4,4'-Dimethoxydiphenylamine

Base Information

• Chemical Name: 4,4'-Dimethoxydiphenylamine
• CAS No.: 101-70-2
• Molecular Formula: C14H15NO2
• Molecular Weight: 229.279
• Hs Code.: 29222990
• European Community (EC) Number: 202-968-1
• UNII: I912MLM9XT
• DSSTox Substance ID: DTXSID3025093
• Nikkaji Number: J3.596C
• Wikidata: Q27280590
• ChEMBL ID: CHEMBL1586339
• Mol file: 101-70-2.mol

Synonyms:4,4'-DIMETHOXYDIPHENYLAMINE;101-70-2;Bis(4-methoxyphenyl)amine;Di-p-anisylamine;4-Methoxy-N-(4-methoxyphenyl)aniline;Bis(p-anisyl)amine;p,p'-Dimethoxydiphenylamine;Di-p-methoxyphenylamine;Benzenamine, 4-methoxy-N-(4-methoxyphenyl)-;Bis(p-methoxyphenyl)amine;Termofleks A;Bis-(4-methoxy-phenyl)-amine;Bis(p-anisylamine);Termofleks A [Czech];CCRIS 4624;Difenam;4-Biphenylamine, 4,4'-dimethoxy-;N,N-bis(4-Methoxyphenyl)amine;N-(4-Methoxyphenyl)-p-anisidine;EINECS 202-968-1;UNII-I912MLM9XT;I912MLM9XT;MLS000780107;DTXSID3025093;4,4-DIMETHOXYDIPHENYLAMINE;MFCD00014895;Bis (P-Anisylamine);SMR000420290;N,N-di(4-methoxyphenyl)amine;FENAM M;di(4-methoxyphenyl)amine;CBMicro_009168;bis(4-methoxyphenyl) amine;Bis-(4-methoxyphenyl)amine;Cambridge id 5136275;cid_7571;4.4'-dimethoxydiphenylamine;bis-(4-methoxyphenyl)-amine;Oprea1_575517;SCHEMBL39057;4,4''-Dimethoxydiphenylamine;4,4/'-Dimethoxydiphenylamine;Di-(4-methoxy phenyl) amine;DTXCID405093;4,4'-dimethoxy-4-biphenylamin;CHEMBL1586339;N-(4-methoxyphenyl)-p-anisidin;BDBM59023;N-(p-Methoxyphenyl)-p-anisidine;HMS2777G23;SMSF0003645;4,4'-Dimethoxydiphenylamine, 99%;Tox21_202895;GEO-03785;LS-335;STK286087;AKOS003236274;AM84302;CS-W004610;DIMETHOXYDIPHENYLAMINE, 4,4'-;SB66814;4-Methoxy-N-(4-methoxyphenyl)aniline #;NCGC00246401-01;NCGC00260441-01;4-Methoxy-N-(4-methoxyphenyl)benzenamine;AC-22296;CAS-101-70-2;SY007389;TS-00598;BIM-0009069.P001;D0632;FT-0623045;A934216;SR-01000196597;SR-01000196597-1;4,4 inverted exclamation mark -Dimethoxydiphenylamine;Q27280590

Chemical Property of 4,4'-Dimethoxydiphenylamine

Chemical Property:

• Appearance/Colour: silver-grey crystalline solid
• Vapor Pressure: 1.06E-05mmHg at 25°C
• Melting Point: 101-102 °C
• Refractive Index: 1.593
• Boiling Point: 371.1 °C at 760 mmHg
• PKA: 2.16±0.40(Predicted)
• Flash Point: 150.5 °C
• PSA: 30.49000
• Density: 1.126 g/cm³
• LogP: 3.52040
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in methanol. Insoluble in water.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 229.110278721
• Heavy Atom Count: 17
• Complexity: 184

Purity/Quality:

98%min ^*data from raw suppliers

4,4''-Dimethoxydiphenylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 68-40-36/37/38
• Safety Statements: 22-36/37/39-36/37-26-53

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)NC2=CC=C(C=C2)OC
• Uses: 4,4'-Dimethoxydiphenylamine is a diphenylamine derivative used as a chemical additive for cured rubber. 4,4'-Dimethoxydiphenylamine is highly toxic and may potentially induce chromosome abberation. 4,4'-Dimethoxydiphenylamine is a diphenylamine derivative used as a chemical additive for cured rubber. It is used in the synthesis of amine electron donating groups in organic donor-bridge-acceptor dyads in Dye Sensitized Solar Cells (DSSC). 4,4?-Dimethoxydiphenylamine is an electron donor and used in the synthesis of organic nonlinear optical (NLO) chromophores which exhibit high thermal and chemical stability, high degree of non-linearity and transparency. They are used in high performance photonic devices.

