25688-27-1

Basic information

• Product Name: 1H-Indole, 1-(4-nitrophenyl)-
• CAS NO: 25688-27-1
• Molecular Formula: C14H10N2O2
• Molecular Weight: 238.246
• Mol File: 25688-27-1.mol
• Article Data: 70

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 1-(4-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 1-(4-nitrophenyl)-(25688-27-1)
• EPA Substance Registry System: 1H-Indole, 1-(4-nitrophenyl)-(25688-27-1)

Safety Data

• Hazardous Substances Data: 25688-27-1(Hazardous Substances Data)

Usage

Structure

A derivative of indole with a 4-nitrophenyl group attached

Usage

Often used as a building block in the synthesis of biologically active molecules and pharmaceuticals

Color

Pale yellow to orange

Solubility

Sparingly soluble in water, suitable for use in organic synthesis and medicinal chemistry

Medicinal properties

Studied for potential antimicrobial and anticancer properties, highlighting its importance in medicinal chemistry.

Upstream product

• 120-72-9 indole 
• 98-95-3 nitrobenzene 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 
• 350-46-9 4-Fluoronitrobenzene 
• 40899-71-6 1-benzenesulfonylindole 
• 100-00-5 4-chlorobenzonitrile 
• 636-98-6 p-nitrobenzene iodide 
• 586-78-7 para-nitrophenyl bromide 
• 24067-17-2 4-nitrophenylboronic acid 
• 65185-58-2 2-(2-bromophenyl)ethanamine 

Downstream Products

• 1312670-74-8 {[1-(4-nitrophenyl)indol-3-yl]sulfanyl}acetic acid 
• 1312670-90-8 {[1-(4-nitrophenyl)indol-3-yl]sulfonyl}acetic acid 
• 29330-00-5 1-(4-nitrophenyl)-2-phenyl-1H-indole 
• 1094596-07-2 N-{2,2,2-trichloro-1-[1-(4-nitrophenyl)-1H-indol-3-yl]ethyl}trifluoromethanesulfonamide 
• 938018-12-3 4-(1H-indol-1-yl)benzenamine 

Relevant articles and documents

Copper nanoparticle anchored biguanidine-modified Zr-UiO-66 MOFs: a competent heterogeneous and reusable nanocatalyst in Buchwald-Hartwig and Ullmann type coupling reactions

We have designed a functionalized metal-organic framework (MOF) of UiO topology as a support, with an extremely high surface area, adjustable pore sizes and stable crystalline coordination polymeric structure and implanted copper (Cu) nanoparticles thereon. The core three dimensional Zr-derived MOF (UiO-66-NH2) was modified with a biguanidine moiety following a covalent post-functionalization approach. The morphological and physicochemical features of the material were determined using analytical methods such as FT-IR, SEM, TEM, EDX, atomic mapping, XRD and ICP-OES. The SEM and XRD results justified the unaffected morphology of Zr-MOF after structural modifications. The as-synthesized UiO-66-biguanidine/Cu nanocomposite was catalytically explored in the aryl and heteroaryl Buchwald-Hartwig C-N and Ullmann type C-O cross coupling reactions with excellent yields. A library of biaryl amine and biaryl ethers was synthesized over the catalyst under mild and green conditions. Furthermore, the catalyst was isolated by centrifugation and recycled 11 times with no significant copper leaching or change in its activity.

Integrating CuO?Fe2O3 Nanocomposites and Supramolecular Assemblies of Phenazine for Visible-Light Photoredox Catalysis

A photoredox catalytic ensemble consisting of CuO-Fe2O3 nanocomposites and oligomeric derivative of phenazine has been developed. The prepared system acts as an efficient photoredox catalyst for C?N bond formation reaction via SET mechanism under ‘green’ conditions (aerial environment, mixed aqueous media, recyclable), requiring less equivalents of base and amine substrate. The present study demonstrates the significant role of supramolecular assemblies as photooxidants and reductants upon irradiation and their important contribution towards the activation of the metallic centre through energy transfer and electron transfer pathways. The potential of oligomer 4: CuO-Fe2O3 has also been explored for C?C bond formation reactions via the Sonogashira protocol.

Structure Ligation Relationship of Amino Acids for the Amination Cross-Coupling Reactions

The structure ligation relationship (SLR) of amino acids (AAs) for the cross-coupling aminations was examined. While AA ligated C-N cross-couplings under Pd and Ni catalysis were minor or ineffective, the AA ligated Cu-catalyzed C-N cross-couplings were promising particularly with the use of l-methionine. The roles of -NH2, -CO2H, and -S- of l-methionine were investigated and found critical for their ligation efficiency. The finding was compatible with aromatic as well as aliphatic amines including tautomerizable N-heteroarenes.