ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate

• ChemBase ID: 60175
• Molecular Formular: C12H13NO3
• Molecular Mass: 219.23652
• Monoisotopic Mass: 219.08954328
• SMILES: c1(c(c2c([nH]1)ccc(c2)O)C(=O)OCC)C
• Canonical SMILES: Cc1c(C(=O)OCC)c2c([nH]1)ccc(c2)O
• InChI: InChI=1S/C12H13NO3/c1-3-16-12(15)11-7(2)13-10-5-4-8(14)6-9(10)11/h4-6,13-14H,3H2,1-2H3
• InChIKey: BSNHKSUAAMJXBB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate
• IUPAC Traditional name: ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate
• Synonyms: NSC 405600; Ethyl 5-hydroxy-2-methylindole-3-carboxylate; Ethyl 5-hydroxy-2-methyl-1H-indole-3-carboxylate; ETHYL 5-HYDROXY-2-METHYLINDOLE-3-CARBOXYLATE; 5-羟基-2-甲基吲哚-3-羧酸乙酯

Database IDs

• CAS Number: 7598-91-6
• EC Number: 231-507-7
• MDL Number: MFCD00044575
• PubChem SID: 162025916; 24894500
• PubChem CID: 82073

CALCULATED PROPERTIES

• Acid pKa: 9.494522
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.328245
• LogD (pH = 7.4): 2.3248312
• Log P: 2.3282888
• Molar Refractivity: 61.049 cm^3
• Polarizability: 24.164963 Å^3
• Polar Surface Area: 62.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 200 - 202°C; 205-208 °C(lit.)
• Hydrophobicity(logP): 2.992

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 97%
• Empirical Formula (Hill Notation): C12H13NO3

DETAILS

MP Biomedicals - 05205207

MP Biomedicals Rare Chemical collection

Sigma Aldrich - E31804

Packaging
1 g in glass bottle
Application
Reactant for preparation of:
• Potential anti-inflammatory and analgesic agents1
• Histamine-3 receptor inverse agonists for the treatment of obesity2
• Tubulin Polymerization Inhibitors3
• 4,7-dioxoindole-3-methyl prodrugs4
• Antagonists at M4 muscarinic receptors5