benzene-1,3,5-triol

• ChemBase ID: 89823
• Molecular Formular: C6H6O3
• Molecular Mass: 126.11004
• Monoisotopic Mass: 126.03169405
• SMILES: Oc1cc(cc(c1)O)O
• Canonical SMILES: Oc1cc(O)cc(c1)O
• InChI: InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
• InChIKey: QCDYQQDYXPDABM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzene-1,3,5-triol
• IUPAC Traditional name: phloroglucinol
• Synonyms: 1,3,5-Benzenetriol, anhydrous; Phloroglucinol, anhydrous; 1,3,5-Benzenetriol; Benzene-s-triol; Dilospan S; NSC 1572; Phloroglucin; Spasfon-Lyoc; sym-Trihydroxybenzene; Phloroglucinol; Benzene-1,3,5-triol; 1,3,5-TRIHYDROXYBENZENE; 1,3,5-Trihydroxybenzene; PHLOROGLUCINOL; phloroglucine; 1,3,5-benzenetrioe; or cyclohexane-1,3,5-trione; Phloroglucinol; 无水间苯三酚; 1,3,5-三羟苯; 间苯三酚

Database IDs

• CAS Number: 108-73-6
• EC Number: 203-611-2
• MDL Number: MFCD00002286
• Beilstein Number: 1341907
• Merck Index: 147328
• PubChem SID: 24887444; 24898169; 162076679; 24898417
• PubChem CID: 359
• CHEBI ID: 16204
• ATC CODE: A03AX12
• CHEMBL: 473159
• Chemspider ID: 352
• Unique Ingredient Identifier: DHD7FFG6YS
• Wikipedia Title: Phloroglucinol

CALCULATED PROPERTIES

• Acid pKa: 9.126325
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.0624478
• LogD (pH = 7.4): 1.0545149
• Log P: 1.0625498
• Molar Refractivity: 32.0007 cm^3
• Polarizability: 12.179353 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 g/100 mL in water; Methanol
• Apperance: white solid; White to Off-White Solid
• Melting Point: 215-220 °C; 215-220°C; 215-220°C; 217.9-218.6°C; 217°C; 218°C; 218–220 °C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: Harmful/Irritant/Mutagenic/Teratogenic/Light Sensitive/Hygroscopic; Light Sensitive & Hygroscopic
• RTECS: SY1050000; UX1050000
• European Hazard Symbols: Toxic (T); Irritant (Xi); Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 36/37/38; 63-68; R:25
• Safety Statements: 26-37; 36/37; S:28-36/37/39-45-53
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H341-H361
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P281
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (HPLC); 98%
• Suitability: plant cell culture tested
• Impurities: ≤2% water; diresorcin, none detected
• Empirical Formula (Hill Notation): C6H6O3

DETAILS

MP Biomedicals - 02151848

Anhydrous

MP Biomedicals - 05217839

MP Biomedicals Rare Chemical collection

Sigma Aldrich - P1178

General description
Phloroglucinol is a trihydroxybenzene with antithrombotic, profibrinolytic, antimicrobial, antimalarial, cancer chemopreventive, anti-HIV and anti-leishmanial activities. Phloroglucinol (PG) is a biosynthetic precursor of the 2,4-diacetylphloroglucinol (DAPG) an antibiotic against soil-borne diseases. Phloroglucinol is a useful intermediate because it is polyfunctional.

Sigma Aldrich - 79330

Packaging
25, 100 g in poly bottle

Toronto Research Chemicals - P340000

Antispasmodic.

REFERENCES

• Mizuuchi, Y., et al.: Biol. Pharm. Bull., 31, 2205 (2008)
• Li, Y., et al.: Bioorg. Med. Chem., 17, 1963 (2008)
• da Silva, S., et al.: Eur. J. Med. Chem., 44, 312 (2008)
• Zhu, Q., et al.: J. Agric. Food Chem., 57, 1065 (2008)
• Reacts with mono- or dimethylamine in DMF-water, with displacement of one of the OH groups, to give 5-aminoresorcinols: Helv. Chim. Acta, 56, 510 (1973).
• The electron-rich nucleus undergoes acylation with nitriles under mild Lewis acid catalysis, to give ketones (Houben-Hoesch reaction).
• Selective monobromination cannot be achieved conventionally. For bromination-debromination protocols for the preparation of the mono- and di-brominated derivatives, see: Can. J. Chem., 67, 335 (1989).