methyl 4-methoxy-1H-indole-2-carboxylate

• ChemBase ID: 77081
• Molecular Formular: C11H11NO3
• Molecular Mass: 205.20994
• Monoisotopic Mass: 205.07389322
• SMILES: [nH]1c2c(c(ccc2)OC)cc1C(=O)OC
• Canonical SMILES: COC(=O)c1[nH]c2c(c1)c(OC)ccc2
• InChI: InChI=1S/C11H11NO3/c1-14-10-5-3-4-8-7(10)6-9(12-8)11(13)15-2/h3-6,12H,1-2H3
• InChIKey: GLCZQTLCVLVFGV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 4-methoxy-1H-indole-2-carboxylate
• IUPAC Traditional name: methyl 4-methoxy-1H-indole-2-carboxylate
• Synonyms: Methyl 4-methoxy-2-indolecarboxylate; Methyl 4-methoxy-1H-indole-2-carboxylate; 4-Methoxyindole-2-carboxylic acid methyl ester; Methyl 4-methoxyindole-2-carboxylate; 4-甲氧基-2-吲哚羧酸甲酯; 4-甲氧吲哚-2-羧酸甲酯

Database IDs

• CAS Number: 111258-23-2
• MDL Number: MFCD00134300
• PubChem SID: 162041955; 24862538
• PubChem CID: 688172

CALCULATED PROPERTIES

• Acid pKa: 11.480188
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.8378142
• LogD (pH = 7.4): 1.837783
• Log P: 1.8378147
• Molar Refractivity: 55.5105 cm^3
• Polarizability: 22.478361 Å^3
• Polar Surface Area: 51.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 140-142 °C(lit.); 140-142°C; 140-142°C°C

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 否

Product Information

• Purity: 99%
• Empirical Formula (Hill Notation): C11H11NO3

DETAILS

Sigma Aldrich - 365564

Packaging
1 g in glass bottle
250 mg in glass bottle
Application

• reactant in [3+2] annulation reactions1
• reactant in preparation of inhibitors of mammalian secreted phospholipases A22
• reactant in Heck reactions3
• reactant in preparation of indole fatty alcohol derivatives4
• reactant in methylation reactions5