2-methyl-N-phenylaniline

Base Information

• Chemical Name: 2-methyl-N-phenylaniline
• CAS No.: 1205-39-6
• Molecular Formula: C13H13 N
• Molecular Weight: 183.253
• Hs Code.: 2921440000
• DSSTox Substance ID: DTXSID00450829
• Nikkaji Number: J29.922G
• Wikidata: Q81985990
• Mol file: 1205-39-6.mol

Synonyms:2-methyl-N-phenylaniline;1205-39-6;2-METHYLDIPHENYLAMINE;Phenyl-o-tolyl-amine;MFCD01318642;2-methyl-N-phenyl-aniline;2-anilinotoluene;Benzenamine, 2-methyl-N-phenyl-;Phenyl o-tolylamine;Tolylphenylaminfarbstoff;N-(2-methylphenyl)aniline;SCHEMBL304152;DTXSID00450829;JTMODJXOTWYBOZ-UHFFFAOYSA-N;AKOS006280476;BENZENAMINE,2-METHYL-N-PHENYL-;DS-6953;SY108419;CS-0152949;S12003;A804533;J-517483

Chemical Property of 2-methyl-N-phenylaniline

Chemical Property:

• Melting Point: 130-140 °C
• Boiling Point: 305 °C(Press: 727 Torr)
• PKA: 0.65±0.20(Predicted)
• PSA: 12.03000
• Density: 1.066±0.06 g/cm3(Predicted)
• LogP: 3.81160
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 183.104799419
• Heavy Atom Count: 14
• Complexity: 161

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Methyl-N-phenylaniline 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1NC2=CC=CC=C2

Technology Process of 2-methyl-N-phenylaniline

There total 85 articles about 2-methyl-N-phenylaniline 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: 99.0%

bromobenzene (108-86-1,52753-63-6) + o-toluidine (95-53-4) → N-phenyl-2-methylaniline (1205-39-6)

Guidance literature:

With (2-phenyl-1H-inden-3-yl)-dicyclohexylphosphinium tetrafluoroborate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate; In 1,2-dimethoxyethane; at 20 - 120 ℃; Inert atmosphere;

DOI:10.1016/j.jorganchem.2010.04.005

Reference yield: 99.0%

2-methylchlorobenzene (95-49-8) + aniline (62-53-3) → N-phenyl-2-methylaniline (1205-39-6)

Guidance literature:

With dichloro(3-chloropyridinyl)(1,3-(diisopropylphenyl)-4,5-bis(dimethylamino)imidazol-2-ylidene)palladium(II); caesium carbonate; In 1,2-dimethoxyethane; at 80 ℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere;

DOI:10.1002/ejoc.201500030

Reference yield: 95.0%

2-Methylphenylboronic acid (16419-60-6) + aniline (62-53-3) → N-phenyl-2-methylaniline (1205-39-6)

Guidance literature:

With potassium carbonate; In water; at 20 ℃;

DOI:10.1016/j.tetlet.2013.07.095

upstream raw materials:

1-methyl-2-nitrobenzene

2-[(2-methylphenyl)amino]benzoic acid

N-(2-methylphenyl)-N-phenylacetamide

N-phenyl-N-o-tolylbenzamide

Downstream raw materials:

N-(2-methylphenyl)-N-phenylacetamide

N-phenyl-N-o-tolylbenzamide

Refernces

• 1、 Yu, Ying,Srogl, Jiri,Liebeskind, Lanny S. "Cu(I)-mediated reductive amination of boronic acids with nitroso aromatics.". . p. 2631 - 2634. Retrieved 2004.
• 2、 Chen, Chengjian,Huang, Rongjuan,Batsanov, Andrei S.,Pander, Piotr,Hsu, Yu-Ting,Chi, Zhenguo,Dias, Fernando B.,Bryce, Martin R.. "Intramolecular Charge Transfer Controls Switching Between Room Temperature Phosphorescence and Thermally Activated Delayed Fluorescence". . p. 16407 - 16411. Retrieved 2018.
• 3、 Takeuchi, Hiroshi,Takano, Katsuyuki,Koyama, Kikuhiko. "Aromatic N-Substitution by Phenylnitrenium Ion. Reactions of Phenyl Azide with Aromatics in the Presence of Trifluoroacetic Acid". . p. 1254 - 1256. Retrieved 1982.
• 4、 Ibrahim, Halliru,Bala, Muhammad Dabai. "Earth abundant metal complexes of donor functionalised N-heterocyclic carbene ligands: synthesis, characterisation and application as amination catalysts". . p. 6986 - 6997. Retrieved 2016.
• 5、 Modha, Sachin G.,Popescu, Mihai V.,Greaney, Michael F.. "Synthesis of Triarylamines via Sequential C-N Bond Formation". . p. 11933 - 11938. Retrieved 2017.
• 6、 Tassone, Joseph P.,Spivak, Gregory J.. "[P,N]-phosphinobenzimidazole ligands in palladium-catalyzed C-N cross-coupling reactions: The effect of the N-substituent of the benzimidazole scaffold on catalyst performance". . p. 57 - 61. Retrieved 2017.
• 7、 Malamidou-Xenikaki, Elizabeth,Spyroudis, Spyros,Tsanakopoulou, Maria. "Studies on the reactivity of aryliodonium ylides of 2-hydroxy-1,4-naphthoquinone: Reactions with amines". . p. 5627 - 5631. Retrieved 2003.
• 8、 Chen, Chen,Yang, Lian-Ming. "Ni(II)-(σ-aryl) complex: A facile, efficient catalyst for nickel-catalyzed carbon-nitrogen coupling reactions". . p. 6324 - 6327. Retrieved 2007.
• 9、 -. "Diphenylamine derivative organic room-temperature phosphorescent compound as well as preparation method and application thereof". Paragraph 0057-0062. . Retrieved 2021/07/24.
• 10、 Wong, Shun Man,Choy, Pui Ying,Zhao, Qingyang,Yuen, On Ying,Yeung, Chung Chiu,So, Chau Ming,Kwong, Fuk Yee. "Design of Benzimidazolyl Phosphines Bearing AlterableP,OorP,N-Coordination: Synthesis, Characterization, and Insights into Their Reactivity". supporting information. p. 2265 - 2271. Retrieved 2021/05/05.