-Aldrich and TCI America offer small packaging with purity up to 99.9%.
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