4-ethoxy-N-methylaniline

Base Information

• Chemical Name: 4-ethoxy-N-methylaniline
• CAS No.: 3154-18-5
• Molecular Formula: C9H13NO
• Molecular Weight: 151.208
• DSSTox Substance ID: DTXSID50342149
• Nikkaji Number: J1.905.797F
• Wikidata: Q82112740
• Mol file: 3154-18-5.mol

Synonyms:4-ethoxy-N-methylaniline;3154-18-5;n-methylphenetidine;Phenol, 4-methylamino, ethyl ether;N-Methyl-4-ethoxyaniline;SCHEMBL947414;benzenamine,4-ethoxy-n-methyl-;(4-Ethoxy-phenyl)-methyl-amine;DTXSID50342149;Phenol, 4-methylamino, ethyl(ether);N-(4-Ethoxyphenyl)-N-methylamine #;AKOS000252122;SB76731;BS-51686;CS-0301384;EN300-82750;E78727;Z335255846

Chemical Property of 4-ethoxy-N-methylaniline

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 151.099714038
• Heavy Atom Count: 11
• Complexity: 97.7

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC=C(C=C1)NC

Technology Process of 4-ethoxy-N-methylaniline

There total 23 articles about 4-ethoxy-N-methylaniline 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: 99.4%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-Ethoxyaniline (156-43-4) → N-methyl-p-phenetidine (3154-18-5)

Guidance literature:

With hydrogen; potassium hydroxide; silver(l) oxide; In methanol; at 125 ℃; for 4h; under 26252.6 Torr; Concentration; Autoclave;

Reference yield: 89.0%

methanol (67-56-1) + 4-Ethoxyaniline (156-43-4) → N-methyl-p-phenetidine (3154-18-5)

Guidance literature:

With potassium tert-butylate; C₃₈H₃₇ClN₂PRu⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-); In neat (no solvent); at 110 ℃; for 12h; Sealed tube; Inert atmosphere; Schlenk technique; Green chemistry;

DOI:10.1039/d1ob00362c

Reference yield:

6-ethoxy-3-(4-ethoxy-phenyl)-3,4-dihydro-quinazoline (796-99-6) + acetic acid (64-19-7,77671-22-8) → N-methyl-p-phenetidine (3154-18-5) + 4-Ethoxyaniline (156-43-4)

Guidance literature:

upstream raw materials:

formaldehyd

4-ethoxyaniline hydrochloride

N-methyl-p-aminophenol

Diethyl phthalate

Downstream raw materials:

1,3-dimethyl-5-hydroxyoxindole

2-bromo-butyric acid-(N-methyl-p-phenetidide)

N-(4-ethoxy-phenyl)-N-methyl-thiourea

1-methyl-5-hydroxy-2-indolinone

Refernces

• 1、 Huang, Ming,Li, Yinwu,Lan, Xiao-Bing,Liu, Jiahao,Zhao, Cunyuan,Liu, Yan,Ke, Zhuofeng. "Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols". supporting information. p. 3451 - 3461. Retrieved 2021/05/03.
• 2、 Huang, Ming,Li, Yukui,Li, Yinwu,Liu, Jiahao,Shu, Siwei,Liu, Yan,Ke, Zhuofeng. "Room temperature N-heterocyclic carbene manganese catalyzed selective N-alkylation of anilines with alcohols". supporting information. p. 6213 - 6216. Retrieved 2019/06/07.