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525022 Sigma-Aldrich

4-Aminoindole

97%

Synonym: (Indol-4-yl)amine, 4-Indolamine

  • CAS Number 5192-23-4

  • Empirical Formula (Hill Notation) C8H8N2

  • Molecular Weight 132.16

  •  Beilstein/REAXYS Number 114919

  •  MDL number MFCD01076559

  •  PubChem Substance ID 24874461

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
assay   97%
mp   106-109 °C (lit.)
SMILES string   Nc1cccc2[nH]ccc12
InChI   1S/C8H8N2/c9-7-2-1-3-8-6(7)4-5-10-8/h1-5,10H,9H2
InChI key   LUNUNJFSHKSXGQ-UHFFFAOYSA-N

Description

General description

4-Aminoindole is an indole derivative. Its cytokinin activity has been assessed by tobacco pith callus bioassay. 4-Aminoindole can be prepared by reacting 2,6-dinitrotoluene and N,N-dimethylformamide dimethylacetal in anhydrous DMF.

Application

4-Aminoindole may be used to synthesize:
• macrolactam tumour promoter indolactam V
• tricyclic structure of 2-substituted-pyrrolo[2,3-h]quinolin-4-one
• 4-azidoindole

Reactant for preparation of:
• Inhibitors of bacterial thymidylate synthase
• Mimetics of non-alkaloid toxin lignan anticancer and antiviral agent Podophyllotoxin (PPT)
• Inhibitors of Gli1-mediated transcription in the Hedgehog pathway
• Protein kinase C θ (PKCθ) inhibitors
• Indolic non-peptidic HIV protease inhibitors
• Transient receptor potential cation channel subfamily V member 1 (TRPV1) antagonists
• Cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors
• 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1) inhibitors
• Short chain 4-substituted indoles as potent αvβ3 antagonist
• Ligands of serotonin transporter and 5-HT1A receptors

Packaging

500 mg in amber glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning-Warning
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

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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