1H-indol-5-ol

• ChemBase ID: 15934
• Molecular Formular: C8H7NO
• Molecular Mass: 133.14728
• Monoisotopic Mass: 133.05276385
• SMILES: c1(O)cc2c(cc1)[nH]cc2
• Canonical SMILES: Oc1ccc2c(c1)cc[nH]2
• InChI: InChI=1S/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H
• InChIKey: LMIQERWZRIFWNZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indol-5-ol
• IUPAC Traditional name: 5-hydroxyindol
• Synonyms: 5-Hydroxy-indole; 5-Hydroxyindole; 1H-Indol-5-ol; 5-Hydroxy-1H-indole; NSC 87503; 5-Hydroxyindole; 5-Hydroxyindole; 5-Indolol; Indol-5-ol; Hydroxy-5-indole; 1H-indol-5-ol; 5-Hydroxy-1H-indole; 5-羟基吲哚; 5-羟基苯并吡咯; 5-羟基苯并吡咯; 5-羟基吲哚

Database IDs

• CAS Number: 1953-54-4
• EC Number: 217-782-6
• MDL Number: MFCD00005677
• Beilstein Number: 112349
• PubChem SID: 24895561; 160979241
• PubChem CID: 16054

CALCULATED PROPERTIES

• Log P: 1.7684425
• Molar Refractivity: 39.1254 cm^3
• Polarizability: 16.175694 Å^3
• Polar Surface Area: 36.02 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 9.572356
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): 1.7684059
• LogD (pH = 7.4): 1.76555

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Brown Solid
• Melting Point: 100-110°C; 106-108 °C(lit.); 106-108°C; 106-111°C; 106-111°C; 107-108°C
• Hydrophobicity(logP): 1.465

Safety Information

• Storage Condition: 2-8°C, Protect from light; Refrigerator
• Storage Warning: IRRITANT, KEEP COLD; Irritant/Light Sensitive/Store under Argon/Keep Cold
• RTECS: NM2430000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 97%; 98%; 98+%
• Empirical Formula (Hill Notation): C8H7NO

DETAILS

MP Biomedicals - 02100748

Crystalline

Sigma Aldrich - H31859

Packaging
1 g in glass bottle
Application

• Reactant for preparation of (oxoimidazolidinyl/oxopyrimidinyl)benzenesulfonates as antitumor agents and tubulin inhibitors1
• Reactant for preparation of anthranilic acids2
• Reactant for preparation of indole compounds as dopamine D2 receptor antagonists3
• Reactant for preparation of naphthalimide- or carbazole-containing human β-adrenoceptor ligands4
• Reactant for preparation of melanins as nature-inspired radioprotectors5
• Reactant for preparation of 5-vinyl-3-pyridinecarbonitriles as PKCθ inhibitors6

Toronto Research Chemicals - H943510

5-Hydroxyindole is a hydroxylated indole used as a building block in the preparation of various pharmaceutical compounds such as indole based neurochemicals. 5-Hydroxyindole is a metabolite of Tryptophan (T894800). 5-Hydroxyindole displayed weak inhibitor

REFERENCES

• Yamazaki, Y. et al.: Zeitsch. Naturforsch. C: J. Biosci., 65, 49 (2010)
• Kay, W.W. et al.: Gen. Pharmacol., 8, 201 (2010)
• Ghebregzabher, M. et al.: J. Chrom. Biomed. Appl., 222, 191 (2010)