555-77-1

Basic information

• Product Name: TRIS-(2-CHLOROETHYL)-AMINE
• Synonyms: 2,2',2''-Trichlorotriethylamine;2,2',2-Trichlorotriethylamine;2,2’,2"-trichloro-triethylamin;2,2’,2"-trichlorotriethylamine;2,2’,2’’-trichloro-triethylamin;2,2’,2’’-trichlorotriethylamine;2-chloro-n,n-bis(2-chloroethyl)-ethanamin;2-Chloro-N,N-bis(2-chloroethyl)ethanamine
• CAS NO: 555-77-1
• Molecular Formula: C₆H₁₂Cl₃N
• Molecular Weight: 204.53
• EINECS: 212-442-3
• Mol File: 555-77-1.mol

Chemical Properties

• Melting Point: -4°
• Boiling Point: bp15 144°
• Flash Point: 48.3°C
• Appearance: /
• Density: d425 1.2347
• Vapor Pressure: 2.92mmHg at 25°C
• Refractive Index: nD25 1.4925
• Storage Temp.: -20°C
• PKA: 5.05±0.50(Predicted)
• CAS DataBase Reference: TRIS-(2-CHLOROETHYL)-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS-(2-CHLOROETHYL)-AMINE(555-77-1)
• EPA Substance Registry System: TRIS-(2-CHLOROETHYL)-AMINE(555-77-1)

Safety Data

• RIDADR: 2810
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 555-77-1(Hazardous Substances Data)

Usage

Uses

Used in Military Applications:
TRIS-(2-CHLOROETHYL)-AMINE is used as a delayed-action casualty agent for military purposes. It serves as a chemical weapon that can cause severe injuries and casualties when used in warfare.
Used in Chemical Research:
TRIS-(2-CHLOROETHYL)-AMINE can also be used as a subject of study in chemical research, particularly in the field of chemical warfare agents and their effects on human health and the environment. This research can contribute to the development of countermeasures and protective measures against such agents.

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.

InChI:InChI=1/C6H12Cl3N.ClH/c7-1-4-10(5-2-8)6-3-9;/h1-6H2;1H

Upstream product

• 102-71-6 triethanolamine 
• 637-39-8 triethanolamine hydrochloride 
• 50711-75-6 chloro-acetic acid-[bis-(2-chloro-ethyl)-amide] 
• 817-09-4 tris-(2-chloroethyl)amine hydrochloride 

Downstream Products

• 27807-62-1 bis-(2-chloro-ethyl)-(2-methoxy-ethyl)-amine; hydrochloride 
• 104-19-8 N-methyl-N'-(2-dimethylaminoethyl)piperazine 
• 33527-91-2 tris[2-(dimethylamino)ethyl]amine 
• 72521-03-0 1-(2-anilinoethyl)-4-phenylpiperazine 
• 114099-16-0 (2-benzyloxy-ethyl)-bis-(2-chloro-ethyl)-amine; hydrochloride 
• 100951-30-2 N-acetyl-anthranilic acid-{2-[bis-(2-chloro-ethyl)-amino]-ethyl ester} 
• 113186-77-9 bis-(2-chloro-ethyl)-(2-cyclohexyloxy-ethyl)-amine; hydrochloride 
• 27807-61-0 (2-butoxy-ethyl)-bis-(2-chloro-ethyl)-amine; hydrochloride 
• 84928-99-4 2-azido-N,N-bis(2-azidoethyl)ethanamine 
• 26458-78-6 4-cyanoquinuclidine 
• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 622-40-2 2-(morpholin-4-yl)ethanol 
• 102-71-6 triethanolamine 
• 4669-21-0 2,2'-[(2-chloroethyl)amino]diethanol 

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