Bis(2-chloroethyl)ethylamine

Base Information

• Chemical Name: Bis(2-chloroethyl)ethylamine
• CAS No.: 538-07-8
• Molecular Formula: C6H13 Cl2 N
• Molecular Weight: 170.082
• Hs Code.: 2921193000
• ICSC Number: 1655
• UN Number: 2810
• UNII: B75ZZA7WIG
• DSSTox Substance ID: DTXSID0060220
• Nikkaji Number: J6.367C
• Wikipedia: HN1_(nitrogen_mustard)
• Wikidata: Q5635296
• Mol file: 538-07-8.mol

Synonyms:bis(2-chloroethyl)ethylamine;HN-1 cpd

Chemical Property of Bis(2-chloroethyl)ethylamine

Chemical Property:

• Vapor Pressure: 7.63mmHg at 25°C
• Melting Point: -33.9°C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 135.7°C at 760 mmHg
• PKA: 6.48±0.50(Predicted)
• Flash Point: 35.9°C
• PSA: 3.24000
• Density: 1.079g/cm³
• LogP: 1.78590
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 169.0425048
• Heavy Atom Count: 9
• Complexity: 53

Purity/Quality:

99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Chemical Weapons
• Canonical SMILES: CCN(CCCl)CCCl
• Inhalation Risk: A harmful contamination of the air will be reached quickly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: Blistering agent. Lachrymation. The substance is severely irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system and bone marrow. Inhalation may cause lung oedema. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the bone marrow and central nervous system. This substance is probably carcinogenic to humans. May cause heritable genetic damage to human germ cells.
• Uses: Although nitrogen mustards could be used in chemical warfare, there are presently no records of such use. HN-1 has been used to remove warts in the past, Nitrogen mustards are among the blister agents/vesicants used in chemical warfare. HN-1 was originally designed to remove warts and later identified as a potential chemical warfare agent. HN-2 was designed as a military agent, but later used in cancer chemotherapy. HN-3 was developed as a military chemical warfare agent. Nitrogen mustards have also found therapeutic applications in cancer treatment, and there are several pharmaceutical derivatives that were developed as cancer therapeutic agents.

Technology Process of Bis(2-chloroethyl)ethylamine

There total 2 articles about Bis(2-chloroethyl)ethylamine 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: 76.0%

ethyldiethanolamine (139-87-7) → bis(2-chloroethyl)(ethyl)amine (538-07-8)

Guidance literature:

ethyldiethanolamine; With thionyl chloride; In dichloromethane; at 0 - 20 ℃; for 20h;

With sodium hydrogencarbonate; In dichloromethane; water; pH=7;

Reference yield:

N,N-bis-(2-chloro-ethyl)-acetamide (19945-22-3) → bis(2-chloroethyl)(ethyl)amine (538-07-8)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; Ambient temperature;

Reference yield: 86.0%

bis(2-chloroethyl)(ethyl)amine (538-07-8) + C22H22BrNO → C50H55Br2N3O2

Guidance literature:

C₂₂H₂₂BrNO; With sodium hydride; In 1,4-dioxane; at 20 ℃; for 0.5h;

bis(2-chloroethyl)(ethyl)amine; In 1,4-dioxane; at 110 ℃; for 1h;

DOI:10.1016/j.dyepig.2020.108985

upstream raw materials:

ethyldiethanolamine

N,N-bis-(2-chloro-ethyl)-acetamide

Downstream raw materials:

ethyl-bis-(2-thiocyanato-ethyl)-amine

ethylcholine mustard

ethyl-bis-(2-chloro-ethyl)-amine oxide

1-ethyl-1-(2-chloro-ethyl)-aziridinium; chloride

Refernces

• 1、 -. "NOVEL BENZENESULFONAMIDE COMPOUNDS, METHOD FOR SYNTHESIZING SAME, AND USE THEREOF IN MEDICINE AS WELL AS IN COSMETICS". Paragraph 0302. . Retrieved 2014/09/30.
• 2、 -. "N- [2-HYDROXYCARBAMOYL-2- (PIPERAZINYL) ETHYL] BENZAMIDE COMPOUNDS, THEIR PREPARATION AND THEIR USE AS TACE INHIBITORS". Page/Page column 67. . Retrieved 2011/04/19.