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N17602 Sigma-Aldrich

5-Nitroindole

98%

Synonym: NSC 520594

  • CAS Number 6146-52-7

  • Empirical Formula (Hill Notation) C8H6N2O2

  • Molecular Weight 162.15

  •  Beilstein/REAXYS Number 383777

  •  EC Number 228-153-0

  •  MDL number MFCD00005673

  •  PubChem Substance ID 24897523

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Heterocyclic Building Blocks, Indoles,
Quality Level   100
assay   98%
mp   140-142 °C (lit.)
storage temp.   room temp
SMILES string   [O-][N+](=O)c1ccc2[nH]ccc2c1
InChI   1S/C8H6N2O2/c11-10(12)7-1-2-8-6(5-7)3-4-9-8/h1-5,9H
InChI key   OZFPSOBLQZPIAV-UHFFFAOYSA-N

Description

Application

Reactant for preparation of:
• Pharmaceutically active 2-oxo-1-pyrrolidine analogues
• Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
• Protein Kinase Inhibitors and antiproliferative agents
• Positive Allosteric Modulators of Metabotropic Glutamate Receptor 4 (mGlu4)
• Antifungal agents
• Cannabinoid receptor type 1 (CB1) antagonists
• Potential anticancer agents
• Potential antivascular agents
• Selective Anti-leukemic agents
• Anti human immunodeficiency virus subtype 1 (HIV-1) agents

Packaging

25 g in poly bottle

5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
NM1168200
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
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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