Diethyl 4-N,N-dimethylaminobenzylphosphonate

Base Information

• Chemical Name: Diethyl 4-N,N-dimethylaminobenzylphosphonate
• CAS No.: 32264-24-7
• Molecular Formula: C13H22NO3P
• Molecular Weight: 271.296
• Mol file: 32264-24-7.mol

Synonyms:

Chemical Property of Diethyl 4-N,N-dimethylaminobenzylphosphonate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Diethyl 4-N,N-dimethylaminobenzylphosphonate

There total 5 articles about Diethyl 4-N,N-dimethylaminobenzylphosphonate 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: 92.0%

p-(dimethylamino)benzaldehyde tosylhydrazone (18708-16-2) + phosphonic acid diethyl ester (762-04-9) → diethyl 4-N,N-dimethylaminobenzylphosphonate (32264-24-7)

Guidance literature:

With copper(l) iodide; caesium carbonate; In 1,2-dimethoxyethane; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.1002/adsc.201200295

Reference yield: 50.0%

C5H12IO3PZn (1137728-03-0) + 4-Iodo-N,N-dimethylaniline (698-70-4) → diethyl 4-N,N-dimethylaminobenzylphosphonate (32264-24-7)

Guidance literature:

C₅H₁₂IO₃PZn; With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,1'-bis(diphenylphosphino)ferrocene; In tetrahydrofuran; for 0.0833333h; Inert atmosphere;

4-Iodo-N,N-dimethylaniline; In tetrahydrofuran; at 60 ℃; for 10h; Inert atmosphere;

DOI:10.1021/jo900142b

Reference yield: 25.0%

N,N-dimethyl-4-hydroxymethylaniline (1703-46-4) + triethyl phosphite (122-52-1) → diethyl 4-N,N-dimethylaminobenzylphosphonate (32264-24-7)

Guidance literature:

N,N-dimethyl-4-hydroxymethylaniline; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h;

triethyl phosphite; With sodium iodide; at 110 ℃; for 2.5h; Further stages.;

DOI:10.1002/ejic.200601214

upstream raw materials:

N,N-dimethyl-4-hydroxymethylaniline

triethyl phosphite

C₅H₁₂IO₃PZn

4-Iodo-N,N-dimethylaniline

Downstream raw materials:

N,N-dimethyl-4-[(E)-2-(6-chloropyridin-3-yl)vinyl]aniline

4-[(E)-2-(6-fluoropyridin-3-yl)vinyl]-N,N-dimethylaniline

4-(N,N-dimethylamino)stilbene

4-dimethylamino-4'-chloride-stilbene

Refernces

• 1、 Miao, Wenjun,Gao, Yuzhen,Li, Xueqin,Gao, Yuxing,Tang, Guo,Zhao, Yufen. "Copper-catalyzed synthesis of alkylphosphonates from H-phosphonates and N-tosylhydrazones". . p. 2659 - 2664. Retrieved 2013/01/15.