ethyl 1H-indole-3-carboxylate

• ChemBase ID: 141482
• Molecular Formular: C11H11NO2
• Molecular Mass: 189.21054
• Monoisotopic Mass: 189.0789786
• SMILES: CCOC(=O)c1c[nH]c2c1cccc2
• Canonical SMILES: CCOC(=O)c1c[nH]c2c1cccc2
• InChI: InChI=1S/C11H11NO2/c1-2-14-11(13)9-7-12-10-6-4-3-5-8(9)10/h3-7,12H,2H2,1H3
• InChIKey: XOUHVMVYFOXTMN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1H-indole-3-carboxylate
• IUPAC Traditional name: ethyl 1H-indole-3-carboxylate
• Synonyms: 3-(Ethoxycarbonyl)indole; Indole-3-carboxylic acid ethyl ester; NSC 63796; Ethyl indole-3-carboxylate; Ethyl 1H-indole-3-carboxylate; 吲哚-3-羧酸乙酯

Database IDs

• CAS Number: 776-41-0
• MDL Number: MFCD00228454
• PubChem SID: 24885636; 162235716
• PubChem CID: 247965

CALCULATED PROPERTIES

• Acid pKa: 12.191266
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.4322927
• LogD (pH = 7.4): 2.432286
• Log P: 2.4322927
• Molar Refractivity: 53.9184 cm^3
• Polarizability: 21.814083 Å^3
• Polar Surface Area: 42.09 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 120-124 °C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 96%; 97%
• Empirical Formula (Hill Notation): C11H11NO2

DETAILS

Sigma Aldrich - 681466

Application
Precursor to 1,2-aziridinopyrrolo-indoles.5
Reactant for preparation of:
• Indole-based heterocycles for synthesis of indole-based p38 inhibitors and gramines1
• Glycine receptor ligands2
• Inhibitors of Human 5-Lipoxygenase3
• Antimicrobial agents4
Packaging
1, 5 g in glass bottle