465321

1-Methyl-3-indoleacetic acid

98%

• Synonym(s): 2-(N-Methylindole-3-yl)acetic acid, NSC 78007
• Empirical Formula (Hill Notation): C₁₁H₁₁NO₂
• CAS Number: 1912-48-7
• Molecular Weight: 189.21
• MDL number: MFCD00130160
• UNSPSC Code: 12352100
• PubChem Substance ID: 24870268
• NACRES: NA.22

Properties

• assay: 98%
• mp: 126-128 °C (lit.)
• SMILES string: Cn1cc(CC(O)=O)c2ccccc12
• 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)
• InChI key: NAIPEFIYIQFVFC-UHFFFAOYSA-N

Description

General description

1-Methyl-3-indoleacetic acid is an indole derivative. Direct and riboflavin- or Rose-Bengal-sensitized photo-oxidation of 1-methyl-3-indoleacetic acid in aqueous buffer (pH 5 or pH 8) containing 10% methanol has been studied.[1]

Application

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

Safety Information

• pictograms: GHS05,GHS07
• signalword: Danger
• hcodes: H302,H315,H318,H335
• pcodes: P261 - P264 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable