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511188

Sigma-Aldrich

Methyl indole-5-carboxylate

99%

Synonym(s):
Indole-5-carboxylic acid, methyl ester
Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
Molecular Weight:
175.18
MDL number:
PubChem Substance ID:

Quality Level

assay

99%

mp

126-128 °C (lit.)

SMILES string

COC(=O)c1ccc2[nH]ccc2c1

InChI

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

InChI key

DRYBMFJLYYEOBZ-UHFFFAOYSA-N

General description

Methyl indole-5-carboxylate (Methyl 1H-indole-5-carboxylate), a substituted 1H-indole, can be prepared by the esterification of indole-5-carboxylic acid. Its efficacy as a substrate for indigoid generation has been assessed.

Application

Methyl indole-5-carboxylate may be used as a reactant in the following processes:
  • biosynthesis of inhibitors of protein kinases
  • metal-free Friedel-Crafts alkylation
  • preparation of diphenylsulfonium ylides from Martin′s sulfurane
  • cross dehydrogenative coupling reactions
  • synthesis of indirubin derivatives
  • preparation of aminoindolylacetates
Methyl indole-5-carboxylate may be used in the preparation of:
  • methyl indoline-5-carboxylate
  • 1H-indole-5-carbohydrazide
  • dimethyl 1H-indole-3,5-dicarboxylate

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - 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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

A facial synthesis and antimicrobial activity of some pyrazole derivatives carrying indole.
Sarma KN, et al.
Journal of Chemistry, 7(3), 745-750 (2010)
Liu, Z.; et al.
Letters in Organic Chemistry, 7, 666-666 (2010)
Wang, T. C.; et al.
Chinese Chemical Letters = Zhongguo Hua Xue Kuai Bao, 21, 1407-1407 (2010)
Ube, H.; et al.
Tetrahedron Asymmetry, 21, 1203-1203 (2010)
A direct ylide transfer to carbonyl derivatives and heteroaromatic compounds.
Xueliang Huang et al.
Angewandte Chemie (International ed. in English), 49(47), 8979-8983 (2010-10-13)

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