115-96-8

Basic information

• Product Name: Tris(2-chloroethyl) phosphate
• Synonyms: 3CF;ai3-15023;antiblaze100;Celluflex;Celluflex CEF;celluflexcef;Disflamoll TCA;disflamolltca
• CAS NO: 115-96-8
• Molecular Formula: C6H12Cl3O4P
• Molecular Weight: 285.49
• EINECS: 204-118-5
• Product Categories: Organics;Functional Materials;Phosphates (Plasticizer);Plasticizer;Organic Building Blocks;Organic Phosphates/Phosphites;Phosphorus Compounds;organophosphorus compound;Metabolites & Impurities;Phosphorylating and Phosphitylating Agents;Building Blocks;Chemical Synthesis;Organic Building Blocks;Organic Phosphates/Phosphites;Phosphorus Compounds;Metabolites & Impurities, Phosphorylating and Phosphitylating Agents
• Mol File: 115-96-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: -51 °C
• Boiling Point: 192 °C10 mm Hg(lit.)
• Flash Point: 450 °F
• Appearance: Clear colorless/Liquid
• Density: 1.39 g/mL at 25 °C(lit.)
• Vapor Pressure: <10 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.472(lit.)
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble7.82g/L
• Water Solubility: 7 g/L (20 ºC)
• Stability: Stable. Incompatible with strong bases, strong oxidizing agents.
• CAS DataBase Reference: Tris(2-chloroethyl) phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Tris(2-chloroethyl) phosphate(115-96-8)
• EPA Substance Registry System: Tris(2-chloroethyl) phosphate(115-96-8)

Safety Data

• Hazard Codes: Xn,N,T
• Statements: 22-40-51/53-60
• Safety Statements: 36/37-61-45-53
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: KK2450000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 115-96-8(Hazardous Substances Data)

Usage

Description

Tris(2-chloroethyl) phosphate, also known as TCEP, is a colorless, odorless liquid with a neutral pH. It is a trialkyl phosphate that is the tris(2-chloroethyl) ester of phosphoric acid. Tris(2-chloroethyl) phosphate is slightly water-soluble and combustible, making it a versatile chemical with various applications across different industries.

Uses

Used in Environmental Monitoring:
Tris(2-chloroethyl) phosphate is used as a sampling agent for dynamic air sampling of airborne organophosphate triesters. This application utilizes a solid-phase microextraction device to detect and monitor the presence of these potentially harmful compounds in the environment.
Used in Human Health Research:
In the field of human health research, Tris(2-chloroethyl) phosphate is used as a marker for a human urinary organophosphate flame retardant metabolite. This application aids in understanding the exposure and potential health effects of organophosphate flame retardants in humans.
Used in Chemical Synthesis:
Due to its chemical properties, Tris(2-chloroethyl) phosphate can be used as an intermediate in the synthesis of various compounds, particularly in the pharmaceutical and agrochemical industries. Its reactivity and stability make it a valuable component in the development of new products.
Used in Flame Retardants:
Tris(2-chloroethyl) phosphate is also utilized as a component in the formulation of flame retardants. Its combustibility and chemical properties make it suitable for use in materials that require enhanced fire resistance, such as plastics, textiles, and electronic components.

Reactivity Profile

Tris(2-chloroethyl) phosphate is incompatible with strong oxidizing agents and strong bases.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data. A skin and eye irritant. Combustible when exposed to heat or flame. When heated to decomposition it emits very toxic fumes of POx and Cl-. See also PHOSPHATES, CHLORIDES, and ESTERS.

InChI:InChI=1/C6H12Cl3O4P/c1-4(7)11-14(10,12-5(2)8)13-6(3)9/h4-6H,1-3H3

Synthetic route

oxirane (75-21-8) → Tris(2-chloroethyl) phosphate (115-96-8)

Conditions	Yield
With trichlorophosphate at 10℃; for 2h; Autoclave; Reflux;	99.2%
With titanium tetrachloride; trichlorophosphate at 50 - 65℃; for 9h;	94%
With trichlorophosphate at 100℃;

2-chloro-ethanol (107-07-3) → Tris(2-chloroethyl) phosphate (115-96-8)

Conditions	Yield
With trichlorophosphate 1.) 25-30 deg C, 3 h, 2.) 50-60 deg C, 6 h;	91%
With trichlorophosphate at 25 - 40℃;
With tetrachloromethane; trichlorophosphate bei Siedetemperatur;

tris(2-chloro-ethyl)phosphite (140-08-9) → Tris(2-chloroethyl) phosphate (115-96-8)

