4085-18-1

Usage

Uses

Used in Chemical Manufacturing:
3-Nitrobiphenyl-4-ylamine is used as a key intermediate in the production of dyes and pigments, contributing to the coloration and stability of various products in the chemical industry. Its presence in these compounds is essential for achieving desired color properties and performance characteristics.
Used in Industrial Chemical Production:
Beyond dyes and pigments, 3-Nitrobiphenyl-4-ylamine serves as a precursor in the synthesis of other industrial chemicals. Its unique structure allows for the creation of a range of chemical products that are utilized across different sectors, including plastics, coatings, and textiles.
However, due to its toxic and potentially harmful properties, 3-Nitrobiphenyl-4-ylamine is listed as a hazardous substance by regulatory authorities. This classification underscores the need for stringent safety measures and handling protocols to mitigate the health risks associated with exposure to 3-Nitrobiphenyl-4-ylamine.

InChI:InChI=1/C12H10N2O2/c13-11-7-6-10(8-12(11)14(15)16)9-4-2-1-3-5-9/h1-8H,13H2

Upstream product

• 858005-39-7 N-(3-nitro-biphenyl-4-yl)-toluene-4-sulfonamide 
• 78843-20-6 3,4-dinitro-1,1^,-biphenyl 
• 91331-25-8 4-chloro-3-nitro-1,1'-biphenyl 
• 7664-41-7 ammonia 
• 20691-72-9 4-iodo-2-nitroaniline 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 875-51-4 4-Bromo-2-nitroaniline 
• 833486-94-5 4-amino-3-nitrophenylboronic acid pinacol ester 
• 88-74-4 2-nitro-aniline 
• 100-63-0 phenylhydrazine 
• 92-67-1 4-phenylalanine 
• 4075-79-0 4-phenylacetanilide 
• 65690-69-9 N-([1,1'-biphenyl]-4-yl)-4-methylbenzenesulfonamide 

Downstream Products

• 20028-74-4 1-oxy-7-phenyl-benzo[e][1,2,4]triazin-3-ylamine 
• 860203-21-0 8-nitro-4,6-diphenyl-quinoline 
• 2113-58-8 3-nitro-1,1'-biphenyl 
• 83821-09-4 4-N-(Benzoylamino)-3-nitrobiphenyl 
• 83821-11-8 4-Nitro-N-(3-nitro-biphenyl-4-yl)-benzamide 
• 92060-44-1 6-phenyl-quinoxaline 
• 85877-63-0 2,3,6-triphenylquinoxaline 
• 403599-65-5 2-hydroxy-N-(3-nitro-biphenyl-4-yl)-benzamide 
• 96548-28-6 7-phenyl-3-chloro-3,4-dihydro-1-hydroxycarbostyril 
• 1352637-92-3 (3-nitrobiphenyl-4-yl)-(3,4,5-trimethoxybenzyl)amine 
• 1352637-76-3 N-(3-aminobiphenyl-4-yl)-3,4,5-trimethoxybenzamide 
• 1352637-79-6 N-(3-acetylaminobiphenyl-4-yl)-3,4,5-trimethoxybenzamide 
• 1352637-95-6 3,4,5-trihydroxy-N-(3-nitrobiphenyl)benzamide 
• 1352637-97-8 3,4-dihydroxy-N-(3-nitrobiphenyl-4-yl)benzamide 

Relevant academic research and scientific papers

The Curious Case of a Phenylated Guanidinoquinoline Ligand: Synthesis, Complexes and ATRP Properties of DMEG6phqu

