65795-95-1

Basic information

• Product Name: 1H-Indole, 5-nitro-1-(phenylmethyl)-
• CAS NO: 65795-95-1
• Molecular Formula: C15H12N2O2
• Molecular Weight: 252.272
• Mol File: 65795-95-1.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 5-nitro-1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 5-nitro-1-(phenylmethyl)-(65795-95-1)
• EPA Substance Registry System: 1H-Indole, 5-nitro-1-(phenylmethyl)-(65795-95-1)

Safety Data

• Hazardous Substances Data: 65795-95-1(Hazardous Substances Data)

Usage

Structure

Nitro derivative of indole with a nitro group at the 5th position and a phenylmethyl group at the 1st position of the indole ring

Usage

Commonly used in organic synthesis and pharmaceutical research

Biological activities

Exhibits antimicrobial, antifungal, and anticancer properties

Value

Unique structure and diverse biological activities make it a valuable compound in the development of new drugs and bioactive molecules.

Upstream product

• 260783-80-0 N,N,N--trimethyl--1--phenylmethanaminium trifluoromethanesulfonate 
• 6146-52-7 5-nitroindole 
• 501658-21-5 C₁₂H₁₈N₂O₄ 
• 100-39-0 benzyl bromide 
• 1429616-72-7 N-benzyl-N-(2,2-diethoxyethyl)-4-nitroaniline 
• 100-44-7 benzyl chloride 
• 3459-92-5 DBC 

Downstream Products

• 26807-73-8 5-amino-1-benzyl-(1H)-indole 
• 954386-74-4 2-Benzyl-5-nitro-1H-indole 
• 512787-46-1 N-(1-benzyl-1H-indole-5-yl)-methanesulfonamide 

Relevant articles and documents

The palladium-catalyzed direct C3-cyanation of indoles using acetonitrile as the cyanide source

The ligand-free palladium-catalyzed C3-cyanation of indoles via direct C-H functionalization was achieved. This protocol, utilizing CH3CN as a green and readily available cyanide source, produced the desired products in moderate to good yields through transition-metal-catalyzed C-CN bond cleavage. This journal is

Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage

In this paper, we extend the substrate class of Buchwald-Hartwig amination to quaternary ammonium salts. In the presence of Pd(OAc)2 and t-BuXPhos, the coupling of aryl- or arylmethyltrimethylammonium triflates with NH-heteroarenes via C-N bond cleavage affords the desired N-aryl or N-arylmethyl heteroarenes in moderate to excellent yields.

Catalytic Electrophilic C?H Borylation Using NHC?Boranes and Iodine Forms C2-, not C3-, Borylated Indoles

Activation of N-heterocyclic carbene boranes (NHC?BH3) by I2 enables the metal-free catalytic C?H borylation of heteroarenes with formation of H2 as the by-product in a process that uses only bench stable precursors. The borylation of indoles using NHC?BH3/I2 produces C2-borylated indoles exclusively in contrast to other catalytic electrophilic C?H borylation methods. Mechanistic studies indicate that this is due to C3 to C2 boron migration facilitated by the absence of exogenous Br?nsted bases. Thus this C?H borylation methodology proceeds under sufficiently Br?nsted acidic conditions to enable the thermodynamic C2-borylated indole isomer to be formed instead of the C3 borylated-isomer. This demonstrates that electrophilic C?H borylation can be used to access a wider range of borylated regioisomers than reported to date.