N-Benzylideneaniline

Base Information

• Chemical Name: N-Benzylideneaniline
• CAS No.: 538-51-2
• Molecular Formula: C13H11N
• Molecular Weight: 181.237
• Hs Code.: 2925290090
• European Community (EC) Number: 208-694-9
• NSC Number: 736
• UNII: 09N8O50V91,M1JG410QVC
• DSSTox Substance ID: DTXSID101020626,DTXSID10870599,DTXSID30871760
• Nikkaji Number: J380.890D,J95.738K
• Wikidata: Q818455,Q27283343
• ChEMBL ID: CHEMBL1256376
• Mol file: 538-51-2.mol

Synonyms:N-Benzylideneaniline;538-51-2;Benzylideneaniline;(E)-N-Benzylideneaniline;BENZALANILINE;N,1-diphenylmethanimine;N-(phenylmethylene)benzenamine;N-Benzylidenaniline;Benzaldehyde anil;Aniline, N-benzylidene-;N-Benzalaniline;1750-36-3;Diphenylimine;Benzenamine, N-(phenylmethylene)-;N-(phenylmethylidene)aniline;cis-Benzylideneaniline;trans-Benzylideneaniline;Phenyl(benzylidene)amine;Benzylideneaniline [MI];Benzylideneaniline, (Z)-;N-(Phenylmethylidene)benzenamine;33993-35-0;N-((E)-Benzylidene)phenylamine;Benzenamine, N-(phenylmethylene)-, (Z)-;NSC 736;NSC-736;Benzylidene-phenyl-amine;UNII-M1JG410QVC;M1JG410QVC;UNII-09N8O50V91;Benzenamine, N-(phenylmethylene)-, (N(Z))-;Benzenamine, N-(phenylmethylene)-, [N(E)]-;Aniline, N-benzylidene- (8CI);N-[(E)-Phenylmethylidene]aniline;EINECS 208-694-9;09N8O50V91;(Benzylidene)phenylamine;AI3-01538;N-Phenylbenzenemethanimine;N-[Phenylmethylidene]aniline #;N-phenylbenzaldimine;MFCD00003027;N-benzylidene aniline;(Z)-benzylideneaniline;N-phenylbenzylideneamine;Maybridge4_003619;(Z)-N-Benzylideneaniline;Benzaldehyde N-phenylimine;N-Benzylideneaniline, 99%;N-((E)-Benzylidene)aniline;SCHEMBL59999;(E)-N,1-diphenylmethanimine;(1E)-N,1-diphenylmethanimine;Benzylideneaniline ((E)-form);Benzylideneaniline ((Z)-form);NSC736;N-(Phenylmethylene)benzen-amine;CHEMBL1256376;SCHEMBL13084384;DTXSID10870599;DTXSID30871760;DTXSID101020626;HMS1531E11;(NE)-N-(phenylmethylidene)aniline;STL194006;AKOS004910138;AKOS022173555;BENZYLIDENEANILINE Z-FORM [MI];benzenamine, N-[(1E)-phenylmethylene]-;B1034;CS-0066669;FT-0693050;EN300-16168;D73345;EN300-1664019;A928954;Q818455;Q27283343;Z54089727;F8880-7366

Chemical Property of N-Benzylideneaniline

Chemical Property:

• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 52-54 °C
• Refractive Index: 1.55
• Boiling Point: 300 °C at 760 mmHg
• PKA: 3.23±0.30(Predicted)
• Flash Point: 127.174 °C
• PSA: 12.36000
• Density: 0.95 g/cm³
• LogP: 3.43720
• Water Solubility.: Soluble in water (partly), methanol, chloroform, alcohol, and acetic anhydride.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 181.089149355
• Heavy Atom Count: 14
• Complexity: 174

Purity/Quality:

97% ^*data from raw suppliers

N-Benzylideneaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: C1=CC=C(C=C1)C=NC2=CC=CC=C2
• Uses: N-Benzylideneaniline is an additional stain which is used in various immunoassays including flow cytometry, immunofluorescense, immunohistochemistry, and other applications.

Technology Process of N-Benzylideneaniline

There total 436 articles about N-Benzylideneaniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

nitrobenzene (98-95-3,26969-40-4) + benzyl alcohol (100-51-6,185532-71-2) → benzylidene phenylamine (538-51-2) + benzaldehyde (100-52-7)

Guidance literature:

With α,α,α-trifluorotoluene; titanium(IV) oxide; In dodecane; for 3h; under 750.075 Torr; Reagent/catalyst; Darkness; Inert atmosphere; Irradiation;

DOI:10.1016/j.jcat.2019.03.022

Reference yield: 95.0%

aniline (62-53-3) + benzyl alcohol (100-51-6,185532-71-2) → benzylidene phenylamine (538-51-2) + benzaldehyde (100-52-7)

Guidance literature:

With Au/HAP; oxygen; at 100 ℃; for 5h; chemoselective reaction;

DOI:10.1002/anie.200900802

Reference yield: 94.0%

N-Benzylaniline (758640-21-0,103-32-2) → benzylidene phenylamine (538-51-2) + benzaldehyde (100-52-7)

Guidance literature:

With tert.-butylhydroperoxide; Rh₂(cap)4; In acetonitrile; at 20 ℃; for 16h; Product distribution / selectivity;

upstream raw materials:

N-benzyl-N-phenylnitrous amide

N-Benzylaniline

2-Phenyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one

aniline

Downstream raw materials:

1,5-diphenyl-Δ²-1,2,3-triazoline

2-phenylphenanthro[9,10-d]oxazole

1,5-diphenyltetrahydropyrrole-2,3-dione

4-phenyl-2-phenylimino-but-3-enoic acid

Refernces

Catalytic hydrogenation of C{double bond, long}O and C{double bond, long}N bonds via heterolysis of H₂ mediated by metal-sulfur bonds of rhodium and iridium thiolate complexes

10.1016/j.jorganchem.2009.02.018

The research focuses on the catalytic hydrogenation of C@O and C@N bonds using rhodium and iridium thiolate complexes that facilitate the heterolysis of H2. The study investigates the catalytic activity of coordinatively unsaturated rhodium and iridium complexes, Cp*M(PMe3)(SDmp) (1a: M = Rh; 1b: M = Ir), in the hydrogenation of benzaldehyde, N-benzylideneaniline, and cyclohexanone under mild conditions at low temperatures and 1 atm of H2. The key reactants include the metal complexes 1a and 1b, benzaldehyde, N-benzylideneaniline, and cyclohexanone. The experiments involved the generation of M–H/S–H complexes Cp*M(PMe3)(H)(HSDmp) (2a: M = Rh; 2b: M = Ir) through H2 heterolysis by 1a or 1b, which were proposed to transfer both M–H hydride and S–H proton to the substrates. The catalytic reactions were终止 by the dissociation of H-SDmp from the metal centers of 2a and 2b. The analyses used to monitor the reactions and characterize the products included 1H, 13C{1H}, and 31P{1H} NMR spectroscopy, infrared spectroscopy, ESI-MS spectrometry, and elemental analysis. The structure of one of the complexes formed during the reaction was confirmed by X-ray diffraction analysis.