Tris(chloropropyl) phosphate

Tris(chloropropyl) phosphate
Names
	IUPAC name Tris(2-chloro-1-methylethyl) phosphate
	Other names Tris(1-chloro-2-propyl)phosphate; Tris(2-chloroisopropyl)phosphate; Tris(monochloroisopropyl) phosphate (TMCP); Tris(2-chloroisopropyl) phosphate (TCIP);
Identifiers
CAS Number	13674-84-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:143728;
ChEMBL	ChEMBL3188873;
ChemSpider	24387;
ECHA InfoCard	100.033.766
EC Number	237-158-7;
PubChem CID	26176;
UNII	CRT22GFY70;
CompTox Dashboard (EPA)	DTXSID5026259 ;
	InChI InChI=1S/C9H18Cl3O4P/c1-7(4-10)14-17(13,15-8(2)5-11)16-9(3)6-12/h7-9H,4-6H2,1-3H3 Key: KVMPUXDNESXNOH-UHFFFAOYSA-N;
	SMILES O=P(OC(CCl)C)(OC(CCl)C)OC(CCl)C;
Properties
Chemical formula	C9H18Cl3O4P
Molar mass	327.56 g·mol−1
Appearance	Liquid
Melting point	20 °C (68 °F; 293 K)
Boiling point	290 °C (554 °F; 563 K) decomposes
Solubility in water	1,080 mg/l at 20°C
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312, P330
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tris(chloropropyl) phosphate (commonly abbreviated TCPP) is a chlorinated organophosphate flame retardant commonly added to polyurethane foams.^[1] Comparatively minor amounts are used in PVC and EVA.^[2]

Synthesis

TCPP is prepared industrially by the reaction of propylene oxide with phosphoryl chloride. In practise this produces a range of products, of which the tris(2-chloro-1-methylethyl) isomer tends to dominate (50-85% w/w).^[3]

References

^ Yadav, Anilkumar; de Souza, Felipe M.; Dawsey, Tim; Gupta, Ram K. (19 October 2022). "Recent Advancements in Flame-Retardant Polyurethane Foams: A Review". Industrial & Engineering Chemistry Research. 61 (41): 15046–15065. doi:10.1021/acs.iecr.2c02670. S2CID 252832072.
^ "European Union Risk Assessment Report: TCPP". ECHA. Retrieved 1 March 2024.
^ Truong, Jimmy W.; Diamond, Miriam L.; Helm, Paul A.; Jantunen, Liisa M. (December 2017). "Isomers of tris(chloropropyl) phosphate (TCPP) in technical mixtures and environmental samples". Analytical and Bioanalytical Chemistry. 409 (30): 6989–6997. doi:10.1007/s00216-017-0572-7. PMID 29147747. S2CID 24611076.

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[1] Yadav, Anilkumar; de Souza, Felipe M.; Dawsey, Tim; Gupta, Ram K. (19 October 2022). "Recent Advancements in Flame-Retardant Polyurethane Foams: A Review". Industrial & Engineering Chemistry Research. 61 (41): 15046–15065. doi:10.1021/acs.iecr.2c02670. S2CID 252832072.

[2] "European Union Risk Assessment Report: TCPP". ECHA. Retrieved 1 March 2024.

[3] Truong, Jimmy W.; Diamond, Miriam L.; Helm, Paul A.; Jantunen, Liisa M. (December 2017). "Isomers of tris(chloropropyl) phosphate (TCPP) in technical mixtures and environmental samples". Analytical and Bioanalytical Chemistry. 409 (30): 6989–6997. doi:10.1007/s00216-017-0572-7. PMID 29147747. S2CID 24611076.

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