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Key Documents

I5109

Sigma-Aldrich

Indole-2-carboxylic acid

98%

Synonym(s):

2-Carboxyindole, 2-Indolylformic acid, NSC 16598

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About This Item

Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
Molecular Weight:
161.16
Beilstein:
124132
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

mp

202-206 °C (lit.)

SMILES string

OC(=O)c1cc2ccccc2[nH]1

InChI

1S/C9H7NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-5,10H,(H,11,12)

InChI key

HCUARRIEZVDMPT-UHFFFAOYSA-N

Gene Information

human ... SRD5A1(6715)
rat ... Grin2a(24409)

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Application

  • Reactant for total synthesis of (±)-dibromophakellin and analogs
  • Reactant for synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine
  • Reactant for stereoselective preparation of renieramycin G analogs
  • Reactant for preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization
  • Reactant for Pd-catalyzed cyclization
  • Reactant for preparation of N,N′-(pentane)diylbis[indolecarboxamide] and N,N′-[phenylenebis(methylene)]bis[indolecarboxamide] derivatives

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

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R Di Fabio et al.
Journal of medicinal chemistry, 40(6), 841-850 (1997-03-14)
A series of indole-2-carboxylates bearing suitable chains at the C-3 position of the indole nucleus was synthesized and evaluated in terms of in vitro affinity using [3H]glycine binding assay and in vivo potency by inhibition of convulsions induced by N-methyl-D-aspartate
Stephen P Nighswander-Rempel et al.
Photochemistry and photobiology, 84(3), 613-619 (2008-01-23)
We have synthesized a compound ideally suited to the study of structure-function relationships in eumelanin synthesis. N-methyl-5-hydroxy-6-methoxy-indole (MHMI) has key functional groups strategically placed on the indole framework to hinder binding in the 2, 5, 6 and 7 positions. Thus
C Kuehm-Caubere et al.
Journal of medicinal chemistry, 40(8), 1201-1210 (1997-04-11)
Series of indole-2-carboxamide and cycloalkeno[1,2-b]indole derivatives were synthesized and evaluated in order to determine the necessary structural requirements for a high inhibition of human LDL copper-induced peroxidation. Various modulations were systematically performed on the indole and cycloalkeno[1,2-b]indole nuclei as well
Marine Valette et al.
Physiology and molecular biology of plants : an international journal of functional plant biology, 26(12), 2537-2551 (2021-01-12)
Rhizosphere bacteria, whether phytopathogenic or phytobeneficial, are thought to be perceived by the plant as a threat. Plant Growth-Promoting Rhizobacteria (PGPR), such as many strains of the Azospirillum genus known as the main phytostimulator of cereals, cooperate with host plants
James F Dropinski et al.
Bioorganic & medicinal chemistry letters, 15(22), 5035-5038 (2005-09-13)
A series of novel aryl indole-2-carboxylic acids has been identified as potent selective PPARgamma modulators. Their chemical synthesis and in vitro activities are discussed. Compound 5 was selected for in vivo testing in the db/db mouse model of type 2

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