5877-58-7

Basic information

• Product Name: N-benzylidene-m-toluidine
• Synonyms: N-benzylidene-m-toluidine;3-Methyl-N-(phenylmethylene)benzenamine;N-Benzylidene-3-methylaniline
• CAS NO: 5877-58-7
• Molecular Formula: C₁₄H₁₃N
• Molecular Weight: 195.25972
• EINECS: 227-548-5
• Mol File: 5877-58-7.mol
• Article Data: 67

Chemical Properties

• Melting Point: 31°C
• Boiling Point: 321.94°C (rough estimate)
• Flash Point: 148.4 °C
• Appearance: /
• Density: 1.0390
• Vapor Pressure: 0.000244mmHg at 25°C
• Refractive Index: 1.6353
• PKA: 3.33±0.50(Predicted)
• CAS DataBase Reference: N-benzylidene-m-toluidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzylidene-m-toluidine(5877-58-7)
• EPA Substance Registry System: N-benzylidene-m-toluidine(5877-58-7)

Safety Data

• Hazardous Substances Data: 5877-58-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H13N/c1-12-6-5-9-14(10-12)15-11-13-7-3-2-4-8-13/h2-11H,1H3/b15-11+

Upstream product

• 99-08-1 1-methyl-3-nitrobenzene 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 108-44-1 1-amino-3-methylbenzene 
• 538-51-2 benzylidene phenylamine 
• 100-46-9 benzylamine 

Downstream Products

• 2272-45-9 benzal-p-toluidine 
• 87797-61-3 7-methyl-2,4-diphenylquinoline 
• 1453874-93-5 methyl 4-(2-methoxy-2-oxoethyl)-5-phenyl-1-(m-tolyl)-1H-pyrrole-3-carboxylate 
• 1442652-03-0 2,3,5-triphenyl-1-(m-tolyl)-1H-pyrrole 
• 1438900-70-9 N⁴,N^4'-dibenzyl-2,2'-dimethyl-[1,1'-biphenyl]-4,4'-diamine 
• 1394854-64-8 3-(m-tolylamino)-5-phenyl-1-m-tolyl-1H-pyrrol-2(5H)-one 

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.

Rhodium catalyzed multicomponent dehydrogenative annulation: one-step construction of isoindole derivatives

A strategy for one-pot synthesis of isoindoles is describedviaa catalytic multicomponent dehydrogenative annulation of diarylimines, vinyl ketones and simple amines. In the presence of a rhodium catalyst and Cu oxidant, four C-H and two N-H bonds are activated along with the formation of one new C-C and two new C-N bonds, leading to a series of isoindole derivatives in good to very high isolated yields.

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.