Conditions	Yield
With potassium permanganate
With chlorine; 2-chloro-ethanol
With phosphoric acid In nitromethane

ethene (74-85-1) → Tris(2-chloroethyl) phosphate (115-96-8)

Conditions	Yield
With phosphoric acid; chlorine

2-chloro-ethanol (107-07-3) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → Tris(2-chloroethyl) phosphate (115-96-8)

diethyl ether (60-29-7) + tris(2-chloro-ethyl)phosphite (140-08-9) + aqueous potassium permanganate → Tris(2-chloroethyl) phosphate (115-96-8)

cobalt(II) chloride hexahydrate + Tris(2-chloroethyl) phosphate (115-96-8) → tetrakis[tri(2-chloroethyl)phosphate]diaquacobalt(II) tetrachlorocobaltate(II)

Conditions	Yield
at 80℃; for 20h;	100%

chloral hydrate (302-17-0) + Tris(2-chloroethyl) phosphate (115-96-8) → (2,2,2-trichloro-1-hydroxy-ethyl)-phosphonic acid bis-(2-chloro-ethyl) ester (14114-78-4)

Conditions	Yield
In hexane Heating;	82%

Tris(2-chloroethyl) phosphate (115-96-8) + sodium p-aminobenzoate (555-06-6) → tris[2-(p-aminobenzoyloxy)ethyl] phosphate

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; N-benzyl-N,N,N-triethylammonium chloride In N,N-dimethyl-formamide 1.) 110 deg C, 2 h, 2.) 130 deg C, 1 h;	46%

Tris(2-chloroethyl) phosphate (115-96-8) + 1-cyclohexylcyclohexane-1-carboxylic acid (60263-54-9) → bicyclohexyl-1-carboxylic acid-(2-chloro-ethyl ester)

Conditions	Yield
With sodium carbonate

Tris(2-chloroethyl) phosphate (115-96-8) → phosphoric acid mono-(2-hydroxy-ethyl) ester (1892-26-8)

Conditions	Yield
With barium dihydroxide

Tris(2-chloroethyl) phosphate (115-96-8) → phosphoric acid bis-(2-hydroxy-ethyl ester); barium salt

Conditions	Yield
With silver(l) oxide nachfolgendes Umsetzen mit Barytwasser;
With water; lead(II) oxide nachfolgendes Umsetzen mit Barytwasser;

Tris(2-chloroethyl) phosphate (115-96-8) → 1,2-dichloro-ethane (107-06-2)

Conditions	Yield
erfolgt Zersetzung;

Tris(2-chloroethyl) phosphate (115-96-8) + trimethylamine (75-50-3) → phosphoric acid tris-(2-trimethylammonio-ethyl ester); tris chloride (38837-96-6)

Conditions	Yield
With ethanol at 30 - 33℃;
With benzene at 80℃;

Tris(2-chloroethyl) phosphate (115-96-8) + 1-Nitropropen (3156-70-5) → isopropenyl-phosphonic acid bis-(2-chloro-ethyl ester) (66833-71-4)

Tris(2-chloroethyl) phosphate (115-96-8) + phenylphosphonous acid dichloride; compound with aluminium trichloride (1:1) (82123-74-8) → Dichlorophenylphosphine (644-97-3) + complex of tris-2-chloroethyl phosphate with aluminum chloride

Conditions	Yield
With phosphorus trichloride at 30℃; for 0.333333h; Product distribution; complexes of various arylphosphonous dichlorides with aluminum chloride;

Tris(2-chloroethyl) phosphate (115-96-8) + water (7732-18-5) + lead oxide → phosphoric acid bis-(2-hydroxy-ethyl) ester (18924-97-5)

Tris(2-chloroethyl) phosphate (115-96-8) + silver oxide → phosphoric acid bis-(2-hydroxy-ethyl) ester (18924-97-5)

Tris(2-chloroethyl) phosphate (115-96-8) → tris[2-(p-maleamidobenzoyloxy)ethyl] phosphate

Conditions	Yield
Multi-step reaction with 2 steps 1: 46 percent / Et3BnNCl, ionol / dimethylformamide / 1.) 110 deg C, 2 h, 2.) 130 deg C, 1 h 2: 91 percent / dioxane / 3 h / 50 - 60 °C View Scheme

