17064-77-6

Basic information

• Product Name: N-(2-nitrobenzylidene)aniline
• Synonyms: N-(2-nitrobenzylidene)aniline;2-Nitro-N-phenylbenzenemethanimine;N-Phenyl-2-nitrobenzenemethanimine;N-Phenyl-2-nitrobenzylideneamine
• CAS NO: 17064-77-6
• Molecular Formula: C₁₃H₁₀N₂O₂
• Molecular Weight: 226.2307
• EINECS: 241-126-8
• Mol File: 17064-77-6.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 383.4°Cat760mmHg
• Flash Point: 185.7°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 9.75E-06mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: N-(2-nitrobenzylidene)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-nitrobenzylidene)aniline(17064-77-6)
• EPA Substance Registry System: N-(2-nitrobenzylidene)aniline(17064-77-6)

Safety Data

• Hazardous Substances Data: 17064-77-6(Hazardous Substances Data)

Usage

General Description

N-(2-nitrobenzylidene)aniline is a chemical compound with the molecular formula C13H10N2O2. It is a yellow solid that is commonly used as a pH indicator and in the production of dyes and pigments. N-(2-nitrobenzylidene)aniline is also known for its use in the synthesis of other organic compounds, such as azo dyes and pharmaceuticals. N-(2-nitrobenzylidene)aniline is considered to be a hazardous compound and should be handled with care due to its potential health risks, including skin and eye irritation and possible carcinogenic effects. It is important to use proper safety precautions and handling procedures when working with this chemical.

InChI:InChI=1/C13H10N2O2/c16-15(17)13-9-5-4-6-11(13)10-14-12-7-2-1-3-8-12/h1-10H/b14-10+

Upstream product

• 612-25-9 2-Nitrobenzyl alcohol 
• 62-53-3 aniline 
• 17064-86-7 N-(2-nitrobenzylidene)-4-nitroaniline 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 10389-64-7 5-methyl-4-(2-nitro-benzylidene)-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 102303-79-7 bis<4'-(3'-methyl-1'-phenylpyrazolin-5-one)yl>-2-nitrophenyl-methane 
• 27126-08-5 2-nitroso-benzoic acid anilide 
• 20887-06-3 N-(2-aminobenzyl)aniline 
• 109772-87-4 2-(2-nitrophenyl)-2-phenylaminoacetonitrile 
• 612-41-9 2-nitrocinnamic acid 
• 103582-31-6 3-(2-nitrophenyl)-2-carboxy-2-propenoic acid 
• 65814-60-0 (E)-N-phenyl-2-(phenyldiazenyl)benzamide 
• 93-98-1 N-phenyl benzoyl amide 
• 142-04-1 aniline hydrochloride 
• 1344156-69-9 2-(2-nitrophenyl)-4-phenylquinoline 

Relevant articles and documents

Functional POM-catalyst for selective oxidative dehydrogenative couplings under aerobic conditions

Development of selective and efficient reusable catalytic systems for sustainable chemical production under benign conditions is attractive and received much attention. Herein, we report a rod-shaped octadecyl trimethylammonium functionalized Keggin-type polyoxometalate [PMO12O40] hybrids (OTA-POM) as an efficient heterogeneous catalyst for selective oxidative dehydrogenative couplings under aerobic conditions without any additive or external base. The catalyst recovery and subsequent five successive recyclability studies of hybrid POM confirms the heterogeneous nature of present catalytic system.

Synthesis, antiprotozoal activity, and cheminformatic analysis of 2-phenyl-2h-indazole derivatives

Indazole is an important scaffold in medicinal chemistry. At present, the progress on synthetic methodologies has allowed the preparation of several new indazole derivatives with interesting pharmacological properties. Particularly, the antiprotozoal activity of indazole derivatives have been recently reported. Herein, a series of 22 indazole derivatives was synthesized and studied as antiprotozoals. The 2-phenyl-2H-indazole scaffold was accessed by a one-pot procedure, which includes a combination of ultrasound synthesis under neat conditions as well as Cadogan’s cyclization. Moreover, some compounds were derivatized to have an appropriate set to provide structure-activity relationships (SAR) information. Whereas the antiprotozoal activity of six of these compounds against E. histolytica, G. intestinalis, and T. vaginalis had been previously reported, the activity of the additional 16 compounds was evaluated against these same protozoa. The biological assays revealed structural features that favor the antiprotozoal activity against the three protozoans tested, e.g., electron withdrawing groups at the 2-phenyl ring. It is important to mention that the indazole derivatives possess strong antiprotozoal activity and are also characterized by a continuous SAR.

Synthesis and cytotoxic activity of combretastatin a-4 and 2,3-diphenyl-2h-indazole hybrids

Cancer is the second leading cause of death, after cardiovascular diseases. Different strategies have been developed to treat cancer; however, chemotherapy with cytotoxic agents is still the most widely used treatment approach. Nevertheless, drug resistance to available chemotherapeutic agents is still a serious problem, and the development of new active compounds remains a constant need. Taking advantage of the molecular hybridization approach, in the present work we designed, synthesized, and tested the cytotoxic activity of two hybrid compounds and seven derivatives based on the structure of combretastatin A-4 and 2,3-diphenyl-2H-indazole. Practical modifications of re-ported synthetic protocols for 2-pheny-2H-indazole and 2,3-dipheny-2H-indazole derivatives under microwave irradiation were implemented. The cytotoxicity assays showed that our designed hybrid compounds possess strong activity, especially compound 5, which resulted even better than the reference drug cisplatin against HeLa and SK-LU-1 cells (IC50 of 0.16 and 6.63 μM, respectively), and it had similar potency to the reference drug imatinib against K562 cells. Additionally, in silico and in vitro studies strongly suggest tubulin as the molecular target for hybrid compound 5.