Benzoic acid nitrogen mustard

Base Information

• Chemical Name: Benzoic acid nitrogen mustard
• CAS No.: 1141-37-3
• Molecular Formula: C11H13 Cl2 N O2
• Molecular Weight: 262.136
• Hs Code.: 2922499990
• NSC Number: 26276
• UNII: KD3AZX3R33
• DSSTox Substance ID: DTXSID40150654
• Nikkaji Number: J41.217A
• Wikidata: Q83016818
• ChEMBL ID: CHEMBL12293
• Mol file: 1141-37-3.mol

Synonyms:4-N-bis(2-chloroethyl)aminobenzoic acid

Chemical Property of Benzoic acid nitrogen mustard

Chemical Property:

• Vapor Pressure: 4.9E-08mmHg at 25°C
• Refractive Index: 1.6070 (estimate)
• Boiling Point: 426.6°Cat760mmHg
• Flash Point: 211.8°C
• PSA: 40.54000
• Density: 1.339g/cm³
• LogP: 2.66880
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 261.0323340
• Heavy Atom Count: 16
• Complexity: 212

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)O)N(CCCl)CCCl

Technology Process of Benzoic acid nitrogen mustard

There total 19 articles about Benzoic acid nitrogen mustard 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%

tert-butyl 4-[bis-(2-chloroethyl)amino]benzoate → 4-{bis(2-chloroethyl)amino}benzoic acid (1141-37-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.ejmech.2013.10.080

Reference yield: 89.0%

p-N,N-bis(2-chloroethyl)aminophenol acetate → 4-{bis(2-chloroethyl)amino}benzoic acid (1141-37-3)

Guidance literature:

With hydrogenchloride; In water; for 2h; Reflux;

Reference yield: 50.0%

4-(bis(2-chloroethyl)amino)benzaldehyde (1208-03-3) → 4-{bis(2-chloroethyl)amino}benzoic acid (1141-37-3)

Guidance literature:

With potassium permanganate; In pyridine; water; at 20 ℃; for 20h;

DOI:10.3184/174751912X13362343090928

upstream raw materials:

4-[bis-(2-chloro-ethyl)-amino]-benzoic acid ethyl ester

4-(bis(2-chloroethyl)amino)benzaldehyde

4-benzoyl-L-glutamic acid

di-tert-butyl 4-benzoyl-L-glutamate

Downstream raw materials:

4-(2-chloroethyl)-3-[[5-(4-bis-(2-chloroethyl)amino)benzamido]indole-2-carboxamido]phenol

4-[N,N-bis(2-chloroethyl)amino]benzoyl chloride

4-(bis(2-chloroethyl)amino)-N-(3-morpholinopropyl)benzamide

4-(bis(2-chloroethyl)amino)-N-(2-fluorophenyl)benzamide

Refernces

Synthesis, biological evaluation and molecular docking studies of amide-coupled benzoic nitrogen mustard derivatives as potential antitumor agents

10.1016/j.bmc.2009.11.037

The study reports the synthesis, biological evaluation, and molecular docking studies of a series of amide-coupled benzoic nitrogen mustard derivatives as potential antitumor agents targeting EGFR and HER-2 kinases. The researchers synthesized these derivatives, which were evaluated for their ability to inhibit the autophosphorylation of EGFR and HER-2 kinases using a solid-phase ELISA assay. Compounds 5b and 5t exhibited the most potent inhibitory activity, comparable to the positive control erlotinib. Molecular docking simulations were performed to explore the binding modes of these compounds at the EGFR active site. The antiproliferative activity of the synthesized compounds was also evaluated on the MCF-7 human tumor cell line, with compounds 5b and 5t showing significant inhibitory activity in tumor growth inhibition. Overall, the study suggests that these benzoic nitrogen mustard derivatives, particularly compounds 5b and 5t, have potential as antitumor agents due to their potent inhibitory activity against EGFR and HER-2 kinases.