6332-77-0

Basic information

• Product Name: N-(2-AMINOETHYL)-N-(4-NITROPHENYL)AMINE
• Synonyms: N-(2-AMINOETHYL)-N-(4-NITROPHENYL)AMINE;N1-(4-NITRO-PHENYL)-ETHANE-1,2-DIAMINE;N1-(4-Nitro-phenyl)-ethane-1;N-(2-Aminoethyl)-4-nitroaniline;1,2-Ethanediamine,N1-(4-nitrophenyl)-;N-(4-nitrophenyl)ethane-1,2-diamine;N1-(4-Nitrophenyl)-1,2-ethanediamine 2HCl
• CAS NO: 6332-77-0
• Molecular Formula: C₈H₁₁N₃O₂
• Molecular Weight: 181.19
• Mol File: 6332-77-0.mol

Chemical Properties

• Melting Point: 152 °C
• Boiling Point: 371.8 °C at 760 mmHg
• Flash Point: 178.6 °C
• Appearance: /
• Density: 1.285 g/cm³
• Vapor Pressure: 1.01E-05mmHg at 25°C
• PKA: 9.23±0.10(Predicted)
• CAS DataBase Reference: N-(2-AMINOETHYL)-N-(4-NITROPHENYL)AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-AMINOETHYL)-N-(4-NITROPHENYL)AMINE(6332-77-0)
• EPA Substance Registry System: N-(2-AMINOETHYL)-N-(4-NITROPHENYL)AMINE(6332-77-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 6332-77-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
N-(2-Aminoethyl)-N-(4-nitrophenyl)amine is used as a building block in chemical research for its unique structure that allows for the exploration of various chemical reactions and the synthesis of complex molecules.
Used in Pharmaceutical Development:
N-(2-Aminoethyl)-N-(4-nitrophenyl)amine is used as a precursor in the development of therapeutic agents, leveraging its chemical properties to contribute to the creation of new medicines.
Used in Material Science:
In the field of material science, N-(2-Aminoethyl)-N-(4-nitrophenyl)amine is used as a component in the synthesis of novel materials, potentially influencing their properties and applications.
Used in Educational Settings:
N-(2-AMINOETHYL)-N-(4-NITROPHENYL)AMINE is also used in educational settings as a teaching aid to demonstrate the principles of organic chemistry, particularly focusing on the effects of functional groups on molecular reactivity.

InChI:InChI=1/C8H11N3O2/c9-5-6-10-7-1-3-8(4-2-7)11(12)13/h1-4,10H,5-6,9H2/p+1

Upstream product

• 6780-13-8 1,2-ethanediamine monohydrate 
• 100-00-5 4-chlorobenzonitrile 
• 107-15-3 ethylenediamine 
• 350-46-9 4-Fluoronitrobenzene 
• 100-02-7 4-nitro-phenol 
• 2576-47-8 2-bromoethylamine hydrobromide 
• 100-01-6 4-nitro-aniline 
• 636-98-6 p-nitrobenzene iodide 
• 497-25-6 dimethylenecyclourethane 
• 586-78-7 para-nitrophenyl bromide 

Downstream Products

• 19201-32-2 N-(4-aminophenyl)-1,2-ethanediamine 
• 61797-08-8 Undec-10-enoic acid (4-nitro-phenyl)-(2-undec-10-enoylamino-ethyl)-amide 
• 71314-28-8 3-[β-(4-nitrophenylamino)-ethyl]-amino-2-hydroxy-1-phenoxypropane 
• 250386-71-1 N-[1-(3-Bromo-phenyl)-meth-(E)-ylidene]-N'-(4-nitro-phenyl)-ethane-1,2-diamine 
• 250386-75-5 N-(4-methyl-benzylidene)-N'-(4-nitro-phenyl)-ethane-1,2-diamine 
• 250386-73-3 N-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-N'-(4-nitro-phenyl)-ethane-1,2-diamine 
• 250386-72-2 N-[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-N'-(4-nitro-phenyl)-ethane-1,2-diamine 
• 1029803-75-5 N-(4,6-Dimethyl-pyridin-2-yl)-N'-(4-nitrophenyl)-ethane-1,2-diamine 
• 1332654-79-1 C₃₆H₅₅N₃O₄ 
• 863485-88-5 N'-(4-nitrophenyl)-N,N-bis(pyridin-2-ylmethyl)ethane-1,2-diamine 
• 717110-29-7 N-[2-(4-nitro-phenylamino)-ethyl]-formamide 
• 250386-77-7 N-[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-N'-(4-nitro-phenyl)-ethane-1,2-diamine 
• 250386-76-6 N-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-N'-(4-nitro-phenyl)-ethane-1,2-diamine 
• 250386-74-4 N-(4-Nitro-phenyl)-N'-[1-phenyl-meth-(E)-ylidene]-ethane-1,2-diamine 

