780-21-2

Basic information

• Product Name: N-benzylidene-4-chloroaniline
• Synonyms: N-benzylidene-4-chloroaniline;N-(4-Chlorophenyl)benzylideneamine;N-(4-Chlorophenyl)phenylmethanimine;N-Benzylidene-4-chlorobenzenamine;N-Benzylidene-p-chloroaniline;N-BENZYLIDENE-4-CHLOROANILINE, TECH.
• CAS NO: 780-21-2
• Molecular Formula: C₁₃H₁₀ClN
• Molecular Weight: 215.68
• Mol File: 780-21-2.mol
• Article Data: 200

Chemical Properties

• Boiling Point: 342.7 °C at 760 mmHg
• Flash Point: 161.1 °C
• Appearance: /
• Density: 1.08 g/cm³
• Vapor Pressure: 0.000146mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: N-benzylidene-4-chloroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzylidene-4-chloroaniline(780-21-2)
• EPA Substance Registry System: N-benzylidene-4-chloroaniline(780-21-2)

Safety Data

• Hazardous Substances Data: 780-21-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 967, 1985 DOI: 10.1055/s-1985-31406

InChI:InChI=1/C13H10ClN/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-10H/b15-10+

Upstream product

• 100-52-7 benzaldehyde 
• 106-47-8 4-chloro-aniline 
• 861308-74-9 N-(α-bromo-benzyl)-4-chloro-aniline 
• 106-49-0 p-toluidine 
• 62-53-3 aniline 
• 100-51-6 benzyl alcohol 
• 15484-91-0 N-benzylidene-4-ethoxyaniline 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 100-47-0 benzonitrile 
• 100-00-5 4-chlorobenzonitrile 
• 3296-05-7 1-azido-4-chlorobenzene 
• 6554-98-9 trans-4-Hydroxystilbene 
• 94-41-7 benzalacetophenone 
• 140-38-5 N-(4-chlorophenyl)urea 

Downstream Products

• 4508-25-2 8-chloro-9b-methyl-4-phenyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline 
• 125311-40-2 2,6-distyrylpyridine 
• 79113-99-8 2-[1-(4-Chloro-phenyl)-2-oxo-4-phenyl-azetidin-3-yl]-isoindole-1,3-dione 
• 35173-74-1 3,3'-bis-indolyl(phenyl)methane 
• 29940-94-1 B{N(CH₂C₆H₄-4-Cl)(C₆H₅)}3 
• 1013422-78-0 ethyl 5-((4-chlorophenyl)amino)-2-diazo-3-oxo-5-phenylpentanoate 

Relevant articles and documents

Photocatalytic one-pot multidirectional N-alkylation over Pt/D-TiO2/Ti3C2: Ti3C2-based short-range directional charge transmission

Visible-light-induced one-pot, multistep, and chemoselectivity adjustable reactions highlight the economical, sustainable, and green process. Herein, we report Pt nanoparticles dispersed on S and N co-doped titanium dioxide/titanium carbide (MXene) (3%Pt/

Direct synthesis of imines from nitro compounds and biomass-derived carbonyl compounds over nitrogen-doped carbon material supported Ni nanoparticles

The selective synthesis of imines from biomass-derived chemicals over heterogeneous non-noble metal catalysts is of great importance for organic transformation. Herein, non-noble heterogeneous nitrogen-doped carbon supported Ni catalysts (abbreviated as Ni/CN-MgO-T, whereTrepresents the pyrolysis temperature) have been facilely prepared from the simple pyrolysis of Ni precursors and biomass, and Ni/CN-MgO-600 with the smallest size of Ni nanoparticles demonstrated the highest catalytic activity. The reductive coupling of nitroarenes and carbonyl compounds could be performed under mild conditions (80 °C, and 10 bar H2), affording structurally-diverse imines with high to excellent yields (84.2-98.1%). Thanks to the mild reaction conditions, the developed method showed good tolerance to other functional groups such as nitriles, halogen and vinyl groups.

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.