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 
• 13381-65-2 α-Bromobenzyl benzoate 
• 108-88-3 toluene 
• 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 
• 3296-05-7 1-azido-4-chlorobenzene 
• 100-47-0 benzonitrile 
• 19865-58-8 N-(4-chlorophenyl)-α-phenylnitrone 
• 536-74-3 phenylacetylene 
• 34918-76-8 N-(4-chlorophenyl)benzimidoyl chloride 

Downstream Products

• 23575-74-8 diethyl {[(4-chlorophenyl)amino](phenyl)methyl}phosphonate 
• 1066-40-6 Trimethylsilanol 
• 106-47-8 4-chloro-aniline 
• 538-49-8 2-[(E)-2-phenylethenyl]pyridine 
• 60301-56-6 6-chloro-2-phenylquinoline 
• 88745-03-3 5-Amino-1-(4-chloro-phenyl)-2-phenyl-1,2-dihydro-pyrrole-3,3,4-tricarbonitrile 
• 2239-92-1 Isopropyl N-4-chlorophenylcarbamate 

Relevant articles and documents

Copper-Catalyzed Intramolecular Amination of C(sp3)-H Bond of Secondary Amines to Access Azacycles

The cross-coupling of C-N bond directly from inert C-H bonds is an ideal approach to synthesize saturated azacycles due to its high efficiency and atom economy. In this article, a copper-catalyzed intramolecular amination via the cross coupling of C(sp3)-H and N-H bonds of secondary amine has been reported, which exhibit excellent chemo- and regioselectivity, extensive substrate scope, and functional group tolerance in good to excellent yield, offering an efficient pathway to build nitrogen-containing heterocycle skeletons.

Sulfated polyborate: A dual catalyst for the reductive amination of aldehydes and ketones by NaBH4

An efficient, quick, and environment-friendly one-pot reductive amination of aldehydes or ketones was developed. In ethanol at 70 °C, a imination catalyzed by sulfated polyborate and further reduced by sodium borohydride yields various amines. The present method has many significant benefits, including a shorter reaction time, excellent yields, and a hassle-free, straightforward experimental process. The reaction has a wide range of applications due to its flexibility, including secondary amine for reductive amination.

Efficient Imine Formation by Oxidative Coupling at Low Temperature Catalyzed by High-Surface-Area Mesoporous CeO2 with Exceptional Redox Property

High-surface-area mesoporous CeO2 (hsmCeO2) was prepared by a facile organic-template-induced homogeneous precipitation process and showed excellent catalytic activity in imine synthesis in the absence of base from primary alcohols and amines in air atmosphere at low temperature. For comparison, ordinary CeO2 and hsmCeO2 after different thermal treatments were also investigated. XRD, N2 physisorption, UV-Raman, H2 temperature-programmed reduction, O2 temperature-programmed desorption, EPR spectroscopy, and X-ray photoelectron spectroscopy were used to unravel the structural and redox properties. The hsmCeO2 calcined at 400 °C shows the highest specific surface area (158 m2 g?1), the highest fraction of surface coordinatively unsaturated Ce3+ ions (18.2 %), and the highest concentration of reactive oxygen vacancies (2.4×1015 spins g?1). In the model reaction of oxidative coupling of benzyl alcohol and aniline, such an exceptional redox property of the hsmCeO2 catalyst can boost benzylideneaniline formation (2.75 and 5.55 mmol (Formula presented.) h?1 based on >99 % yield at 60 and 80 °C, respectively) in air with no base additives. It can also work effectively at a temperature of 30 °C and in gram-scale synthesis. These are among the best results for all benchmark ceria catalysts in the literature. Moreover, the hsmCeO2 catalyst shows a wide scope towards primary alcohols and amines with good to excellent yield of imines. The influence of reaction parameters, the reusability of the catalyst, and the reaction mechanism were investigated.