6145-73-9

Basic information

• Product Name: Tris(2-chloropropyl) phosphate
• Synonyms: fyrol PCF;TRIS(2-CHLORO-1-PROPYL)PHOSPHATE;1-Propanol, 2-chloro-, phosphate (3:1);Phosphoric acid tris(2-chloropropyl) ester;TMCPP;Tris(2-chloropropyl) phosphate;tris(b-Chloropropyl)phosphate 99%
• CAS NO: 6145-73-9
• Molecular Formula: C₉H₁₈Cl₃O₄P
• Molecular Weight: 327.57
• EINECS: 228-150-4
• Product Categories: Organics
• Mol File: 6145-73-9.mol

Chemical Properties

• Boiling Point: 358.5 °C at 760 mmHg
• Flash Point: 249.7 °C
• Appearance: /
• Density: 1.281 g/cm³
• Vapor Pressure: 5.25E-05mmHg at 25°C
• Refractive Index: 1.462
• Water Solubility: <0.1 g/100 mL at 19.5℃
• CAS DataBase Reference: Tris(2-chloropropyl) phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Tris(2-chloropropyl) phosphate(6145-73-9)
• EPA Substance Registry System: Tris(2-chloropropyl) phosphate(6145-73-9)

Safety Data

• Hazardous Substances Data: 6145-73-9(Hazardous Substances Data)

Usage

Uses

Used in Flame Retardants Industry:
Tris(2-chloropropyl) phosphate is used as a metabolite in the human body for the excretion of organophosphate flame retardants. These flame retardants are added to various materials, such as plastics, textiles, and electronics, to reduce their flammability and improve safety in case of fire. The presence of Tris(2-chloropropyl) phosphate in human urine indicates exposure to these flame retardants, which can be a concern for public health and environmental safety.
Used in Environmental and Public Health Research:
Tris(2-chloropropyl) phosphate serves as a biomarker for exposure to organophosphate flame retardants. Researchers in the fields of environmental and public health use this compound to study the prevalence of flame retardant exposure in human populations, assess potential health risks, and develop strategies for reducing exposure and mitigating the associated health effects.
Used in Analytical Chemistry:
Tris(2-chloropropyl) phosphate can be used as a reference compound in analytical chemistry for the development and validation of methods to detect and quantify organophosphate flame retardants and their metabolites in various environmental and biological samples. This helps in understanding the distribution, fate, and transport of these chemicals in the environment and their potential impact on human health and ecosystems.

InChI:InChI=1/C9H18Cl3O4P/c1-7(4-10)14-17(13,15-8(2)5-11)16-9(3)6-12/h7-9H,4-6H2,1-3H3

Synthetic route

methyloxirane (75-56-9, 16033-71-9) → Tris(2-chloropropyl) phosphate (6145-73-9)

Conditions	Yield
With trichlorophosphate at 10℃; for 2h; Reagent/catalyst; Autoclave; Reflux;	98.3%
With triethylamine; trichlorophosphate
With titanium tetrachloride; trichlorophosphate

1,2-propylene cyclic carbonate (108-32-7) → Tris(2-chloropropyl) phosphate (6145-73-9)

Conditions	Yield
With trichlorophosphate

methyloxirane (75-56-9, 16033-71-9) → (ClCH2CH2CH2O)(MeCHClCH2O)2PO + (ClCH2CH2CH2O)2(MeCHClCH2O)PO + Tris(2-chloropropyl) phosphate (6145-73-9) + tris(3-chloropropyl) phosphate (1067-98-7)

Conditions	Yield
With trichlorophosphate; aluminum oxide at 45 - 75℃; for 3 - 6h; Product distribution / selectivity;	A 29.7 %Chromat. B 6.3 %Chromat. C 50 %Chromat. D 0.5 %Chromat.
With trichlorophosphate; ZR(OZ)2WO3 (RO129) at 40 - 55℃; for 3h; Product distribution / selectivity;	A 13.8 %Chromat. B 5.0 %Chromat. C 14.8 %Chromat. D 1.6 %Chromat.
With trichlorophosphate; magnesium aluminate at 40 - 75℃; for 3h; Product distribution / selectivity;	A 23.9 %Chromat. B 5.2 %Chromat. C 51.7 %Chromat. D 0.5 %Chromat.

