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I5400

Sigma-Aldrich

Indole-5-carboxylic acid

99%

Synonym(s):
5-Carboxyindole
Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
Molecular Weight:
161.16
Beilstein:
124391
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

mp

211-213 °C (lit.)

SMILES string

OC(=O)c1ccc2[nH]ccc2c1

InChI

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

InChI key

IENZCGNHSIMFJE-UHFFFAOYSA-N

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General description

Indole-5-carboxylic acid is an indole derivative. On electropolymerization, it affords electroactive polymer film of poly(indole-5-carboxylic-acid). Different concentrations of indole-5-carboxylic acid in sulfuric acid solution has been investigated for the preventive action against mild steel corrosion. On electropolymerization it affords a trimeric product. Characterization studies of the trimeric product by 1H NMR and various one- and two-dimensional NMR techniques have been reported.

Application

Indole-5-carboxylic acid is the suitable reagent used to study the intramolecular excited state proton transfer in indole-2-carboxylic acid and indole-5-carboxylic acid in various solvents in acidic, basic, and neutral media by steady state and time resolved fluorescence spectroscopy. It may be used in the electrochemical synthesis of poly(indole-5-carboxylic acid) (PICA) films.
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Packaging

1, 5 g in poly bottle

Storage Class Code

13 - Non 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

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Characterization of the unsymmetrical trimer of indole-5-carboxylic acid by proton NMR spectroscopy.
Mackintosh JG, et al.
Magnetic Resonance in Chemistry, 32(9), 559-561 (1994)
Electropolymerisation of indole-5-carboxylic acid.
GordonaMackintosh J and Andrew R.
J. Chem. Soc., Faraday, 90(8), 1121-1125 (1994)
Inhibitive action of indole-5-carboxylic acid towards corrosion of mild steel in deaerated 0.5 M sulfuric acid solutions.
Quartarone G, et al.
Applied Surface Science, 252(23), 8251-8257 (2006)
Electrodeposition of poly (indole-5-carboxylic acid) in boron trifluoride diethyl etherate containing additional diethyl ether.
Nie G, et al.
Electrochimica Acta, 52(24), 7097-7106 (2007)
Excited state proton transfer in indole-2-carboxylic acid and indole-5-carboxylic acid.
Bangal PR and Chakravorti S.
The Journal of Physical Chemistry A, 103(43), 8585-8594 (1999)

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