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465321

Sigma-Aldrich

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
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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

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

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

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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