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C92006 Sigma-Aldrich

Indole-5-carbonitrile

99%

Synonym: 5-Cyanoindole

  • CAS Number 15861-24-2

  • Empirical Formula (Hill Notation) C9H6N2

  • Molecular Weight 142.16

  •  Beilstein/REAXYS Number 116738

  •  EC Number 239-986-4

  •  MDL number MFCD00005669

  •  PubChem Substance ID 24893140

  •  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   99%
mp   106-108 °C (lit.)
SMILES string   N#Cc1ccc2[nH]ccc2c1
InChI   1S/C9H6N2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-5,11H
InChI key   YHYLDEVWYOFIJK-UHFFFAOYSA-N

Description

Application

• Reactant for parallel synthesis of dihydroisoquinolines via silver and L-proline co-catalyzed three-component coupling reaction
• Reactant for chemoselective and regioselective preparation of benzoyl indoles
• Reactant for preparation of novel PPARα/γ dual agonists for potential treatment of metabolic syndrome and IDDM
• Reactant for preparation of 4,5-dihydrocyclopenta[c]quinolines by palladium-catalyzed ring-expansion reaction alkynes, using O2 as the oxidant
• Reactant for preparation of vinylindoles by hydroarylation of alkynes using indium bromide catalyst
• Reactant for gold catalyzed direct alkynylation using a benziodoxolone based hypervalent iodine reagent

Packaging

5, 10 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
NL5993120
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

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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

Related Content

Indoles, Purines, and Their Isosteres

Substituted indoles and purines have frequently been referred to as “privileged structures” since they are capable of binding to multiple receptors with high affinity, and thus have applications acro...
Keywords: Building blocks, Medicinal chemistry

Peer-Reviewed Papers
15

References

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