Phloroglucinol

Phloroglucinol

Names
IUPAC name Benzene-1,3,5-triol
Other names phloroglucine, 1,3,5-trihydroxybenzene, 1,3,5-benzenetriol, or cyclohexane-1,3,5-trione
Identifiers
CAS Number	108-73-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16204 Y
ChEMBL	ChEMBL473159 Y
ChemSpider	352 Y
ECHA InfoCard	100.003.284
EC Number	203-611-2
PubChem	359
RTECS number	UX1050000
UNII	DHD7FFG6YS Y
InChI InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H Y Key: QCDYQQDYXPDABM-UHFFFAOYSA-N Y InChI=1/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H Key: QCDYQQDYXPDABM-UHFFFAOYAF
SMILES c1c(cc(cc1O)O)O
Properties
Chemical formula	C6H6O3
Molar mass	126.11 g/mol
Appearance	colorless to beige solid
Melting point	219 °C (426 °F; 492 K)
Solubility in water	1 g/100 mL
Solubility	soluble in diethyl ether, ethanol, pyridine
Acidity (pKa)	8.45
Magnetic susceptibility (χ)	-73.4·10−6 cm3/mol
Pharmacology
ATC code	A03AX12 (WHO)
Hazards
EU classification (DSD)	Harmful (Xn)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	5 g/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Phloroglucinol is an organic compound that is used in the synthesis of pharmaceuticals and explosives. It is a phenol derivative with antispasmodic properties that is used primarily as a laboratory reagent.

Austrian chemist Heinrich Hlasiwetz (1825–1875) is remembered for his chemical analysis of phloroglucinol.

Phloroglucinol is also generally found in the flavonoid ring A substitution pattern.

Phloroglucinol (1,3,5-benzenetriol) is a benzenetriol, found along with two isomers, hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol).

Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, but they cannot be by any scientifically-accepted definition.

This molecule has a unique symmetric arene substitution pattern of a trisubstituted benzene. It is a type of enol and exists in two forms, or tautomers; 1,3,5-trihydroxybenzene, which has phenol-like character, and 1,3,5-cyclohexanetrione (phloroglucin), which has ketone-like character. These two tautomers are in equilibrium.