TRIS-(2-CHLOROETHYL)-AMINE Chemical Properties

Melting point:

-4°

Boiling point:

bp15 144°

Density 

d425 1.2347

refractive index 

nD25 1.4925

storage temp. 

-20°C

pka

5.05±0.50(Predicted)

form 

HN-3 may smell like bitter almond.

EPA Substance Registry System

Nitrogen mustard (HN-3) (555-77-1)

Safety Information

RIDADR 

2810

HazardClass 

6.1(a)

PackingGroup 

I

Hazardous Substances Data

555-77-1(Hazardous Substances Data)

Toxicity

LD50 oral in rat: 5mg/kg

TRIS-(2-CHLOROETHYL)-AMINE Usage And Synthesis

Description

Nitrogen mustards are very potential chemical substances of yesteryears and produced during the 1920s and 1930s as chemical warfare weapons. They are vesicants (or blister agents) similar to the sulphur mustards. They smell fishy, musty, soapy, or fruity and are either in the form of an oily textured liquid or a vapour (the gaseous form of a liquid) or a solid. It is in liquid form at normal room temperature (70 F) with a clear, pale amber, or yellow colour. HN-1, HN-2, and HN-3 are the military designations of nitrogen mustard (for more data, refer to Muatars gas). Nitrogen mustards (HN-1, HN-2, HN-3) are colourless to yellow, oily liquids that evaporate very slowly. HN-1 has a faint fishy or musty odour. HN-2 has a soapy odour at low concentrations and a fruity odour at higher concentrations. HN-3 may smell like butter almond. Use of nitrogen mustards is very much restricted other than for chemical warfare. In fact, presently, its use has no records. HN-1 has been used to remove warts in the past, and HN-2 has been used sparingly in chemotherapy.

Chemical Properties

HN-3, a nitrogen mustard blister agent (vesicants, is a colorless to pale yellow liquid. Pure material is odorless; otherwise, it has a faint fish-or soap-like odor.

General Description

Liquid with faint odor of fish and soap, no odor when pure. Used as a delayed-action casualty military agent.

Air & Water Reactions

Acts as a strong base in water.

Reactivity Profile

When dissolved in water, TRIS-(2-CHLOROETHYL)-AMINE is a strong base; reacts violently with strong oxidants and acids ; attacks copper and copper compounds. [Handling Chemicals Safely 1980. p. 123]; reacts with hypochlorites to give N-chloroamines, some of which are explosives when isolated [Bretherick 1979. p. 108].

Health Hazard

Most toxic of the nitrogen mustards. The median lethal dose for inhalation is 1,500 mg-min/m3; for skin absorption (masked personnel) is 10,000 mg-min/m3. The medium incapacitating dose for eye injury is 200 mg-min/m3; for skin absorption is 2,500 mg-min/m3.

Fire Hazard

When heated to decomposition, TRIS-(2-CHLOROETHYL)-AMINE emits chloride and nitrogen oxides. No action on metals or other materials if material is kept dry. Avoid decomposing heat.

Potential Exposure

Trichlorotriethylamine is a (slowacting) vesicant but has never been used in military conflict. Is used as an antineoplastic agent. Has been tested as a fixing agent in textile dyes.

Carcinogenicity

Tris(β-chloroethyl)amine was tested for carcinogenic potential in mice and rats given the material by subcutaneous injection. The study in mice was considered inadequate for evaluation by the IARC. However, in rats, this material induced a high incidence of sarcomas (mostly spindle-cell type) in animals of each sex at the site of injection, as well as a few intestinal adenocarcinomas; neither tumor type was seen in controls. Intravenous, intraperitoneal, and subcutaneous injection to mice and rats produced tumors in 15–20% of treated animals. The tumors included fibrosarcomas, lymphosarcomas, and adenocarcinomas, and administration of a single dose was as effective in inducing tumors as multiple injections.
IARC considered the preceding data “sufficient evidence of carcinogenicity in experimental animals.” Although no human carcinogenicity data were available, the IARC classified tris(β-chloroethyl)amine in Group 2B (the agent is possibly carcinogenic to humans). This classification was based on these animal studies, its mutagenic potential, and analogy to other nitrogen mustards.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. Military driver of HN-3 shall be given full and complete information regarding shipment and conditions in case of emergency. AR 50-6 deals specifically with the shipment of chemical agents. Shipments of agent will be escorted in accordance with AR 740-32.

Incompatibilities

HN-3 is not stable; it undergoes slow but steady polymerization. Avoid contamination with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, bleaches and pool chemicalsetc); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Unstable in the presence of light and heat and forms dimers at temperatures above 50℃. HN-3 decomposes before its boiling point is reached or condenses under all conditions; the reactions involved could generate enough heat to cause an explosion. Polymerizes slowly, so munitions would be effective for several years. Heated to decomposition emits hydrogen chloride and nitrogen oxide. Note: Chlorinating agents destroy nitrogen mustards. Dry chlorinated lime and chloramines with a high content of active chlorine vigorously chlorinate nitrogen mustards to the carbon chain giving low toxicity products. In the presence of water this interaction proceeds less actively. They are rapidly oxidized by peracids in aqueous solution at weakly alkaline pH. In acid solution the oxidation is much slower.

TRIS-(2-CHLOROETHYL)-AMINE(555-77-1)Related Product Information

• TRIS(2-CHLOROETHYL)AMINE HYDROCHLORIDE
• bis(2-chloroethyl)ethylamine
• Chlormethine
• 2-Diethylaminoethylchloride hydrochloride
• Nornitrogen mustard
• Mechlorethamine hydrochloride
• Bis(2-chloroethyl)amine hydrochloride
• TRIS-(2-CHLOROETHYL)-AMINE