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632422 Sigma-Aldrich

Indole-4-carboxaldehyde

97%

Synonym: 4-Formylindole, NSC 337264

  • CAS Number 1074-86-8

  • Empirical Formula (Hill Notation) C9H7NO

  • Molecular Weight 145.16

  •  MDL number MFCD01632221

  •  PubChem Substance ID 24882325

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Properties

Related Categories Aldehydes, Building Blocks, C7 to C9, C9, Carbonyl Compounds,
assay   97%
mp   139-143 °C (lit.)
SMILES string   O=Cc1cccc2[nH]ccc12
InChI   1S/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H
InChI key   JFDDFGLNZWNJTK-UHFFFAOYSA-N

Description

General description

Indole-4-carboxaldehyde participates in the synthesis of arcyriacyanin A. Synthesis of 4-indole-4-carboxaldehyde has been reported. Intramolecular Friedel-Crafts (FC) acylation of indole-4-carboxaldehyde has been reported.

Application

• reactant in Biginelli reaction
• reactant in synthesis of aurora kinase A inhibitors
• reactant in preparation of antitumor agents
• reactant in intramolecular Friedel-Crafts acylation
• reactant in preparation of inhibitors of cell division in E. coli
• reactant in synthesis of Hantzsch pyridine-containing Schiff bases

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Friedel–Crafts Acylation

The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form m...
Keywords: Acylations, Catalysis, Electrophilic aromatic substitution, Microwave synthesis, Substitutions

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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