2-(1-methyl-1H-indol-3-yl)acetic acid

• ChemBase ID: 42099
• Molecular Formular: C11H11NO2
• Molecular Mass: 189.21054
• Monoisotopic Mass: 189.0789786
• SMILES: c1(cn(c2c1cccc2)C)CC(=O)O
• Canonical SMILES: OC(=O)Cc1cn(c2c1cccc2)C
• InChI: InChI=1S/C11H11NO2/c1-12-7-8(6-11(13)14)9-4-2-3-5-10(9)12/h2-5,7H,6H2,1H3,(H,13,14)
• InChIKey: NAIPEFIYIQFVFC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1-methyl-1H-indol-3-yl)acetic acid
• IUPAC Traditional name: (1-methylindol-3-yl)acetic acid
• Synonyms: 2-(1-Methyl-1H-indol-3-yl)acetic acid; 2-(N-Methylindole-3-yl)acetic acid; NSC 78007; 1-Methyl-3-indoleacetic acid; (1-methyl-1{H}-indol-3-yl)acetic acid; 1-甲基-3-吲哚乙酸

Database IDs

• CAS Number: 1912-48-7
• MDL Number: MFCD00130160
• PubChem SID: 162046862; 24870268
• PubChem CID: 254166

CALCULATED PROPERTIES

• Acid pKa: 4.7133045
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0817847
• LogD (pH = 7.4): -0.69587266
• Log P: 1.9334322
• Molar Refractivity: 53.3488 cm^3
• Polarizability: 21.484638 Å^3
• Polar Surface Area: 42.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 126 - 128°C; 126-128 °C(lit.); 133 - 135 °C; 133-135°C
• Partition Coefficient: 2.427
• Hydrophobicity(logP): 1.87

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-37/38-41
• Safety Statements: 26-39
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338

Product Information

• Purity: >95%; 95%; 95+%; 98%
• Empirical Formula (Hill Notation): C11H11NO2

DETAILS

Sigma Aldrich - 465321

Packaging
5 g in glass bottle
Application

• Reactant for enantioselective preparation of α-aryl alkylcarboxylic acids1
• Reactant for preparation of PKC inhibitor methylindolylpyridinylmethylpiperidinylindolylpyrroledione for protein kinase C imaging2
• Reactant for stereoselective preparation of δ-lactones via Michael addition/lactonization with unsaturated carboxylates3
• Reactant for stereoselective preparation of vindorosine, vindoline, and analogs4
• Reactant for preparation of (indolyl)pyrrol-2-ones as VEGF-R inhibitors, antiangiogenic agents, and protein kinase inhibitors5
• Reactant for synthesis of 3-aryl-5-alkyl-2,5-dihydrofuran-2-ones and their carbanalogues as antifungal agents6