81881-74-5

Basic information

• Product Name: C-(1H-INDOL-5-YL)-METHYLAMINE
• Synonyms: 5-(aminomethyl)-indol;INDOLE-5-METHYLAMINE;C-(1H-INDOL-5-YL)-METHYLAMINE;(1H-INDOL-5-YL)METHANAMINE;5-(AMINOMETHYL)INDOLE;(1H-Indol-5-yl)methylamine;1H-Indole-5-MethanaMine;Indole-5-methanamine
• CAS NO: 81881-74-5
• Molecular Formula: C₉H₁₀N₂
• Molecular Weight: 146.19
• Product Categories: pharmacetical;Building Blocks;Heterocyclic Building Blocks;Indoles;Building Blocks;C7 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Amines;Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 81881-74-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 114-118 °C
• Boiling Point: 335.6 °C at 760 mmHg
• Flash Point: 183.3 °C
• Appearance: /
• Density: 1.199 g/cm³
• Vapor Pressure: 0.000118mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 17.07±0.30(Predicted)
• CAS DataBase Reference: C-(1H-INDOL-5-YL)-METHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: C-(1H-INDOL-5-YL)-METHYLAMINE(81881-74-5)
• EPA Substance Registry System: C-(1H-INDOL-5-YL)-METHYLAMINE(81881-74-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: NL4461500
• Hazardous Substances Data: 81881-74-5(Hazardous Substances Data)

Usage

Description

C-(1H-INDOL-5-YL)-METHYLAMINE, also known as 5-(aminomethyl)indole, is an organic compound that serves as a versatile building block in the synthesis of various pharmaceutical agents and bioactive molecules. It is characterized by the presence of an indole ring and an aminomethyl group, which contribute to its reactivity and potential applications in medicinal chemistry.

Uses

Used in Pharmaceutical Synthesis:
C-(1H-INDOL-5-YL)-METHYLAMINE is used as a reactant for the preparation of various pharmaceutical agents, including HIV-1 integrase inhibitors, inhibitors of Gli1-mediated transcription in the Hedgehog pathway, SCIO-469-like compounds for the inhibition of p38 MAP kinase, and 4-(indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitriles as protein kinase C theta (PKC θ) inhibitors.
Used in the Synthesis of Vigabatrin Bioisosteres:
C-(1H-INDOL-5-YL)-METHYLAMINE is used in the synthesis of Vigabatrin (V253000) bioisosteres, which are inhibitors of γ-aminobutyric acid aminotransferase (GABA-AT). These compounds have potential applications in the treatment of neurological disorders, such as epilepsy, by modulating the GABAergic system.
Used in the Development of Non-covalent Thrombin Inhibitors:
C-(1H-INDOL-5-YL)-METHYLAMINE is also used as a reactant for the preparation of non-covalent thrombin inhibitors. These inhibitors have potential applications in the prevention and treatment of thrombotic disorders, such as deep vein thrombosis and pulmonary embolism, by targeting the thrombin enzyme and modulating its activity.

InChI:InChI=1/C9H10N2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-5,11H,6,10H2

Upstream product

• 15861-24-2 1H-indole-5-carbonitrile 
• 1075-25-8 indole-5-methanol 
• 10075-50-0 5-bromo-1H-indole 
• 1670-81-1 1H-Indole-5-carboxylic acid 
• 1670-87-7 SD-169 

Downstream Products

• 401907-15-1 1-(1H-indol-5-ylmethyl)-3-phenethylurea 
• 1239447-45-0 N-((1H-indol-5-yl)methyl)-2-(3-benzoylphenyl)propanamide 
• 1235891-82-3 1-[1-(4-fluorophenyl)-1H-indol-5-yl]methanamine 
• 1385840-65-2 C₂₄H₂₅BrN₆O 
• 1385841-79-1 C₂₅H₁₉BrN₄O₄S 
• 267875-62-7 tert-butyl ((1H-indol-5-yl)methyl)carbamate 
• 15861-24-2 1H-indole-5-carbonitrile 
• 1196-69-6 1H-indole-5-carboxaldehyde 
• 1418283-43-8 N-[(indol-5-yl)methyl]-2-(2,4-dichlorophenoxy)propanamide 

Relevant articles and documents

Effects of ruthenium hydride species on primary amine synthesis by direct amination of alcohols over a heterogeneous Ru catalyst

Heterogeneously catalysed synthesis of primary amines by direct amination of alcohols with ammonia has long been an elusive goal. In contrast to reported Ru-based catalytic systems, we report that Ru-MgO/TiO2 acts as an effective heterogeneous catalyst for the direct amination of a variety of alcohols to primary amines at low temperatures of ca. 100 °C without the introduction of H2 gas. The present system could be applied to a variety of alcohols and provides an efficient synthetic route for 2,5-bis(aminomethyl)furan (BAMF), an attention-getting biomonomer. The high catalytic performance can be rationalized by the reactivity tuning of Ru-H species using MgO. Spectroscopic measurements suggest that MgO enhances the reactivity of hydride species by electron donation from MgO to Ru.

A State-of-the-Art Heterogeneous Catalyst for Efficient and General Nitrile Hydrogenation

Cobalt-doped hybrid materials consisting of metal oxides and carbon derived from chitin were prepared, characterized and tested for industrially relevant nitrile hydrogenations. The optimal catalyst supported onto MgO showed, after pyrolysis at 700 °C, magnesium oxide nanocubes decorated with carbon-enveloped Co nanoparticles. This special structure allows for the selective hydrogenation of diverse and demanding nitriles to the corresponding primary amines under mild conditions (e.g. 70 °C, 20 bar H2). The advantage of this novel catalytic material is showcased for industrially important substrates, including adipodinitrile, picolinonitrile, and fatty acid nitriles. Notably, the developed system outperformed all other tested commercial catalysts, for example, Raney Nickel and even noble-metal-based systems in these transformations.

Selective Hydrogenation of Nitriles to Primary Amines by using a Cobalt Phosphine Catalyst

A general procedure for the catalytic hydrogenation of nitriles to primary amines by using a non-noble metal-based system is presented. Co(acac)3 in combination with tris[2-(dicyclohexylphosphino)ethyl]phosphine efficiently catalyzes the selective hydrogenation of a wide range of (hetero)aromatic and aliphatic nitriles to give the corresponding amines.