In previous studies, copper halide complexes of the guanidinoquinoline (GUAqu) ligands 1,3-dimethyl-N-(quinolin-8-yl)-imidazolidin-2-imine (DMEGqu) and 1,1,3,3-tetramethyl-2-(quinolin-8-yl)-guanidine (TMGqu) were successfully implemented in atom transfer radical polymerization (ATRP) and could be further enhanced by introduction of alkyl substituents at C6 position of the quinoline backbone. Herein, the ligand DMEG6phqu is presented. The quinoline backbone of this ligand is equipped with a phenyl substituent at C6 position. This study deals with the influence of the phenyl substituent on solubility and molecular structural properties of DMEG6phqu CuI and CuII bromide complexes. In contrast to previously reported systems, the CuIBr complex of DMEG6phqu crystallizes as a trigonal coordinated monochelate complex. However, NMR and UV/Vis spectroscopic experiments indicate that DMEG6phqu forms a bischelate species in solution. The influence of the substituent on the complex redox potential and ATRP equilibrium constant KATRP is discussed. In contrast to expectations, it turned out that copper halide complexes of DMEG6phqu are completely insoluble in the apolar monomer styrene. However, ATRP kinetics were performed in solution and the results are compared to previous studies.

Synthesis and biological evaluation of N-biphenyl-nicotinic based moiety compounds: A new class of antimitotic agents for the treatment of Hodgkin Lymphoma

We previously demonstrated that some N-biphenylanilides caused cell-cycle arrest at G2/M transition in breast cancer cells. Among them we choose three derivatives, namely PTA34, PTA73 and RS35 for experimentation in solid tumor cell lines, classical Hodgkin Lymphoma (cHL) cell lines and bona fide normal cell lines. Almost all tumor cells were sensitive to compounds in the nanomolar range whereas, they were not cytotoxic to normal ones. Interestingly the compounds caused a strong G2/M phase arrest in cHL cell lines, thus, here we investigated whether they affected the integrity of microtubules in such cells. We found that they induced a long prometaphase arrest, followed by induction of apoptosis which involved mitochondria. PTA73 and RS35 induced the mitotic arrest through the fragmentation of microtubules which prevented the kinethocore-mitotic spindle interaction and the exit from mitosis. PTA34 is instead a tubulin-targeting agent because it inhibited the tubulin polymerization as vinblastine. As such, PTA34 maintained the Cyclin B1-CDK1 regulatory complex activated during the G2/M arrest while inducing the inactivation of Bcl-2 through phosphorylation in Ser70, the degradation of Mcl-1 and a strong activation of BIML and BIMS proapoptotic isoforms. In addition PTA34 exerted an antiangiogenic effect by suppressing microvascular formation.

Synthesis of tetranuclear complex of Pd(II) with thiosemicarbazone ligands derived from 2-quinolone and its catalytic evaluation in Suzuki–Miyaura-type coupling reactions and alkoxylation of chloroquinolines

A tetranuclear palladium(II) complex [(Pd(H-6MOQtsc-Ph))4] was obtained from the reaction between 6-methyl-2-oxo-1,2-dihydroquinoline-3-carboxaldehyde-4(N)-phenylthiosemicarbazone [H2-6MOQtsc-Ph] and K2[PdCl4]. The ligand and the Pd(II) complex were characterized by Fourier transform infrared spectroscopy (FT-IR), UV–visible and 1H NMR spectroscopy. X-ray diffraction studies confirmed the tetrameric nature of the complex with the coordination of ligand through quinolone carbonyl, azomethine nitrogen and thiolate sulfur atoms, and the fourth site is occupied by 2-quinolone nitrogen atom of the adjacent ligand. The synthesized complex was tested as catalyst in Suzuki–Miyaura coupling reaction between various chloroquinoline derivatives with phenylboronic acid. The reactions afforded unexpected C-alkoxylated (C-O coupling) products instead of more expected C-arylated (C-C coupling) products in the respective alcoholic mediums. However, the reactions with traditional aryl halides probed with very good yield of the corresponding C-C coupling products.

Organic compound and organic electroluminescent device containing same

The invention relates to an organic compound, which is characterized by having a structure as shown in (1), wherein L1 and L2 are respectively and independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group or a substituted or unsubstituted C3-C30 heteroarylene group; Arl and Ar2 are respectively and independently selected from a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group; R is halogen, a cyano group, an alkyl group, a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group; and n represents an integer of 0-3.

