545-55-1

Basic information

• Product Name: TEPA
• Synonyms: 1,1’,1"-phosphinylidynetris-aziridin;1,1’,1’’-phosphinylidynetris-aziridin;1,1’,1’’-phosphinylidynetrisaziridine;1-aziridinylphosphineoxide(tris);a6366;aphoxide;cbc906288;ent24915
• CAS NO: 545-55-1
• Molecular Formula: C₆H₁₂N₃OP
• Molecular Weight: 173.15
• EINECS: 208-892-5
• Product Categories: Heterocycles;Phosphorylating and Phosphitylating Agents
• Mol File: 545-55-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 41℃
• Boiling Point: 299℃
• Flash Point: 135℃
• Appearance: /solid
• Density: 1.47
• Storage Temp.: -20°C
• PKA: 2.74±0.20(Predicted)
• Stability: Stable.
• CAS DataBase Reference: TEPA(CAS DataBase Reference)
• NIST Chemistry Reference: TEPA(545-55-1)
• EPA Substance Registry System: TEPA(545-55-1)

Safety Data

• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 545-55-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless crystals. Soluble in water, alcohol, and ether. Combustible.

Uses

Different sources of media describe the Uses of 545-55-1 differently. You can refer to the following data:
1. Used as insect chemosterilant; in dyeing. Antineoplastic.
2. Insect chemosterilant; in dyeing, creaseproofing and flameproofing textiles; stabilizer for polymers; in photographic emulsion hardening.

General Description

An aqueous solution of a colorless crystalline solid. Toxic by skin absorption, ingestion or inhalation. Produces toxic oxides of nitrogen during combustion. Used as a pesticide.

Reactivity Profile

TRIS-(1-AZIRIDINYL) PHOSPHINE OXIDE may react with aqueous solutions of acids or strong bases. Undergoes slow decomposition in water, not considered hazardous. Polymerizes violently at about 255°F. Acid fumes also cause polymerization at ordinary temperatures [USCG, 1999]. May produce highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Health Hazard

Inhalation (unlikely unless a heavy mist is formed) causes symptoms similar to those observed after ingestion. Contact with liquid or powder causes irritation of eyes and (on prolonged contact) irritation and burns of skin. Burns are slow to develop and slow to heal. May sensitize on repeated contact. Ingestion causes depression, anorexia, and diarrhea, appearing 2-3 days before death, followed by terminal dyspnea, incoordination, epistaxis, salivation, prostration and cyanosis.

Fire Hazard

Special Hazards of Combustion Products: Phosphoric acid mist may form in fire. Toxic oxides of nitrogen may form.

Safety Profile

Poison by ingestion, skin contact, intravenous, and intraperitoneal routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic and neoplastigenic data. Human mutation data reported. A corrosive irritant to the skin, eyes, and mucous membranes. When heated to decomposition it emits very toxic fumes of POx and NOx. Used as an acaricide and in the permanentpress treatment of cotton.

InChI:InChI=1/3C2H3N.H3O4P/c3*1-2-3;1-5(2,3)4/h3*3H,1H2;(H3,1,2,3,4)

Synthetic route

ethyleneimine (151-56-4) → N,N',N''-triethylenephosphoramide (545-55-1)

Conditions	Yield
With ammonia; trichlorophosphate; benzene
With triethylamine; trichlorophosphate; benzene

Thiotepa (52-24-4) → N,N',N''-triethylenephosphoramide (545-55-1) + C6H15Cl3N3OP (27780-83-2) + C6H15Cl3N3PS (93598-04-0) + C6H13ClN3OP (118694-55-6) + C6H13ClN3PS (90877-51-3) + C6H14Cl2N3PS (93598-03-9)

Conditions	Yield
In hydrogenchloride at 37℃; for 1h; Product distribution; different concentration of acid;

N,N',N''-triethylenephosphoramide (545-55-1) → C6H18N3OPS3 (13884-65-6)

Conditions	Yield
With hydrogenchloride; lithium thiophosphate powder In water; N,N-dimethyl-formamide at 25℃;	92%

N,N',N''-triethylenephosphoramide (545-55-1) → C6H15N3O10P4S3(6-)*6Li(1+) (83822-74-6)

Conditions	Yield
With hydrogenchloride; lithium thiophosphate powder In water for 0.333333h; Ambient temperature;	62%

N,N',N''-triethylenephosphoramide (545-55-1) → C6H15Br3N3OP (57856-86-7)

Conditions	Yield
With hydrogen bromide Ambient temperature;

N,N',N''-triethylenephosphoramide (545-55-1) → C6H21N3O10P4S3

Conditions	Yield
With hydrogenchloride; trisodium thiophosphate Ambient temperature;

Upstream product

• 151-56-4 ethyleneimine 
• 52-24-4 Thiotepa 

Relevant articles and documents

Particles with improved solubilization capacity

A particle is disclosed that comprises a first volume of hydrophobe-rich material with tunable dissolution and solubilization characteristics and a distinct second volume of nanostructured nonlamellar liquid crystalline material, said second volume containing said first domain and being capable of being in equilibrium with said first volume. Preferably, the nanostructured nonlamellar liquid crystalline material is capable of being in equilibrium with a polar solvent or a water-immiscible solvent or both.