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
• Article Data: 4

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

Tris(2-chloropropyl) Phosphate, is a human urinary organophosphate flame retardant metabolite.

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.

Process for preparing phosphor containing alkoxylation products

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