Skip to Content
MilliporeSigma
All Photos(1)

Documents

511188

Sigma-Aldrich

Methyl indole-5-carboxylate

99%

Synonym(s):

Indole-5-carboxylic acid, methyl ester

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
1011-65-0
Molecular Weight:
175.18
MDL number:
MFCD00153023
UNSPSC Code:
12352100
PubChem Substance ID:
24873426
NACRES:
NA.22

Quality Level

100

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Fei Yang et al.
Organic letters, 12(22), 5214-5217 (2010-10-23)
A novel cross dehydrogenative coupling (CDC) reaction of N,N-dimethylanilines with methyl ketones by cooperative copper and aminocatalysis has been developed, which leads to the formation of β-arylamino ketones in 42-73% yields. Moreover, the copper-catalyzed alkylation of free (NH) indoles with
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)
Liu, Z.; et al.
Letters in Organic Chemistry, 7, 666-666 (2010)
Wen-Jie Lu et al.
European journal of medicinal chemistry, 64, 498-511 (2013-05-21)
This report describes the synthesis, and in vitro and in vivo antimalarial evaluations of certain ester-modified neocryptolepine (5-methyl-5H-indolo[2,3-b]quinoline) derivatives. The modifications were carried out by introducing ester groups at the C2 and/or C9 position on the neocryptolepine core and the
Wang, T. C.; et al.
Chinese Chemical Letters = Zhongguo Hua Xue Kuai Bao, 21, 1407-1407 (2010)
View All Related Papers

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