(1H-Indol-4-yl)methanamine

Base Information

• Chemical Name: (1H-Indol-4-yl)methanamine
• CAS No.: 3468-18-6
• Molecular Formula: C9H10N2
• Molecular Weight: 146.192
• Hs Code.: 2933990090
• European Community (EC) Number: 663-726-2
• NSC Number: 131886
• DSSTox Substance ID: DTXSID00299654
• Nikkaji Number: J3.102.583D
• Wikidata: Q72483021
• Mol file: 3468-18-6.mol

Synonyms:4-Aminomethylindole;3468-18-6;(1H-Indol-4-yl)methanamine;1H-indol-4-ylmethanamine;1h-indole-4-methanamine;4-(Aminomethyl)indole;(1H-Indol-4-ylmethyl)amine;MFCD04973297;(1H-Indol-4-ymetyl)amine;1-(1H-indol-4-yl)methanamine;C-(1H-Indol-4-yl)-methylamine;NSC131886;4-(aminomethyl)-indole;4-aminomethyl-1h-indole;4-(Aminomethyl)indole, 95%;c-(1h-indol-4-yl)methylamine;SCHEMBL2245672;DTXSID00299654;CHEBI:187682;FFBWKPKOXRMLNP-UHFFFAOYSA-N;BBL030315;STK742067;AKOS004122056;AB21262;NSC-131886;AS-39487;PD020356;SY027224;BB 0255223;CS-0039164;FT-0646140;EN300-333061;A822345;J-019710

Chemical Property of (1H-Indol-4-yl)methanamine

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 132℃
• Boiling Point: 335.6 °C at 760 mmHg
• PKA: 17.21±0.30(Predicted)
• Flash Point: 183.3 °C
• PSA: 41.81000
• Density: 1.199 g/cm³
• LogP: 2.32690
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Soluble in ethanol, dimethyl sulfoxide and dimethyl formamide.
• Water Solubility.: DMSO:PBS ( 7.2) (1:1), also sol. in EtOH,DMSO&DMF
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 146.084398327
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

97% ^*data from raw suppliers

4-Aminomethylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C2C=CNC2=C1)CN
• General Description: 4-AMINOMETHYLINDOLE, also known as (1H-indol-4-yl)methanamine, is a key reactant in enantioselective iso-Pictet-Spengler reactions, where it condenses with α-ketoamides to form complex indole-based heterocycles such as 3,3-disubstituted-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinolines. Its use in these reactions enables the synthesis of underexplored indole core structures with high enantioselectivity and yield, highlighting its utility in medicinal chemistry for constructing pharmacologically relevant scaffolds.

Technology Process of (1H-Indol-4-yl)methanamine

There total 4 articles about (1H-Indol-4-yl)methanamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.7%

4-cyanoindole (16136-52-0) → 1H-indole-4-methanamine (3468-18-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Reflux; Inert atmosphere;

DOI:10.1021/jm901291r

Reference yield: 88.0%

4-formyl indole (1074-86-8) → 1H-indole-4-methanamine (3468-18-6)

Guidance literature:

With sodium borohydrid; methylamine; In methanol; water;

Reference yield: 80.0%

4-cyanoindole (16136-52-0) + sodium hydrogencarbonate (144-55-8) → 1H-indole-4-methanamine (3468-18-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran;

upstream raw materials:

4-formyl indole

4-cyanoindole

sodium hydrogencarbonate

Downstream raw materials:

2-(indol-4-ylmethyl)-3,4-dihydroisoquinolinium bromide

N-((1H-indol-4-yl)methyl)-N-(2-(tert-butylamino)-2-oxo-1-phenylethyl)but-2-ynamide

Refernces

Direct and highly enantioselective iso-Pictet-Spengler reactions with α-ketoamides: Access to underexplored indole core structures

10.1021/ol300922b

The study reports the development of direct, one-pot, and highly enantioselective iso-Pictet-Spengler reactions involving the condensation of either (1H-indol-4-yl)methanamine or 2-(1H-Indol-1-yl)ethanamine with various r-ketoamides, followed by the addition of a commercially available chiral silicon Lewis acid. These reactions provide access to 3,3-disubstituted-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinolines and 1,1-disubstituted-1,2,3,4-tetrahydropyrazino[1,2-a]indoles, two underexplored indole-based core structures in medicinal chemistry. The researchers optimized the reactions for different r-ketoamides, achieving high enantioselectivity and yields, demonstrating the practicality and scalability of their method.