methyloxirane (75-56-9, 16033-71-9) → Tris(2-chloropropyl) phosphate (6145-73-9) + 2-methyl-2-pentenal (14250-96-5, 16958-22-8, 623-36-9) + tris-(2-chloro, 1-methylethyl)-phosphate (13674-84-5) + bis(2-chloro-1-methylethyl)(2-chloropropyl)phosphate (76025-08-6) + 2-chloro-1-methylethyl bis(2-chloropropyl)phosphate (76649-15-5)

Conditions	Yield
With trichlorophosphate; aluminum (III) chloride at 40 - 65℃; for 6h; Product distribution / selectivity;
With trichlorophosphate; titanium tetrachloride at 40 - 65℃; for 6h; Product distribution / selectivity;

methyloxirane (75-56-9, 16033-71-9) → Tris(2-chloropropyl) phosphate (6145-73-9) + tris-(2-chloro, 1-methylethyl)-phosphate (13674-84-5) + bis(2-chloro-1-methylethyl)(2-chloropropyl)phosphate (76025-08-6) + 2-chloro-1-methylethyl bis(2-chloropropyl)phosphate (76649-15-5)

Conditions	Yield
With trichlorophosphate; aluminum (III) chloride at 50 - 95℃; for 6h; Product distribution / selectivity;

Tris(2-chloropropyl) phosphate (6145-73-9) + titanium tetrachloride (7550-45-0) → bis[tri(2-chloropropyl)phosphate]tetrachlorotitanium (1022894-35-4)

Conditions	Yield
In neat (no solvent) (inert atm); TiCl4 was added to phosphate with stiring, maintained at room temp. for 1 h;

Tris(2-chloropropyl) phosphate (6145-73-9) + tin(IV) chloride (7646-78-8) → bis[tri(2-chloropropyl)phosphate]tetrachlorotin (1022894-33-2)

Conditions	Yield
In neat (no solvent) (inert atm); SnCl4 was added to phosphate with stiring, maintained at room temp. for 1 h;

Tris(2-chloropropyl) phosphate (6145-73-9) + zinc(II) chloride (7646-85-7) → bis[tri(2-chloropropyl)phosphate]dichlorozinc (1131798-16-7)

Conditions	Yield
In neat (no solvent) (inert atm); ZnCl2 was added to phosphate with stiring, heated at 1--=120°C for 1.5-2 h;

Upstream product

• 75-56-9 methyloxirane 
• 108-32-7 1,2-propylene cyclic carbonate 

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.

Preparation of phosphorus-containing propoxylation products by using aluminium trichloride

The invention describes a process for preparing propoxylated, phosphorus-containing compounds using aluminium chloride catalyst.

Preparation of tris-(chloropropyl) phosphate

Producing acid-free tri(chloropropyl)phosphate (A) comprises reacting phosphoroxychloride with propylene oxides in the presence of heterogeneous metallic oxide catalysts (I), without additional water or alkali washing of the alkoxylation product containing phosphorus. Producing acid-free tri(chloropropyl)phosphate (A) comprises reacting phosphoroxychloride with propylene oxides in the presence of heterogeneous metallic oxide catalysts of formula ([(X) l 3+>((B 1>) nb+)]O m) (I), without additional water or alkali washing of the alkoxylation product containing phosphorus. X : Al, Ti or Zr; B 1>(non)metal e.g. Li, Na, K, Mg, Ca, Sr, Ba, Sc, Y, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, B, Ga, In, Si, Ge, Sn, Pb, P, As, Sb or Bi; b : 1-6; and l, n, m : 0.0001-4. Provided that 2m is equal to the sum of 3l and nb.