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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:
1477-50-5
Molecular Weight:
161.16
Beilstein:
124132
EC Number:
216-030-4
MDL number:
MFCD00005611
UNSPSC Code:
12352100
PubChem Substance ID:
24895981
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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Related Categories

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

Certificates of Analysis (COA)

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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
R Rama Suresh et al.
The Journal of organic chemistry, 77(16), 6959-6969 (2012-07-26)
Two methodologies, one involving Ar-I reactivity and the other through C-H functionalization, for the formation of indolo[2,3-c]pyrane-1-ones via the corresponding allenes, are presented. A highly efficient approach to indolo[2,3-c]pyrane-1-one derivatives through the Pd-catalyzed regioselective annulation of allenes with 3-iodo-1-alkylindole-2-carboxylic acids
Hideyuki Shiozawa et al.
Journal of the American Chemical Society, 124(15), 3914-3919 (2002-04-11)
Glycopeptide antibiotics of the vancomycin group bind to bacterial cell wall analogue precursors, and typically also form dimers. We have studied the interplay between these two sets of noncovalent bonds formed at separate interfaces. Indole-2-carboxylic acid (L) forms a set
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