4-(Phenoxymethyl)aniline

Base Information

• Chemical Name: 4-(Phenoxymethyl)aniline
• CAS No.: 57181-90-5
• Molecular Formula: C13H13NO
• Molecular Weight: 199.252
• Hs Code.: 2922299090
• European Community (EC) Number: 839-181-3
• DSSTox Substance ID: DTXSID60507707
• Nikkaji Number: J1.566.953E
• Wikidata: Q82364084
• Mol file: 57181-90-5.mol

Synonyms:4-(phenoxymethyl)aniline;57181-90-5;4-Phenoxymethyl-aniline;Benzenamine, 4-(phenoxymethyl)-;4-phenoxymethylaniline;p-amino-benzyl phenyl ether;SCHEMBL323938;DTXSID60507707;PPRFHWKLSQQYEM-UHFFFAOYSA-N;MFCD06804490;4-(phenoxymethyl)aniline, AldrichCPR;AKOS000145392;CS-0022287;EN300-125759;F11770;Z240084658

Chemical Property of 4-(Phenoxymethyl)aniline

Chemical Property:

• PSA: 35.25000
• LogP: 3.42900
• Storage Temp.: 2-8°C
• 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-(phenoxymethyl)aniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OCC2=CC=C(C=C2)N

Technology Process of 4-(Phenoxymethyl)aniline

There total 9 articles about 4-(Phenoxymethyl)aniline 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: 95.0%

4-nitrobenzyl phenyl ether (3048-12-2) → phenyl 4-aminobenzyl ether (57181-90-5)

Guidance literature:

With hydrogen; In methanol; at 20 ℃; for 1.5h; under 760.051 Torr; chemoselective reaction;

DOI:10.1016/j.tet.2015.10.037

Reference yield: 59.0%

4-aminobenzenemethanol (623-04-1) + phenol (108-95-2,27073-41-2) → phenyl 4-aminobenzyl ether (57181-90-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2013.03.064

Reference yield:

1-methyl-4-nitrobenzene (99-99-0) → phenyl 4-aminobenzyl ether (57181-90-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / NBS, benzoylperoxide / CCl₄ / 5 h / Heating; Irradiation

2: 64 percent / 0.2 N NaOH / methanol / Ambient temperature

3: H₂ / PtO₂, 80percent / methanol / 20 h / 25 °C / 735.5 Torr

With sodium hydroxide; N-Bromosuccinimide; Perbenzoic acid; hydrogen; platinum(IV) oxide; In methanol; tetrachloromethane;

upstream raw materials:

4-nitrobenzyl phenyl ether

1-methyl-4-nitrobenzene

1-bromomethyl-4-nitro-benzene

4-nitrobenzyl chloride

Downstream raw materials:

ethyl 2-chloro-3-(4-phenoxymethylphenyl)propionate

4-aminobenzenemethanol

4-phenoxymethylphenyl isocyanate

N-(p-phenoxymethylphenyl)azetidinone

Refernces

• 1、 -. "N-(4-substituted phenyl)-2-substituted acetamide compound and is use as SIRT2 protein inhibitor". Paragraph 0160; 0162. . Retrieved 2017/08/02.
• 2、 Schmid, Kyle M.,Phillips, Scott T.. "Effect of aromaticity on the rate of azaquinone methide-mediated release of benzylic phenols". . p. 608 - 610. Retrieved 2013/07/26.