Technology Process of 4,4'-Dimethoxydiphenylamine

There total 59 articles about 4,4'-Dimethoxydiphenylamine 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: 96.0%

4-chloromethoxybenzene (623-12-1) + 4-methoxy-aniline (104-94-9) → bis(4-methoxyphenyl)amine (101-70-2)

Guidance literature:

With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3chloro-pyridyl)palladium(II) dichloride; caesium carbonate; In 1,2-dimethoxyethane; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.201102428

Reference yield: 92.0%

4-methoxyphenylboronic acid (5720-07-0) + 4-methoxy-aniline (104-94-9) → bis(4-methoxyphenyl)amine (101-70-2)

Guidance literature:

With potassium carbonate; In water; at 20 ℃; for 5h;

DOI:10.1016/j.tetlet.2014.03.066

Reference yield: 91.0%

4-methoxyphenyllead(IV) triacetate (18649-43-9) + 4-methoxy-aniline (104-94-9) → bis(4-methoxyphenyl)amine (101-70-2)

Guidance literature:

copper(I) acetate; In dichloromethane; for 2h;

DOI:10.1016/S0040-4039(00)99469-3

upstream raw materials:

para-iodoanisole

4-methoxyacetanilide

di-p-anisylnitroxide

acetic acid

Downstream raw materials:

4-benzoyloxy-1-hydroxy-2,2,6,6-tetramethylpiperidine

4,4'-dimethoxydiphenylaminyl radical

di-p-anisylnitroxide

hydrogen bromide

Refernces

• 1、 Ma, Dawei,Cai, Qian,Zhang, Hui. "Mild method for ullmann coupling reaction of amines and aryl halides". . p. 2453 - 2455. Retrieved 2003.
• 2、 Yang, Lin,Zhu, Youqin,Wu, Jianglin,Hu, Bin,Pang, Zhenguo,Lu, Zhiyun,Zhao, Suling,Huang, Yan. "Squaraine dyes containing diphenylamine group: Effects of different type structures on material properties and organic photovoltaic performances". . . Retrieved 2019.
• 3、 Nykaza, Trevor V.,Yang, Junyu,Radosevich, Alexander T.. "PEt3-mediated deoxygenative C–N coupling of nitroarenes and boronic acids". . p. 3248 - 3252. Retrieved 2019.
• 4、 Ando, Shin,Hirota, Yurina,Matsunaga, Hirofumi,Ishizuka, Tadao. "Nickel-catalyzed N-arylation of amines with arylboronic acids under open air". . p. 1277 - 1280. Retrieved 2019.
• 5、 Hori,Mori. "Synthesis of nonsubstituted anilines from molecular nitrogen via transmetalation of arylpalladium complex with titanium-nitrogen fixation complexes". . p. 7651 - 7652. Retrieved 1998.
• 6、 Michinobu, Tsuyoshi,Tsuchida, Eishun,Nishide, Hiroyuki. "3,4'-Bis[bis(t-butyl- and methoxy-phenyl)amino]stilbene bis(cation radical)s and their electrochemical and magnetic properties". . p. 1021 - 1027. Retrieved 2000.
• 7、 McNulty, James,Cheekoori, Sreedhar,Bender, Timothy P.,Coggan, Jennifer A.. "A pronounced anionic effect in the Pd-catalyzed Buchwald-Hartwig animation reaction revealed in phosphonium salt ionic liquids". . p. 1423 - 1428. Retrieved 2007.
• 8、 Chiykowski, Valerie A.,Lam, Brian,Du, Chuan,Berlinguette, Curtis P.. "On how electron density affects the redox stability of phenothiazine sensitizers on semiconducting surfaces". . p. 2547 - 2550. Retrieved 2017.
• 9、 Takahashi, Rina,Kubota, Koji,Ito, Hajime. "Air- And moisture-stable Xantphos-ligated palladium dialkyl complex as a precatalyst for cross-coupling reactions". . p. 407 - 410. Retrieved 2020.
• 10、 Matsuo, Koji,Shichida, Yoshiaki,Nishida, Hiroshi,Nakata, Satsuki,Okubo, Masao. "N-ALKYLATION AND N-ARYLATION OF ANILINES STARTING FROM A MILD N-Mg REAGENT: ITS ACTIVATION CAUSING THE 'N-C' COUPLING TO EXTEND THE UNIFIED STRUCTURE-REACTIVITY RELATIONSHIP". . p. 9 - 17. Retrieved 1994.