81038-32-6

Basic information

• Product Name: 1-Benzyl-1H-indol-4-ylamine
• Synonyms: 1-Benzyl-1H-indol-4-ylamine;1-benzyl-1H-indol-4-amine
• CAS NO: 81038-32-6
• Molecular Formula: C₁₅H₁₄N₂
• Molecular Weight: 222.28506
• Mol File: 81038-32-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Benzyl-1H-indol-4-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-1H-indol-4-ylamine(81038-32-6)
• EPA Substance Registry System: 1-Benzyl-1H-indol-4-ylamine(81038-32-6)

Safety Data

• Hazardous Substances Data: 81038-32-6(Hazardous Substances Data)

Upstream product

• 35245-93-3 N-benzyl-1H-indol-4-amine 
• 81038-26-8 methyl 2-(4-nitroindole-1-yl)oxyacetate 
• 100-39-0 benzyl bromide 
• 5192-23-4 4-amino-1H-indole 
• 81038-29-1 1-benzyl-4-nitro-1H-indole 
• 81038-27-9 methyl 2-hydroxy-2-(4-nitroindol-1-yl)-acetate 
• 78283-23-5 4-nitro-1-hydroxyindole 
• 4769-97-5 4-nitro-1H-indoIe 

Downstream Products

• 27866-64-4 4-hydroxy-1-(phenylmethyl)-1H-indole 
• 30000-78-3 1-benzyl-4-(benzyloxy)-1H-indole 
• 1186402-01-6 7-benzyl-4-chloro-1,7-dihydro-2H-pyrrolo[2,3-h]quinazoline-2-one 

Relevant articles and documents

Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.

An Unexpected Rearrangement of 4-Alkylaminoindoles

4-Alkylaminoindoles rearrange in good yield to the corresponding 1-alkyl-4-aminoindoles in the presence of 10 molpercent hydrated toluene-p-sulphonic acid in boiling toluene.