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Sigma-Aldrich

Methyl indole-3-carboxylate

99%

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Synonym(s):
3-Carbomethoxyindole, 3-Methoxycarbonylindole, Methyl indolyl-3-carboxylate
Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
942-24-5
Molecular Weight:
175.18
MDL number:
MFCD00189407
PubChem Substance ID:
24864651
NACRES:
NA.22

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

Related Categories

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†

Storage Class Code

11 - 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

Regulatory Information

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Thomas B Parsons et al.
Organic & biomolecular chemistry, 9(14), 5021-5023 (2011-06-07)
Treatment of methyl indole-3-carboxylate with bromine in acetic acid gives methyl 5,6-dibromoindole-3-carboxylate regioselectively, from which the parent 5,6-dibromoindole can be accessed via a one-pot, microwave-mediated ester hydrolysis and decarboxylation. Application of these building blocks in syntheses of natural and non-natural
Rolf Jansen et al.
Journal of natural products, 77(11), 2545-2552 (2014-11-15)
Nannozinones A (1) and B (2) were discovered as metabolites of the recently isolated Nannocystis pusilla strain MNa10913 belonging to the poorly studied myxobacterial family Nannocystaceae. In contrast, the structurally related sorazinones A (5) and B (6) were isolated from
Methyl indole-3-carboxylate.
Hu SC, et al.
Acta Crystallographica Section E, Structure Reports Online, 61(6), o1654-o1656 (2005)
Azadeh Esfandiari et al.
Plant physiology and biochemistry : PPB, 115, 343-353 (2017-04-19)
Broccoli (Brassica oleracea L. var. italica) sprouts contain glucosinolates (GLs) that when hydrolysed yield health promoting isothiocyanates such as sulforaphane (SF). SF content can be increased by salt (NaCl) stress, although high salt concentrations negatively impact plant growth. Salicylic acid

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