3-Methoxydiphenylamine

Base Information

• Chemical Name: 3-Methoxydiphenylamine
• CAS No.: 101-16-6
• Molecular Formula: C13H13NO
• Molecular Weight: 199.252
• Hs Code.: 29222990
• European Community (EC) Number: 202-921-5
• DSSTox Substance ID: DTXSID10143614
• Nikkaji Number: J71.625A
• Wikidata: Q72489761
• Mol file: 101-16-6.mol

Synonyms:3-Methoxydiphenylamine;101-16-6;3-methoxy-n-phenylaniline;N-Phenyl-m-anisidine;Benzenamine, 3-methoxy-N-phenyl-;EINECS 202-921-5;N-phenyl-3-methoxyaniline;3-methoxy diphenylamine;N-(3-Methoxyphenyl)-N-phenylamine;N-phenyl-m-anisidin;MFCD00008383;3-methoxydiphenylamin;3-Methoxydiphenylamine, 98%;BIDD:GT0233;SCHEMBL917608;MKASXAGBWHIGCF-UHFFFAOYSA-;DTXSID10143614;n(3-methoxyphenyl)-n-phenylamine;STR04774;AKOS000121435;N-(3-Methoxyphenyl)-N-phenylamine #;CS-W010505;AC-22498;AM20080714;FT-0631533;M1135;EN300-21118;W-108925

Chemical Property of 3-Methoxydiphenylamine

Chemical Property:

• Appearance/Colour: Buff color powder form
• Vapor Pressure: 0.000173mmHg at 25°C
• Melting Point: 72-74 °C
• Refractive Index: 1.61
• Boiling Point: 329.8 °C at 760 mmHg
• Flash Point: 132 °C
• PSA: 21.26000
• Density: 1.11 g/cm³
• LogP: 3.51180
• Storage Temp.: room temp
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 199.099714038
• Heavy Atom Count: 15
• Complexity: 177

Purity/Quality:

99.9% ^*data from raw suppliers

3-Methoxydiphenylamine ^*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:

• Canonical SMILES: COC1=CC=CC(=C1)NC2=CC=CC=C2
• Uses: 3-Methoxydiphenylamine can be used in the preparation of 3- methoxydiphenylamine-4-diazonium salts (MDP-4-DS) and the corresponding diazoresins. Diazonium salts and diazoresins find applications in dyes, stains, indicators, general laboratory use, and industrial applications.

Technology Process of 3-Methoxydiphenylamine

There total 50 articles about 3-Methoxydiphenylamine 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: 98.0%

1-chloro-3-methoxy-benzene (2845-89-8) + aniline (62-53-3) → 3-methoxy-N-phenylaniline (101-16-6)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; sodium t-butanolate; 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane; In toluene; Heating;

DOI:10.1021/ol027450b

Reference yield: 96.0%

iodobenzene (591-50-4) + m-Anisidine (536-90-3,918666-97-4) → 3-methoxy-N-phenylaniline (101-16-6)

Guidance literature:

With potassium phosphate; tris(1,10-phenanthroline)ruthenium(II) complex; [Ni(2,2′:6′,2''-terpyridine)(pyridine)(CH₃CN)₂](PF₆)₂; In acetonitrile; for 24h; Irradiation;

DOI:10.1021/acs.organomet.8b00121

Reference yield: 95.0%

2-iodocyclohex-2-en-1-one (33948-36-6) + m-Anisidine (536-90-3,918666-97-4) → 3-methoxy-N-phenylaniline (101-16-6)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; at 75 ℃; for 1h; Inert atmosphere;

DOI:10.1002/ejoc.201201263

upstream raw materials:

3-hydroxy-N-phenylaniline

dimethyl sulfate

iodobenzene

m-Anisidine

Downstream raw materials:

N,N'-diphenyl-N,N'-bis(3-methoxyphenyl)-[1,1':4'1-terphenyl]-4,4-diamine

(E)-butyl 3-(N-(3-methoxyphenyl)-N-phenylamino)acrylate

C₃₁H₃₀FNO₄*ClH

C₃₁H₃₀FNO₄*ClH

Refernces

• 1、 Kaboudin, Babak,Abedi, Yaghoub,Yokomatsu, Tsutomu. "CuII-β-cyclodextrin complex as a nanocatalyst for the homo-and cross-coupling of arylboronic acids under ligand-and base-free conditions in air: Chemoselective cross-coupling of arylboronic acids in water". . p. 6656 - 6662. Retrieved 2011.
• 2、 Zhang, Qiang,Liu, Cunfang,Shi, Juan,Xu, Qiong,Jin, Lingxia,Zhao, Chaibin,Zhang, Tianlei. "Palladium-Catalyzed N-Arylation of Amines and Amides with Aryltrimethylgermanes". . p. 1945 - 1948. Retrieved 2016.
• 3、 Ruan, Jian-Cheng,Zhang, Tao,Wang, Shuai,Liu, Jin-Qiang,Qian, Chao,Chen, Xin-Zhi. "Improved synthesis of 2-methoxyphenothiazine". . p. 438 - 441. Retrieved 2012.
• 4、 Komori, Takashi,Satoh, Nobuhiro,Yokoshima, Satoshi,Fukuyama, Tohru. "Copper-mediated aryl amination: In situ generation of an active copper(I) species". . p. 1859 - 1862. Retrieved 2011.
• 5、 Key, Ryan J.,Vannucci, Aaron K.. "Nickel Dual Photoredox Catalysis for the Synthesis of Aryl Amines". . p. 1468 - 1472. Retrieved 2018.
• 6、 Xu, Chen,Gong, Jun-Fang,Wu, Yang-Jie. "Amination of aryl chlorides in water catalyzed by cyclopalladated ferrocenylimine complexes with commercially available monophosphinobiaryl ligands". . p. 1619 - 1623. Retrieved 2007.
• 7、 Ernst, Johannes B.,Schwermann, Christian,Yokota, Gen-Ichi,Tada, Mizuki,Muratsugu, Satoshi,Doltsinis, Nikos L.,Glorius, Frank. "Molecular Adsorbates Switch on Heterogeneous Catalysis: Induction of Reactivity by N-Heterocyclic Carbenes". . p. 9144 - 9147. Retrieved 2017.
• 8、 Urgaonkar, Sameer,Verkade, John G.. "Scope and limitations of Pd2(dba)3/P(i-BuNCH 2CH2)3N-catalyzed Buchwald-Hartwig amination reactions of aryl chlorides". . p. 9135 - 9142. Retrieved 2004.
• 9、 -. "Preparation method 3- methoxyl diphenylamine (by machine translation)". Paragraph 0008. . Retrieved 2020/04/17.