Tris(chloropropyl) phosphate

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]

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

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]