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395307

Sigma-Aldrich

Methyl indole-3-carboxylate

99%

Synonym(s):
3-Carbomethoxyindole, 3-Methoxycarbonylindole, Methyl indolyl-3-carboxylate
Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
Molecular Weight:
175.18
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

powder

mp

149-152 °C (lit.)

SMILES string

COC(=O)c1c[nH]c2ccccc12

InChI

1S/C10H9NO2/c1-13-10(12)8-6-11-9-5-3-2-4-7(8)9/h2-6,11H,1H3

InChI key

QXAUTQFAWKKNLM-UHFFFAOYSA-N

General description

Methyl indole-3-carboxylate (3-Methoxycarbonylindole, 3-Carbomethoxyindole, Methyl indolyl-3-carboxylate) has been extracted from the marine Streptomyces sp. 060524. Its crystal structure indicates the presence of inter­molecular N-H…O hydrogen bond. It is also obtained during the isolation of sorazinones A and B from Sorangium cellulosum strain Soce895. It undergoes regioselective dibromination with bromine in acetic acid to afford methyl 5,6-dibromoindole-3-carboxylate.

Application

Reactant for preparation of:
  • Nitric oxide synthase (nNOS) inhibitorS
  • Protein kinase c alpha (PKCα) inhibitors
  • Inhibitors of the C-terminal domain of RNA polymerase II as antitumor agents
  • Kinase insert domain receptor (KDR) inhibitors
  • Organocatalysts for the anti-Mannich reaction
  • Very late antigen-4 (VLA-4) antagonists
  • Inhibitors of Human 5-Lipoxygenase
  • Serotonin 5-HT4 receptor antagonists
  • Hyaluronidase inhibitors

Reactant for:
  • Enantioselective Meerwein-Eschenmoser Claisen rearrangement reactions†

Packaging

25 g in glass bottle

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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