Tris(2-chloroethyl) phosphate (115-96-8) + nickel diacetate (373-02-4, 14998-37-9, 33025-09-1, 94044-50-5, 98268-31-6) → bis(2-chloroethoxy)phosphato nickel(II)

Conditions	Yield
In neat (no solvent) refluxing nickel(II) acetate and tris(2-chloroethyl)phosphate at 170 - 180°C in vacuo; adding ether, filtering ppt., drying in vacuo; elem. anal.;

Tris(2-chloroethyl) phosphate (115-96-8) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) → bis(2-chloroethoxy)phosphato cobalt(II)

Conditions	Yield
In neat (no solvent) refluxing cobalt(II) acetate and tris(2-chloroethyl)phosphate at 170 - 180°C in vacuo; adding ether, filtering ppt., drying in vacuo; elem. anal.;

Tris(2-chloroethyl) phosphate (115-96-8) + cobalt(II) chloride (7646-79-9) → bis(2-chloroethoxy)phosphato cobalt(II)

Conditions	Yield
In neat (no solvent) refluxing cobalt(II) chloride and tris(2-chloroethyl)phosphate at 170 - 180°C in vacuo; adding ether, filtering ppt., drying in vacuo; elem. anal.;

Tris(2-chloroethyl) phosphate (115-96-8) + nickel dichloride → bis(2-chloroethoxy)phosphato nickel(II)

Conditions	Yield
In neat (no solvent) refluxing nickel(II) chloride and tris(2-chloroethyl)phosphate at 170 - 180°C in vacuo; adding ether, filtering ppt., drying in vacuo; elem. anal.;

Tris(2-chloroethyl) phosphate (115-96-8) + chromium(III) chloride (10025-73-7) → (tris(2-chloroethoxy)phosphato)chromium(III) (114802-30-1)

Conditions	Yield
In neat (no solvent) refluxing in vac.; elem. anal.;

Tris(2-chloroethyl) phosphate (115-96-8) + vanadium(III) chloride (7718-98-1) → (tris(2-chloroethoxy)phosphato)vanadium(III) (114802-29-8)

Conditions	Yield
In neat (no solvent) refluxing in vac.; elem. anal.;

vanadyl(IV) chloride + Tris(2-chloroethyl) phosphate (115-96-8) → (bis(2-chloroethoxy)phosphato)oxovanadium(IV) (39923-16-5, 114802-31-2)

Conditions	Yield
In neat (no solvent) refluxing at 160-180°C; elem. anal.;

Upstream product

• 75-21-8 oxirane 
• 140-08-9 tris(2-chloro-ethyl)phosphite 
• 74-85-1 ethene 
• 107-07-3 2-chloro-ethanol 
• 10025-87-3 trichlorophosphate 
• 60-29-7 diethyl ether 

Downstream Products

• 1892-26-8 phosphoric acid mono-(2-hydroxy-ethyl) ester 
• 107-06-2 1,2-dichloro-ethane 
• 644-97-3 Dichlorophenylphosphine 
• 16672-87-0 2-chloroethylphosphonic acid 

Relevant articles and documents

Epoxy ether cleaving reactions catalyzed by supporting Lewis acidic ionic liquid

Lewis acidic ionic liquids were used to catalyze the reaction of epoxypropane with POCl3. Considering the lower cost and catalytic activities, we concluded that [Et3NH]Cl/AlCl3 was the most attractive ionic liquid from an economical point of view. But it would be easily inactivated because of sensitive to water and air. Moreover, it could not be reused easily because of difficulty recovery in the reaction. However, supporting [Et3NH]Cl/AlCl3 catalyst could resolve above problems. Supporting [Et3NH]Cl/AlCl3 catalyst could be separated by filter easily and reused 5 times in 98% yield. Furthermore, the catalyst was applicable to other epoxy ether cleaving reactions.

'Antispectrochemical' Behaviour of Cobalt(II) and Nickel(II) Chelates of Substituted Trialkylphosphates

The chelates of the type M2 have been prepared by the solvolysis of the corresponding divalent metal chlorides or acetate by respective trialkylphosphates.While the cobalt(II) derivatives are tetrahedral with two (RO)2P(O)2 chelating groups, the nickel(II) derivatives have a distorted octahedral geometry resulting from the possible participation of the ethereal oxygen of the alkoxy group.The organophosphate chelating groups reveal 'antispectrochemical behaviour' in these systems.