Relevant articles and documents

Dual channel selective fluorescent detection of Al3+ and PPi in mixed aqueous media: DFT studies and cell imaging applications

A new, easily synthesizable chemosensor, DFC-EN-p-Ph-NO2, derived by the Schiff base condensation between 2,6-diformyl-p-cresol and N-(4-nitrophenyl)ethylenediamine, with potential N4O donor atoms was found to act as a dual channel (colori- and fluorimetric) sensor towards Al3+ and PPi emitting at 486 nm (blue region) and 534 nm (green region), respectively in MeOH-H2O (8 : 2, v/v) at pH 7.2 (10 mM HEPES buffer), μ = 0.05 M (LiCl), temperature 25 °C. The binding stoichiometries and formation constants of the sensor towards both Al3+ and PPi were determined by the combined UV-Vis and fluorescence titrations and Job's method, and confirmed by MS (m/z) studies. The corresponding detection limits as calculated by the 3σ method are: 7.55 μM and 3.34 μM. The most interesting part of this study is that on addition of 230 μM PPi to an ensemble of DFC-EN-p-Ph-NO2-Al3+ (20 μM Ligand and 380 μM Al3+) the fluorescence is totally quenched but on further addition of PPi a new emission peak appears at 534 nm. All biologically relevant metal ions and toxic heavy metals did not interfere with the detection of Al3+ ion. Its bio-compatibility with respect to its good solubility in mixed organo-aqueous media (MeOH-H2O) and cell permeability with no or negligible cytotoxicity provide good opportunities towards in vitro cell imaging studies of these ions. In particular, the fluorescent detection of PPi was not interfered by the presence of 400 μM of ATP or Pi although most reported PPi sensors that work in aqueous solution displayed cross-sensitivities toward ATP or Pi. The obvious excellent sensing capability of DFC-EN-p-Ph-NO2 towards PPi and Al3+ was further scrutinized in HCT116 cell lines without much cytotoxicity. The modes of 1 : 1 binding of DFC-EN-p-Ph-NO2 towards Al3+ and PPi were delineated by DFT calculations.

A lysosomal targeting fluorescent probe and its zinc imaging in SH-SY5Y human neuroblastoma cells

Zinc plays a significant role in oxidative balance and central nervous systems. Herein, we reported a highly sensitive fluorescent probe DR, bearing a morpholine group and a BPEN ligand in the naphthalimide fluorophore. Upon Zn2+ binding, DR ex

Synthesis, structural studies and molecular modelling of a novel imidazoline derivative with antifungal activity

Six novel imidazoline derivatives were synthesized and tested in antifungal assays. One of the compounds, N-cyclohexyl-2-imino-3-(4-nitrophenyl)imidazolidine-1-carboxamide showed moderate activity against several clinical strains of Candida albicans. Its structure was solved by X-ray crystallography and its mode of action was deduced using molecular modelling. It was found to be similar to that of fluconazole. The potential for further optimization including SAR of the compound is briefly discussed.

A highly sensitive fluorescent probe for tracking intracellular zinc ions and direct imaging of prostatic tissue in mice

A highly sensitive fluorescent sensor ZnDN was designed, synthesized and used for tracking intracellular zinc ions in various living cells and direct imaging of prostatic tissue in mice. ZnDN was prepared from the heterocyclic-fused naphthalimide fluorophore, and the zinc receptor, N,N-bis(2-pyridylmethyl)ethylenediamine (BPEN). Upon addition of Zn2+ to the solutions of ZnDN, a remarkable fluorescence enhancement was observed, which could be attributed to the photo-induced electron transfer (PET) mechanism. Since ZnDN exhibited high sensitivity toward Zn2+ in phosphate buffer solution, with a limit of detection of 4.0 × 10?9 mol/L, it was further applied for the imaging of exogenous and endogenous Zn2+ in different living cells. Living cells imaging experiments suggested that ZnDN could image the changes of intracellular free zinc ions, and could be used for two-photon imaging. Moreover, flow cytometry suggested that ZnDN could distinguish cancerous prostate cells from normal cells. Animal experiments indicated that ZnDN had the potential in imaging prostate tissue in vivo.

HETEROCYCLIC COMPOUND AS SYK INHIBITOR AND/OR SYK-HDAC DUAL INHIBITOR

A heterocyclic compound as a Syk inhibitor and/or a Syk-HDAC dual inhibitor, or pharmaceutically acceptable salts, prodrugs, deuterated derivatives, hydrates, and solvates thereof. Specifically, the present invention relates to a compound of formula (I), the compound having dual inhibitory activity for Syk and/or Syk-HDAC.

