2272-45-9

Basic information

• Product Name: BENZAL-P-TOLUIDINE
• Synonyms: BENZAL-P-TOLUIDINE;4-Methyl-N-[(E)-phenylmethylidene]aniline;Benzylidene-(4-methylphenyl)-amine;N-benzylidene-p-toluidine;N-benzylidene-4-methylaniline;4-Methyl-N-benzylideneaniline;N-Benzylidene-4-methylbenzenamine;N-Benzylidene-p-methylaniline
• CAS NO: 2272-45-9
• Molecular Formula: C₁₄H₁₃N
• Molecular Weight: 195.26
• EINECS: 218-879-6
• Mol File: 2272-45-9.mol
• Article Data: 246

Chemical Properties

• Melting Point: 35°C
• Boiling Point: 321.94°C (rough estimate)
• Flash Point: 145.001 °C
• Appearance: yellow oily liquid or crystals
• Density: 1.0778 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6353 (estimate)
• PKA: 3.62±0.30(Predicted)
• CAS DataBase Reference: BENZAL-P-TOLUIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZAL-P-TOLUIDINE(2272-45-9)
• EPA Substance Registry System: BENZAL-P-TOLUIDINE(2272-45-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 2272-45-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 4115, 1988 DOI: 10.1016/S0040-4039(00)80431-1

InChI:InChI=1/C14H13N/c1-12-7-9-14(10-8-12)15-11-13-5-3-2-4-6-13/h2-11H,1H3

Upstream product

• 19772-26-0 3-(α-p-toluidino-benzyl)-pentane-2,4-dione 
• 100-52-7 benzaldehyde 
• 106-49-0 p-toluidine 
• 1858-99-7 benzaldehyde p-tolylhydrazone 
• 5405-15-2 N-benzyl-N-(4-methylphenyl)amine 
• 15999-95-8 4-methylphenylbenzimidoyl chloride 
• 99-99-0 1-methyl-4-nitrobenzene 
• 108-88-3 toluene 
• 70-55-3 toluene-4-sulfonamide 
• 100-51-6 benzyl alcohol 
• 2835-06-5 phenylglycin 
• 100-44-7 benzyl chloride 
• 100-46-9 benzylamine 
• 123-91-1 1,4-dioxane 

Downstream Products

• 4390-63-0 N-(phenyl-[2]pyridyl-methyl)-p-toluidine 
• 37552-67-3 3r,4t-diphenyl-1-p-tolyl-azetidin-2-one 
• 13471-34-6 N,N'-di-p-tolylbenzamidine 
• 1859-00-3 N-(4-methylphenyl)benzamidine 
• 27549-67-3 meso-N,N'-bis(4-methylphenyl)-1,2-diphenyl-1,4-ethanediamine 
• 27549-67-3 dl-N,N'-bis(4-methylphenyl)-1,2-diphenyl-1,4-ethanediamine 
• 78604-82-7 α-p-toluidino-deoxybenzoin 
• 5405-15-2 N-benzyl-N-(4-methylphenyl)amine 
• 116028-05-8 3,3,4-triphenyl-1-(p-tolyl)azetidin-2-one 
• 21012-01-1 1,5-diphenyl-5-p-toluidino-pent-1-en-3-one 
• 1089855-57-1 5-Phenyl-1-(4-methylphenyl)-2,3-dioxo-pyrrolidin-4-carbonsaeureethylester 
• 13330-14-8 N-methyl-p-toluidine; hydriodide 
• 97175-45-6 N-benzylidene-N-methyl-p-toluidinium; iodide 
• 51100-97-1 4-methyl-N-[2-(3-methyl-isoxazol-5-yl)-1-phenyl-ethyl]-aniline 

Relevant articles and documents

Highly Stereoselective Synthesis of Saccharin-Substituted β-Lactams via in Situ Generation of a Heterosubstituted Ketene and a Zwitterionic Intermediate as Potential Antibacterial Agents

Highly stereoselective synthesis of saccharin derivatives containing functionalized 2-azetidinone moiety was achieved starting from saccharin as an available precursor. The approach to these valuable heterocyclic scaffolds involves a formal [2π + 2π] cycloaddition between Schiff bases and the saccharinylketene as a novel ketene which was generated in situ and an electrocyclic reaction of a zwitterionic intermediate. The identification of the ketene was confirmed by reaction with the stable free radical TEMPO (TO?). Also, the antimicrobial activities of some new substituted saccharin against nine standard bacteria, four bacteria which were isolated from clinical samples and one yeast, were evaluated.

