methyl 6-methoxy-1H-indole-2-carboxylate

• ChemBase ID: 54203
• Molecular Formular: C11H11NO3
• Molecular Mass: 205.20994
• Monoisotopic Mass: 205.07389322
• SMILES: c1c(cc2c(c1)cc([nH]2)C(=O)OC)OC
• Canonical SMILES: COc1ccc2c(c1)[nH]c(c2)C(=O)OC
• InChI: InChI=1S/C11H11NO3/c1-14-8-4-3-7-5-10(11(13)15-2)12-9(7)6-8/h3-6,12H,1-2H3
• InChIKey: OPUUCOLVBDQWEY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 6-methoxy-1H-indole-2-carboxylate
• IUPAC Traditional name: methyl 6-methoxy-1H-indole-2-carboxylate
• Synonyms: 6-Methoxy-1H-indole-2-carboxylic acid methyl ester; 2-Methoxycarbonyl-6-methoxyindole; 6-Methoxyindole-2-carboxylic acid methyl ester; Methyl 6-methoxy-2-indolecarboxylate; methyl 6-methoxy-1H-indole-2-carboxylate; 6-甲氧基-2-吲哚羧酸甲酯

Database IDs

• CAS Number: 98081-83-5
• MDL Number: MFCD00134301
• PubChem SID: 162058966; 24862540
• PubChem CID: 688173

CALCULATED PROPERTIES

• Acid pKa: 11.204147
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.8378139
• LogD (pH = 7.4): 1.8377548
• Log P: 1.8378147
• Molar Refractivity: 55.5105 cm^3
• Polarizability: 22.474142 Å^3
• Polar Surface Area: 51.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 117-119 °C(lit.)
• Partition Coefficient: 2.207

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false

Product Information

• Purity: 95+%; 98%; 99%
• Empirical Formula (Hill Notation): C11H11NO3

DETAILS

Sigma Aldrich - 365572

Packaging
1 g in glass bottle
Application
Reactant for preparation of:
• Benzoxazole containing indole analogs as peroxisome proliferator-activated receptor-γ/δ dual agonists1
• Potent antiproliferative agent against human leukemia K562 cells2
• Indole-indolone scaffold via [3+2] annulation of arynes3
• Latonduine derivatives via intramolecular Heck reaction as possible anticancer agents4
• Arylthioindoles as potent inhibitors of tubulin polymerization5
• Heterocycle-fused derivatives of 1-oxo-1,2,3,4-tetrahydropyrazine via Ugi condensation6
• Indole fatty alcohols (IFAs) as promoters of differentiation of neural stem cell derived neurospheres into neurons. Potential application for treatment of neurodegenerative diseases7
• Light-dependent tumor necrosis factor-α antagonists8
• 2-substituted indole melatonin receptor ligands9