4-methoxy-N-phenylaniline

Base Information

• Chemical Name: 4-methoxy-N-phenylaniline
• CAS No.: 1208-86-2
• Molecular Formula: C13H13NO
• Molecular Weight: 199.252
• Hs Code.: 29222990
• European Community (EC) Number: 214-902-9
• NSC Number: 31630
• DSSTox Substance ID: DTXSID70153017
• Nikkaji Number: J29.665A
• Wikidata: Q72489758
• Mol file: 1208-86-2.mol

Synonyms:4-Methoxydiphenylamine;4-methoxy-N-phenylaniline;1208-86-2;N-Phenyl-p-anisidine;(4-Methoxy-phenyl)-phenyl-amine;Benzenamine, 4-methoxy-N-phenyl-;N-Phenyl-4-methoxyaniline;EINECS 214-902-9;MFCD00228649;4-methoxy-N-phenyl-aniline;NSC31630;4-methoxyphenylaniline;Oprea1_627634;SCHEMBL316390;DTXSID70153017;AMY17952;N-(4-Methoxyphenyl)-N-phenylamine;NSC 31630;NSC-31630;AKOS001061312;N-(4-Methoxyphenyl)-N-phenylamine #;CS-W010506;NCGC00325014-01;DS-18561;SY036318;(4-methoxy-phenyl)-phenyl-amine, AldrichCPR;FT-0655814;M2069;EN300-06439;AB01100227-03;A804608;SR-01000393532;J-501425;SR-01000393532-1;Z56926525

Chemical Property of 4-methoxy-N-phenylaniline

Chemical Property:

• Vapor Pressure: 0.000117mmHg at 25°C
• Melting Point: 104.0 to 108.0 °C
• Refractive Index: 1.61
• Boiling Point: 335.8 °C at 760 mmHg
• PKA: 1.47±0.20(Predicted)
• Flash Point: 134.1 °C
• PSA: 21.26000
• Density: 1.11 g/cm³
• LogP: 3.51180
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Very Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 199.099714038
• Heavy Atom Count: 15
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxy-N-phenylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)NC2=CC=CC=C2
• Uses: 4-Methoxy-N-phenylaniline is a metabolite found from pears and apples.

Technology Process of 4-methoxy-N-phenylaniline

There total 173 articles about 4-methoxy-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: 89.0%

bromobenzene (108-86-1,52753-63-6) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Guidance literature:

With C₄₆H₅₈Br₂N₄O₁₀Pd; potassium tert-butylate; In 1,2-dimethoxyethane; at 80 ℃; for 15h; Inert atmosphere; Buchwald-Hartwig amination;

DOI:10.1002/aoc.1731

Reference yield: 89.0%

4-methoxy-aniline (104-94-9) + 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (88284-48-4) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Guidance literature:

With cesium fluoride; In acetonitrile; at 20 ℃; for 10h;

DOI:10.1021/jo0602221

Reference yield: 85.0%

4-methoxy-aniline (104-94-9) + chlorobenzene (108-90-7) → N-(4-methoxyphenyl)phenylamine (1208-86-2) + N,N-diphenyl-4-methoxyaniline (4316-51-2)

Guidance literature:

With potassium tert-butylate; copper(l) iodide; tributylphosphine; In toluene; at 135 ℃; for 10.5h; high pressure;

DOI:10.1039/b308034j

upstream raw materials:

5-methoxy-2-(phenylamino)benzoic acid

bromobenzene

4-methoxyacetanilide

4-methoxy-aniline

Downstream raw materials:

1,2-bis(4-methoxyphenyl)-1,2-diphenylhydrazine

3-chloro-6-[4-(diphenylamino)phenoxy]-1,2,4,5-tetrazine

3,6-bis[4-(diphenylamino)phenoxy]-1,2,4,5-tetrazine

4-hydroxyltriphenylamine

Refernces

• 1、 Das, Pralay,Basu, Basudeb. "Microwave-assisted copper promoted N-arylation of amines with aryl boronic acids/salts on a KF-alumina surface". . p. 2177 - 2184. Retrieved 2004.
• 2、 Pramjit, Songyos,Eiamprasert, Utt,Surawatanawong, Panida,Lertturongchai, Pattida,Kiatisevi, Supavadee. "Carbazole-bridged double D-A dye for efficient dye-sensitized solar cell". . p. 1 - 10. Retrieved 2015.
• 3、 Yang, Jin,Li, Pinhua,Zhang, Yicheng,Wang, Lei. "Dinuclear N-heterocyclic carbene palladium(II) complexes as efficient catalysts for the Buchwald-Hartwig amination". . p. 73 - 78. Retrieved 2014.
• 4、 Chen, Meng-Chi,Lee, Yao-Lin,Huang, Zhi-Xuan,Chen, Deng-Gao,Chou, Pi-Tai. "Tuning Electron-Withdrawing Strength on Phenothiazine Derivatives: Achieving 100 % Photoluminescence Quantum Yield by NO2 Substitution". . p. 7124 - 7130. Retrieved 2020.
• 5、 Kopp, Felix,Sapountzis, Ioannis,Knochel, Paul. "Preparation of polyfunctional amines by the addition of functionalized organomagnesium reagents to nitrosoarenes". . p. 885 - 887. Retrieved 2003.
• 6、 Hartman, Ryan L.,Zaborenko, Nikolay,Jensen, Klavs F.,Naber, John R.,Buchwald, Stephen L.. "Overcoming the challenges of solid bridging and constriction during Pd-catalyzed C-N bond formation in microreactors". . p. 1347 - 1357. Retrieved 2010.
• 7、 Giri, Gaurav,Yang, Lu,Mo, Yiming,Jensen, Klavs F.. "Adding Crystals to Minimize Clogging in Continuous Flow Synthesis". . p. 98 - 105. Retrieved 2019.
• 8、 Ansari, Tharique N.,Taussat, Armand,Clark, Adam H.,Nachtegaal, Maarten,Plummer, Scott,Gallou, Fabrice,Handa, Sachin. "Insights on bimetallic micellar nanocatalysis for buchwald-hartwig aminations". . p. 10389 - 10397. Retrieved 2019.
• 9、 Paul, Piyali,Butcher, Ray J.,Bhattacharya, Samaresh. "Palladium complexes of 2-formylpyridine thiosemicarbazone and two related ligands: Synthesis, structure and, spectral and catalytic properties". . p. 67 - 75. Retrieved 2015.
• 10、 Choudhary, Hemant,Berton, Paula,Gurau, Gabriela,Myerson, Allan S.,Rogers, Robin D.. "Ionic liquids in cross-coupling reactions: liquid solutions to a solid precipitation problem". . p. 2056 - 2059. Retrieved 2018.