Highly efficient and selective one-pot tandem imine synthesis via amine-alcohol cross-coupling reaction catalysed by chromium-based MIL-101 supported Au nanoparticles

One-pot tandem synthesis of imines from alcohols and amines is regarded as an effective, economic and green approach under mild conditions. In this work, Au nanoparticles (NPs) dispersed on MIL-101 (Au/MIL-101) were demonstrated as highly active and selective bifunctional heterogeneous catalyst for production of various imine derivatives with excellent yields, via amine-alcohol cross-coupling reaction at 343 K in an open flask under an Ar atmosphere. Various physicochemical techniques, including inductively coupled plasma optical emission spectroscopy (ICP-OES), powder X-ray diffraction (P-XRD), X-ray photoelectron spectroscopy (XPS) transmission electron microscopy (TEM) and N2 adsorption-desorption, were used to characterize of the Au/MIL-101 catalyst. The obtained bifunctional catalyst is highly active and selective towards one-pot imine formation and exhibited the highest TOF (30.15-51.47 h?1) among all the ever-reported MOF-supported Au catalysts. The reaction mechanism of the imine formation from alcohol and amine over Au/MIL-101 catalyst was proposed. Mechanism experiment results demonstrate that Au NPs highly effective in activating oxidation of benzyl alcohol to benzaldehyde while the Lewis acid sites on MIL-101 catalyzed the second condensation step without interfering with the oxidation step. As a result, the excellent catalytic performance of Au/MIL-101 can be ascribed to the synergistic effect between Au NPs with Lewis acid sites in MIL-101.

Copper(i)-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphites

Intramolecular hydroarylation-redox cross-dehydrogenative coupling ofN-propargylanilines with phosphite diesters proceeded in the presence of Cu(i)-catalysts (20 mol%) to selectively give 2-phosphono-1,2,3,4-tetrahydroquinolines in good yields with 100% atomic utilization. P-H and two C-H bonds are activated at once and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.

One-Pot Synthesis of Schiff Bases by Defect-Induced TiO2- x-Catalyzed Tandem Transformation from Alcohols and Nitro Compounds

Schiff bases that are generally formed from condensation reactions of aldehydes (or ketones) and amino groups could also be produced by a photodriven one-pot tandem reaction between alcohols and nitro compounds, in our case. Herein, TiO2-x porous cages derived from NH2-MIL-125 by a self-sacrificing template route are used to study the organic transformation and exhibit 100% conversion efficiency of nitrobenzene and 100% selectivity for Schiff bases in the system of benzyl alcohol (5 mL) and nitrobenzene (41 μL) upon light irradiation, but hydrogen by dehydrogenation of benzyl alcohol cannot be detected. Successful occurrence of the organic transformation is mainly attributed to Ti(III)-oxygen vacancy associates. Surface oxygen vacancy-related Ti(III) sites are responsible for binding with nitro groups, and low-coordinated Ti5c sites selectively adsorb hydroxyl groups of benzyl alcohol. The Ti(III) and oxygen vacancy associates capture photogenerated electrons for achievement of multielectron reduction of nitrobenzene and the subsequent Schiff base condensation reaction with the as-formed benzaldehyde.

Biorenewable carbon-supported Ru catalyst for: N -alkylation of amines with alcohols and selective hydrogenation of nitroarenes

Herein, we developed a renewable carbon-supported Ru catalyst (Ru/PNC-700), which was facilely prepared via simple impregnation followed by the pyrolysis process. The prepared Ru/PNC-700 catalyst demonstrated remarkable catalytic activity in terms of conversion and selectivity towards N-alkylation of anilines with benzyl alcohol and chemoselective hydrogenation of aromatic nitro compounds. In addition, local anesthetic pharmaceutical agents (e.g., butamben and benzocaine), including key drug intermediates, were synthesized in excellent yields under mild conditions and in the presence of water as a green solvent. Moreover, the prepared Ru/PNC-700 catalyst could be easily recovered and reused up to five times without any apparent loss in activity and selectivity.