Identification of N-Benzyl 3,5-Dinitrobenzamides Derived from PBTZ169 as Antitubercular Agents

A series of benzamide scaffolds were designed and synthesized by the thiazinone ring opening of PBTZ169, and N-benzyl 3,5-dinitrobenzamides were finally identified as anti-TB agents in this work. 3,5-Dinitrobenzamides D5, 6, 7, and 12 exhibit excellent in vitro activity against the drug susceptive Mycobacterium tuberculosis H37Rv strain (MIC: 0.0625 μg/mL) and two clinically isolated multidrug-resistant strains (MIC 0.016-0.125 μg/mL). Compound D6 displays acceptable safety and better pharmacokinetic profiles than PBTZ169, suggesting its promising potential to be a lead compound for future antitubercular drug discovery.

Synthesis, antitubercular and anticancer activities of p-nitrophenylethyl-enediamine-derived schiff bases

Background: Schiff bases have been greatly studied in biological field due to their wide range of pharmacological activities, such as antitubercular and antitumour. In the search of novel antitubercular agents, several compounds containing pharmacophoric group of ethambutol have been synthesized and evaluated against mycobacteria species causing tuberculosis. In this work, we investigate whether ethylenediamine, Schiff base as well as nitro group together could contribute to the formation of novel molecules with dual biological activities: antitubercular and anticancer. Methods: A series of Schiff bases (3-12) derived from p-nitrophenylethylenediamine (1) as well as N1,N2-bis(4-nitrophenyl)ethane-1,2-diamine (2) were synthetized and assayed for their action against Mycobacterium tuberculosis H37Rv strain and the human tumour cell lines SF-295 (glioblastoma multiforme), HCT-116 (colon adenocarcinoma) and OVCAR-8 (ovarian cancer). Results: Among the compounds that showed antimycobacterial effects, 4 was more active than ethambutol, the antitubercular drug used as positive control. Also, compounds 1, 8, 10 and 12 were able to reduce strongly the viability of the tumour cell lines at 5 gmL-1. Conclusion: According to studies, some modifications on p-nitrophenylethylenediamine (1) were an effective strategy to obtain compounds with antiproliferactive activities. Also, Schiff base 4 proved to be the lead antitubercular compound.

A process for the preparation method of the compound aromatic amines (by machine translation)

The invention discloses a method for preparing aromatic amine compounds, comprising the following steps: under protection of inert gas, with the ratio of the phenolic compound amine according to mole 1:2 - 40 are mixed and dissolved in the solvent, 50 - 140 °C reaction 6 - 15 hours, corresponding to preparing polymerizable aromatic amine compound, and then after treatment to obtain a pure aromatic amine compound. Raw materials of this invention generally are easy, simple operation, substrate and wide range of application, in the absence of catalyst under catalytic conditions of the phenolic compound can be obtained by nucleophilic addition reaction of the corresponding aromatic amine compound, and is suitable for industrial production. The present invention allows the presence of water in the reaction system, can be ammonia or hydrazine hydrate as the substrate, in order to ammonium chloride as a catalyst and a cosolvent, the success of the preparation to obtain a level from phenol hydroxy aromatic primary amino compound. The invention to phenol hydroxy has better selectivity, even if the presence of halogen atoms in the substrate does not affect the occurrence of the reaction. (by machine translation)

Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine-3-carboxamide derivatives

We report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against drug-sensitive/resistant MTB strains, and they have acceptable safety indices against MTB H37Rv with the SI values of 4395 and 1405, respectively. Moreover, N-[2-(piperazin-1-yl)ethyl] moiety was also identified as a potentially alternative linker (compound 31), opening a new direction for further SAR studies.

Integration of Bromine and Cyanogen Bromide Generators for the Continuous-Flow Synthesis of Cyclic Guanidines

A continuous-flow process for the in situ on-demand generation of cyanogen bromide (BrCN) from bromine and potassium cyanide that makes use of membrane-separation technology is described. In order to circumvent the handling, storage, and transportation of elemental bromine, a continuous bromine generator using bromate–bromide synproportionation can optionally be attached upstream. Monitoring and quantification of BrCN generation was enabled through the implementation of in-line FTIR technology. With the Br2 and BrCN generators connected in series, 0.2 mmol BrCN per minute was produced, which corresponds to a 0.8 m solution of BrCN in dichloromethane. The modular Br2/BrCN generator was employed for the synthesis of a diverse set of biologically relevant five- and six-membered cyclic amidines and guanidines. The set-up can either be operated in a fully integrated continuous format or, where reactive crystallization is beneficial, in semi-batch mode.