525022

4-Aminoindol

97%

• Synonym(e): 4-Indolamin
• Empirische Formel (Hill-System): C₈H₈N₂
• CAS-Nummer: 5192-23-4
• Molekulargewicht: 132.16
• Beilstein: 114919
• MDL-Nummer: MFCD01076559
• UNSPSC-Code: 12352100
• PubChem Substanz-ID: 24874461
• NACRES: NA.22

Eigenschaften

• Assay: 97%
• mp (Schmelzpunkt): 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
• InChIKey: LUNUNJFSHKSXGQ-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H315,H319,H335
• P-Sätze: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Gefahreneinstufungen: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Zielorgane: Respiratory system
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves