Bis(2-chloroethyl)amine

Base Information

• Chemical Name: Bis(2-chloroethyl)amine
• CAS No.: 334-22-5
• Molecular Formula: C4H9 Cl2 N
• Molecular Weight: 142.028
• Hs Code.: 2921199090
• UNII: IHV3I38UXH
• DSSTox Substance ID: DTXSID60187028
• Nikkaji Number: J126.297A
• Wikidata: Q27117201
• Metabolomics Workbench ID: 55634
• ChEMBL ID: CHEMBL913
• Mol file: 334-22-5.mol

Synonyms:nor-N-mustard;nor-nitrogen mustard;nornitrogen mustard;nornitrogen mustard, hydrobromide;nornitrogen mustard, hydrochloride;nornitrogen mustard, hydroiodide

Chemical Property of Bis(2-chloroethyl)amine

Chemical Property:

• Refractive Index: 1.5500 (estimate)
• Boiling Point: 204.2°Cat760mmHg
• PKA: 7.02±0.19(Predicted)
• Flash Point: 77.3°C
• PSA: 12.03000
• Density: 1.125g/cm³
• LogP: 1.44450
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 141.0112047
• Heavy Atom Count: 7
• Complexity: 28.9

Purity/Quality:

98% ^*data from raw suppliers

BIS(2-CHLOROETHYL)AMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: Poison by intraperitoneal, subcutaneous, and intravenous routes. Experimental reproductive eff"> x and Cl−." target="_blank">Poison by intraperitoneal, subcutaneous, and intravenous routes. Experimental reproductive eff

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCl)NCCCl

Technology Process of Bis(2-chloroethyl)amine

There total 11 articles about Bis(2-chloroethyl)amine 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: 82.0%

2,2'-iminobis[ethanol] (111-42-2) → N,N-bis(chloro-2-ethyl)amine (334-22-5)

Guidance literature:

With thionyl chloride; In chloroform; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2006.11.016

Reference yield: 70.0%

bis-(2-chloroethyl)amine hydrochloride (821-48-7) → N,N-bis(chloro-2-ethyl)amine (334-22-5)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; at 20 ℃; for 6h;

DOI:10.1007/s11164-018-3411-3

Reference yield:

phosgene (75-44-5) + bis(2-chloroethylamine) hydrochloride + methyl cholate (1448-36-8) → N,N-bis(chloro-2-ethyl)amine (334-22-5)

Guidance literature:

With potassium hydroxide; triethylamine; In dichloromethane; water; benzene;

upstream raw materials:

2,2'-iminobis[ethanol]

bis-(2-chloroethyl)amine hydrochloride

tetrachloromethane

nitrogen mustard

Downstream raw materials:

N,N-bis-(2-chloroethyl)carbamoyl chloride

trifluoro-acetic acid-[bis-(2-chloro-ethyl)-amide]

1,4-bis-(2-chloro-ethyl)-piperazine

bis-(2-chloro-ethyl)-carbamonitrile

Refernces

Intramolecular Condensation Reactions of 1,1,3,3-Tetrakis(2-chloroethyl)urea

10.1021/jo00828a075

The study investigates the intramolecular condensation reactions of 1,1,3,3-tetrakis(2-chloroethyl)urea (Ia). The researchers prepared Ia by reacting bis(2-chloroethyl)carbamoyl chloride with bis(2-chloroethyl)amine in refluxing benzene. Upon distillation, Ia unexpectedly transformed into 1,3-bis(2-chloroethyl)-2-imidazolidinone (IIa), indicating a rearrangement from a tetrasubstituted urea to an imidazolidinone structure. This transformation was further explored through alternative syntheses and reactions with other reagents. For instance, bis(2-chloroethyl)carbamoyl chloride was reacted with diethylamine to produce 1-(2-chloroethyl)-3-ethyl-2-imidazolidinone (IIc), and with pyrrolidine to yield 1-(4-chlorobutyl)-3-(2-chloroethyl)-2-imidazolidinone (IId). Additionally, the study examined the behavior of Ia in aqueous solution, where it underwent hydrolysis to form bis(2-[(2-chloroethyl)amino]ethyl) carbonate (V). The study provides insights into the reactivity and transformation pathways of these chloroethyl-containing ureas and imidazolidinones under different conditions.