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I5109 Sigma-Aldrich

Indole-2-carboxylic acid

98%

Synonym: 2-Carboxyindole, 2-Indolylformic acid, NSC 16598

  • CAS Number 1477-50-5

  • Empirical Formula (Hill Notation) C9H7NO2

  • Molecular Weight 161.16

  •  Beilstein/REAXYS Number 124132

  •  EC Number 216-030-4

  •  MDL number MFCD00005611

  •  PubChem Substance ID 24895981

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
Quality Level   100
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)

Description

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

Packaging

5, 10, 50 g in poly bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Indoles

Sigma-Aldrich is proud to offer a new series of ChemFiles—called Privileged Structures, to our Drug Discovery and Organic Synthesis customers. Each piece will highlight a specific motif, selected app...
Chemfiles Volume 4 Article 8
Keywords: Building blocks, Cardiovascular, Diabetes, Diseases, Drug discovery, Medicinal chemistry, Organic synthesis, Respiratory

Peer-Reviewed Papers
15

References

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