Tetranuclear Palladacycles of 3-Acetyl-7-methoxy-2 H-chromen-2-one Derived Schiff Bases: Efficient Catalysts for Suzuki-Miyaura Coupling in an Aqueous Medium

Tetranuclear organopalladium(II) complexes 1-3 and mononuclear complex 4 have been synthesized by the complexation of 3-acetyl-7-methoxy-2H-chromen-2-one derived Schiff bases with potassium tetrachloropalladate K2[PdCl4]. Structural confirmation for the complexes (1-3) has been achieved by single-crystal X-ray diffraction analysis. The ligands are found to bind with the palladium ion through its azomethine nitrogen, thiolate sulfur, and C4 carbon atom of the coumarin moiety subsequent to C-H activation. The monomeric nature of complex 4 was confirmed from its mass spectroscopic data. In complex 4, coordination occurred via the lactone oxygen, azomethine nitrogen, and thiolate sulfur atoms. Computational study has been used to determine the optimized molecular structures of the complexes. An explanation on the energies of their highest occupied and lowest unoccupied molecular orbital levels and their electronic spectra has also been provided on the basis of the theoretical calculations. A systematic study of the application of these complexes as catalysts in Suzuki-Miyaura coupling (SMC) has been done with different aryl halides and phenyl boronic acid in an aqueous medium. Optimization of the reaction indicated that complex 2 exhibits greater efficiency than other complexes. An appreciable yield of the coupled products was observed with the minimum use of catalyst (μmol), and the C-C coupling has been confirmed by GC/GC-MS. An interesting result of our catalyst is the coupling of four different chloroquinolines with phenyl boronic acid to afford the coupled products in good yields.

Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines

An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.

Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones

A fast and effective one-pot tandem process that generates Heck coupled products from readily available anilines via stable aryl diazonium tosylate salts was developed. The mild and simple procedure involves rapid formation of aryl diazonium salts using a polymer-supported nitrite reagent and p-tosic acid, followed by a base-free Heck-Matsuda coupling with acrylates and styrenes. Using 2-nitroanilines as substrates, the one-pot tandem process was extended for the direct synthesis of 3,4-dihydroquinolin-2-ones. In this case, following diazotization and Heck-Matsuda coupling to give methyl cinnamates, addition of hydrogen and reutilization of the palladium catalyst for reduction of the nitro group and hydrogenation of the alkene resulted in efficient formation of 3,4-dihydroquinolin-2-ones. The synthetic utility of this one-pot, four-stage process was demonstrated with the five-pot synthesis of a quinolinone-based sodium ion channel modulator.

NOVEL COLOR CONVERTER

Color converter comprising at least one polymer and at least one organic fluorescent dye comprising at least one structural unit of the formula (I) where the structural unit may be mono- or polysubstituted by identical or different substituents and where one or more CH groups of the six-membered ring of the benzimidazole structure shown may be replaced by nitrogen.

CoPc-catalyzed selective radical arylation of anilines with arylhydrazines for synthesis of 2-aminobiaryls

CoPc-catalyzed selective radical arylation of anilines with arylhydrazines to afford 2-aminobiaryls in moderate to good yields is described. This journal is the Partner Organisations 2014.

Discovery of potent, isoform-selective inhibitors of histone deacetylase containing chiral heterocyclic capping groups and a N-(2-aminophenyl)benzamide binding unit

The synthesis of a novel series of potent chiral inhibitors of histone deacetylase (HDAC) is described that contain a heterocyclic capping group and a N-(2-aminophenyl)benzamide unit that binds in the active site. In vitro assays for the inhibition of HDAC1, HDAC2, HDAC3-NCoR1, and HDAC8 by the N-(2-aminophenyl)benzamide 24a gave respective IC50 values of 930, 85, 12, and 4100 nM, exhibiting class I selectivity and potent inhibition of HDAC3-NCoR1. Both imidazolinone and thiazoline rings are shown to be effective replacements for the pyrimidine ring present in many other 2-(aminophenyl) benzamides previously reported, an example of each ring system at 1 μM causing an increase in histone H3K9 acetylation in the human cell lines Jurkat and HeLa and an increase in cell death consistent with induction of apoptosis. Inhibition of the growth of MCF-7, A549, DU145, and HCT116 cell lines by 24a was observed, with respective IC50 values of 5.4, 5.8, 6.4, and 2.2 mM.