465321
1-Methyl-3-indoleacetic acid
98%
Synonym(s):
2-(N-Methylindole-3-yl)acetic acid, NSC 78007
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About This Item
Empirical Formula (Hill Notation):
C11H11NO2
CAS Number:
Molecular Weight:
189.21
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
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)
SMILES string
Cn1cc(CC(O)=O)c2ccccc12
InChI key
NAIPEFIYIQFVFC-UHFFFAOYSA-N
assay
98%
mp
126-128 °C (lit.)
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.
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
signalword
Danger
hcodes
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Direct and dye-sensitized aqueous photo-oxidation of 3-indoleacetic acid, methyl-3-indoleacetate and 1-methyl-3-indoleacetic acid I: Analysis of products.
Amat-Guerri F, et al.
Journal of Photochemistry and Photobiology A: Chemistry, 50(3), 361-375 (1990)
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