4-Phenoxyaniline

Base Information

• Chemical Name: 4-Phenoxyaniline
• CAS No.: 139-59-3
• Molecular Formula: C12H11NO
• Molecular Weight: 185.225
• Hs Code.: 29222990
• European Community (EC) Number: 205-367-2
• NSC Number: 61131,57084,4629
• UNII: 44P7PAW368
• DSSTox Substance ID: DTXSID8059687
• Nikkaji Number: J33.852D
• Wikidata: Q72500955
• ChEMBL ID: CHEMBL249550
• Mol file: 139-59-3.mol

Synonyms:4-aminodiphenyl ether;4-aminodiphenyl ether hydrochloride

Chemical Property of 4-Phenoxyaniline

Chemical Property:

• Appearance/Colour: brown to green-brown crystalline flakes or powder
• Melting Point: 82-84 °C(lit.)
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 320 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 155.8 °C
• PSA: 35.25000
• Density: 1.141 g/cm³
• LogP: 3.64230
• Water Solubility.: < 1 g/L (20℃)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 185.084063974
• Heavy Atom Count: 14
• Complexity: 158

Purity/Quality:

98%, ^*data from raw suppliers

4-Phenoxyaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43-68-50/53
• Safety Statements: 26-36/37/39-61-45-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2=CC=C(C=C2)N
• Chemical Composition and Structure: 4-Phenoxyaniline is an organic compound consisting of a phenyl ring attached to an amino group (-NH2) and a phenoxy group (-O-Ph).
• Uses: Dye Intermediate:; Commonly used as a dye intermediate in the synthesis of various organic dyes.; ; Neuroprotective Agent:; N-acyl-substituted derivatives of 4-phenoxyaniline have shown significant protection against glutamate- and Bid-induced toxicity in cultured neurons, indicating potential neuroprotective properties.^[1]; ; Intermediate in Drug Synthesis:; Incorporated as a substituent in the synthesis of pyrrolopyridazine MEK inhibitors, which are used in pharmaceutical research and drug development.^[2]; ; Component in Proton Exchange Membranes:; Used in the synthesis of sulfonated polyimides for proton-exchange membranes, which have applications in fuel cells and other electrochemical devices.^[3]; ; Component in Electrically Bistable Memory Devices:; Utilized in the synthesis of poly(triphenylamines) for constructing resistive switching devices with applications in non-volatile memory devices.^[4]
• References: [1] N-Acyl Derivatives of 4-Phenoxyaniline as Neuroprotective Agents; DOI 10.1002/cmdc.201402195; [2] Pyrrolopyridazine MEK inhibitors; DOI 10.1016/j.bmcl.2005.10.052; [3] Novel sulfonated polyimides proton-exchange membranes via a facile polyacylation approach of imide monomers; DOI 10.1016/j.memsci.2013.12.062; [4] Electrically bistable and non-volatile memory devices based on p-toluenesulfonic-doped poly(triphenylamine); DOI 10.1039/C6RA01410K

Technology Process of 4-Phenoxyaniline

There total 43 articles about 4-Phenoxyaniline 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%

4-nitrophenyl phenyl ether (620-88-2) → 4-phenoxyanilin (139-59-3)

Guidance literature:

With iron; ammonium chloride; In ethanol; water; at 60 ℃; for 3h;

DOI:10.1021/acs.jmedchem.0c00870

Reference yield: 98.0%

iodobenzene (591-50-4) + 4-amino-phenol (123-30-8) → 4-phenoxyanilin (139-59-3)

Guidance literature:

With copper(II) glycinate monohydrate; potassium hydroxide; In dimethyl sulfoxide; at 80 ℃; for 8h;

DOI:10.1016/j.tetlet.2012.06.071

Reference yield: 95.0%

4-bromo-aniline (106-40-1) + phenol (108-95-2,27073-41-2) → 4-phenoxyanilin (139-59-3)

Guidance literature:

With sodium hydroxide; In neat (no solvent); at 90 ℃; for 6h; Green chemistry;

DOI:10.1007/s10562-019-03070-5

upstream raw materials:

4-nitrophenyl phenyl ether

p-phenoxyacetanilide

2-bromoaniline

phenol

Downstream raw materials:

4-phenoxy-N,N-bis-(2-hydroxy-ethyl)-aniline

nicotinic acid-(4-phenoxy-anilide)

(4-phenoxy-phenyl)-carbamic acid ethyl ester

1,5-bis-(4-phenoxy-anilino)-anthraquinone

Refernces

• 1、 Wienhoefer, Gerrit,Baseda-Krueger, Mario,Ziebart, Carolin,Westerhaus, Felix A.,Baumann, Wolfgang,Jackstell, Ralf,Junge, Kathrin,Beller, Matthias. "Hydrogenation of nitroarenes using defined iron-phosphine catalysts". . p. 9089 - 9091. Retrieved 2013.
• 2、 Yoo, Byung Woo,Kim, Duckil,Kim, Hyung Min,Kang, Sung Ho. "Efficient and selective reduction of aromatic nitro compounds to aromatic amines by NbCl5/indium system". . p. 2851 - 2852. Retrieved 2012.
• 3、 Luo, Yunting,Wu, Jeff Xin,Ren, Rex X.. "Ullmann diaryl ether synthesis in ionic liquids". . p. 1734 - 1736. Retrieved 2003.
• 4、 Fujii, Shinya,Kikuchi, Eriko,Suzuyama, Honoka,Watanabe, Yuko,Ishigami-Yuasa, Mari,Masuno, Hiroyuki,Mori, Takayasu,Isobe, Kiyoshi,Uchida, Shinichi,Kagechika, Hiroyuki. "Structural Development of Salicylanilide-Based SPAK Inhibitors as Candidate Antihypertensive Agents". supporting information. p. 2817 - 2822. Retrieved 2021/07/12.
• 5、 Lategahn, Jonas,Hardick, Julia,Grabe, Tobias,Niggenaber, Janina,Jeyakumar, Kirujan,Keul, Marina,Tumbrink, Hannah L.,Becker, Christian,Hodson, Luke,Kirschner, Tonia,Kl?vekorn, Philip,Ketzer, Julia,Baumann, Matthias,Terheyden, Susanne,Unger, Anke,Weisner, J?rn,Müller, Matthias P.,Van Otterlo, Willem A. L.,Bauer, Sebastian,Rauh, Daniel. "Targeting Her2-insYVMA with Covalent Inhibitors - A Focused Compound Screening and Structure-Based Design Approach". . p. 11725 - 11755. Retrieved 2020/11/26.