I3750

3-Indoleacetic acid

98%

• Synonym(s): Heteroauxin, IAA
• Empirical Formula (Hill Notation): C₁₀H₉NO₂
• CAS Number: 87-51-4
• Molecular Weight: 175.18
• Beilstein/REAXYS Number: 143358
• EC Number: 201-748-2
• MDL number: MFCD00005636
• UNSPSC Code: 12352100
• PubChem Substance ID: 24896043
• NACRES: NA.22

Properties

• assay: 98%
• mp: 165-169 °C (lit.)
• SMILES string: OC(=O)Cc1c[nH]c2ccccc12
• InChI: 1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
• InChI key: SEOVTRFCIGRIMH-UHFFFAOYSA-N

Description

General description

3-Indoleacetic acid (IAA) is a naturally occurring hydrophilic organic compound consists of an unsaturated aromatic ring that is commonly used in the synthesis of indolylated diarylmethanes, α-acetoxyl ketones, and Indolmethyl-Chromones via copper catalyzed coupling reactions.

Application

3-Indoleacetic acid (IAA) can be used as a building block to synthesize ,(±) harmacine using 4,4-diethoxybutan-1-amine via an acid-catalyzed acyl iminium ion cyclization reaction.
(±)-Harmacine is a vital step in the synthesis of a variety of indole alkaloids and dopamine/serotonin receptor ligands. IAA can also be used in the preparation of alkaloid (±)-19-hydroxyibogamine.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)