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:

98%,99%, ^*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:

2-phenylphenanthro[9,10-d]oxazole

1,5-diphenyltetrahydropyrrole-2,3-dione

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

N-phenyl-N-[1-phenyl-1-(pyrid-2-yl)]methylamine

Refernces

• 1、 Parikh, Naisargee,Roy, Sudipta Raha,Seth, Kapileswar,Kumar, Asim,Chakraborti, Asit K.. "'On-Water' Multicomponent Reaction for the Diastereoselective Synthesis of Functionalized Tetrahydropyridines and Mechanistic Insight". . p. 547 - 556. Retrieved 2016.
• 2、 Bao, Yinwei,Wang, Zhuo,Chen, Chen,Zhu, Bolin,Wang, Yuebo,Zhao, Jinghui,Gong, Jinyu,Han, Mengya,Liu, Chang. "Palladium-catalyzed tandem cyclization of fluorinated imidoyl chlorides with 2-bromophenylboronic acid: Synthesis of 6-fluoroalkyl-phenanthridines". . p. 1450 - 1456. Retrieved 2019.
• 3、 Zheng, Deng-Yue,Zhou, Xue-Meng,Mutyala, Suresh,Huang, Xiao-Chun. "High Catalytic Activity of C60Pdn Encapsulated in Metal–Organic Framework UiO-67, for Tandem Hydrogenation Reaction". . p. 19141 - 19145. Retrieved 2018.
• 4、 Connor,Rose. "-". . p. 329,333. Retrieved 1972.
• 5、 Ziarati, Abolfazl,Badiei, Alireza,Mohammadi Ziarani, Ghodsi,Eskandarloo, Hamed. "Simultaneous photocatalytic and catalytic activity of p–n junction NiO@anatase/rutile-TiO2 as a noble-metal free reusable nanoparticle for synthesis of organic compounds". . p. 77 - 82. Retrieved 2017.
• 6、 Cheng, Shengxian,Ma, Xiaoxia,Hu, Yongke,Li, Bindong. "MnO2/graphene oxide: A highly efficient catalyst for imine synthesis from alcohols and amines". . . Retrieved 2017.
• 7、 Li, Maoshuai,Cárdenas-Lizana, Fernando,Keane, Mark A.. "Combined catalytic action of supported Cu and Au in imine production from coupled benzyl alcohol and nitrobenzene reactions". . p. 145 - 153. Retrieved 2018.
• 8、 Lewis, J. W.,Sandorfy, C.. "An infrared study of the photoisomerization of N-benzylideneaniline". . p. 1720 - 1726. Retrieved 1982.
• 9、 Gong, Mingliang,Guo, Chenjun,Luo, Yunjie,Xie, Hongzhen,Zhang, Fangcao. "Hydroborative reduction of amides to amines mediated by La(CH2C6H4NMe2-: O)3". . p. 779 - 791. Retrieved 2022/01/22.
• 10、 Li, Bo,Wang, Yanxin,Chi, Quan,Yuan, Ziliang,Liu, Bing,Zhang, Zehui. "Direct synthesis of imines from nitro compounds and biomass-derived carbonyl compounds over nitrogen-doped carbon material supported Ni nanoparticles". . p. 4464 - 4471. Retrieved 2021/03/15.