Benzoic acid, 4-[bis(chloromethyl)amino]-, methyl ester

Base Information

• Chemical Name: Benzoic acid, 4-[bis(chloromethyl)amino]-, methyl ester
• CAS No.: 922499-00-1
• Molecular Formula: C₁₀H₁₁Cl₂NO₂
• Molecular Weight: 248.109
• Mol file: 922499-00-1.mol

Synonyms:

Chemical Property of Benzoic acid, 4-[bis(chloromethyl)amino]-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzoic acid, 4-[bis(chloromethyl)amino]-, methyl ester

There total 2 articles about Benzoic acid, 4-[bis(chloromethyl)amino]-, methyl ester 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:

4-(bis-hydroxymethyl-amino)-benzoic acid methyl ester → N,N-(ClCH2)2NC6H4CO2Me-p (922499-00-1)

Guidance literature:

With thionyl chloride; In dichloromethane; for 2h;

DOI:10.1016/j.jorganchem.2006.06.044

Reference yield:

4-methoxycarbonyl aniline (619-45-4) → N,N-(ClCH2)2NC6H4CO2Me-p (922499-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 5 h / 20 °C

2: 4.46 g / SOCl₂ / CH₂Cl₂ / 2 h

With thionyl chloride; In dichloromethane;

DOI:10.1016/j.jorganchem.2006.06.044

Reference yield: 75.0%

N,N-(ClCH2)2NC6H4CO2Me-p (922499-00-1) + Fe2(μ-S)2(CO)6 → [(μ-SCH2)2N(C6H4CO2Me-p)]Fe2(CO)6 (922499-04-5)

Guidance literature:

With (C₂H₅)3BHLi; In tetrahydrofuran; (N2); using Schlenk techniques; cooling of soln. of S2Fe2(CO)6 in THF to-78°C; addn. of soln. of Et3BHLi in THF; addn. of (ClCH2)2NC6H4C O2Me; warming to room temp., stirring at this temp. for 8 h; filtration, evapn. of filtrate to dryness; TLC; using CH2Cl2/petroleum ether (1:5) as eluant; elem. anal.;

upstream raw materials:

4-methoxycarbonyl aniline

Downstream raw materials:

[(μ-SCH2)2N(C6H4CO2Me-p)]Fe2(CO)6

Refernces