N,N-bis(2-chloroethyl)-4-nitroaniline

Base Information

• Chemical Name: N,N-bis(2-chloroethyl)-4-nitroaniline
• CAS No.: 55743-71-0
• Molecular Formula: C10H12 Cl2 N2 O2
• Molecular Weight: 263.123
• NSC Number: 42074
• Nikkaji Number: J271.540F
• ChEMBL ID: CHEMBL19995
• Mol file: 55743-71-0.mol

Synonyms:N,N-Bis(2-chloroethyl)-4-nitroaniline;N,N-Bis(2-chloroethyl)-p-nitroaniline; NSC 42074; SN 23163

Chemical Property of N,N-bis(2-chloroethyl)-4-nitroaniline

Chemical Property:

• Vapor Pressure: 1.07E-06mmHg at 25°C
• Boiling Point: 402.7°C at 760 mmHg
• Flash Point: 197.4°C
• Density: 1.348g/cm³
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 262.0275830
• Heavy Atom Count: 16
• Complexity: 209

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1N(CCCl)CCCl)[N+](=O)[O-]

Technology Process of N,N-bis(2-chloroethyl)-4-nitroaniline

There total 5 articles about N,N-bis(2-chloroethyl)-4-nitroaniline 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%

N,N-bis(2-hydroxyethyl)-4-nitroaniline (18226-17-0) → bis(2-chloroethyl)(4-nitrophenyl)amine (55743-71-0)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; for 3h; Time; Reflux;

Reference yield: 90.3%

N,N-bis<2-<(methylsulfonyl)oxy>ethyl>-4-nitroaniline (23721-18-8) → bis(2-chloroethyl)(4-nitrophenyl)amine (55743-71-0)

Guidance literature:

With lithium chloride; In N,N-dimethyl-formamide; at 110 ℃; for 0.166667h;

Reference yield:

4-chlorobenzonitrile (100-00-5) → bis(2-chloroethyl)(4-nitrophenyl)amine (55743-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 34 percent / 6 h / 115 - 120 °C

2: 80 percent / Et₃N / ethyl acetate / 0.08 h

3: 80 percent / NaCl / dimethylformamide / 0.17 h / 160 °C

With triethylamine; sodium chloride; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00163a019

upstream raw materials:

N,N-bis<2-<(methylsulfonyl)oxy>ethyl>-4-nitroaniline

N,N-bis(2-hydroxyethyl)-4-nitroaniline

4-Fluoronitrobenzene

4-nitro-aniline

Downstream raw materials:

C₃₀H₃₄N₄O₄S₅

C₂₆H₂₆Cl₂N₄O₄S₂

C₂₂H₂₄N₄O₂S₂

TH-1104

Refernces

• 1、 -. "Hydrogen peroxide-responsive nitrogen mustard anti-tumor pro-drug and preparation method thereof". Paragraph 0112-0115. . Retrieved 2019/10/17.
• 2、 -. "Pyrazolo [1, 5 - a] pyrimidine nitrogen mustard derivative and its preparation method and tumor therapeutic use". Paragraph 0106; 0107; 0108. . Retrieved 2017/08/02.