395307

Sigma-Aldrich

Methyl indole-3-carboxylate

99%

Synonym(s):
Methyl indolyl-3-carboxylate, 3-Carbomethoxyindole, 3-Methoxycarbonylindole
Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
Molecular Weight:
175.18
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

99%

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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
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...
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...

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.