Tris(2-chloroethyl) phosphate

For the reducing agent frequently used in biochemistry and molecular biology applications, see TCEP.

Tris(2-chloroethyl) phosphate

Names
Preferred IUPAC name Tris(2-chloroethyl) phosphate
Other names 2-Chloroethanol phosphate; Tris(β-chloroethyl) phosphate; Tri(2-chloroethyl) phosphate; Tris(2-chloroethyl) orthophosphate; TCEP
Identifiers
CAS Number	115-96-8  Y
3D model (JSmol)	Interactive image
ChemSpider	7994
ECHA InfoCard	100.003.744
PubChem CID	8295
UNII	32IVO568B0  Y
CompTox Dashboard (EPA)	DTXSID5021411
InChI InChI=1S/C6H12Cl3O4P/c7-1-4-11-14(10,12-5-2-8)13-6-3-9/h1-6H2 Key: HQUQLFOMPYWACS-UHFFFAOYSA-N InChI=1/C6H12Cl3O4P/c7-1-4-11-14(10,12-5-2-8)13-6-3-9/h1-6H2 Key: HQUQLFOMPYWACS-UHFFFAOYAR
SMILES ClCCOP(=O)(OCCCl)OCCCl
Properties
Chemical formula	C6H12Cl3O4P
Molar mass	285.48 g·mol−1
Density	1.39 g/mL [1]
Boiling point	192 °C (378 °F; 465 K) 10 mmHg [1]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H351, H360, H411
Precautionary statements	P201, P202, P270, P273, P301+P312, P308+P313, P391
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tris(2-chloroethyl) phosphate (TCEP) is a chemical compound used as a flame retardant, plasticizer, and viscosity regulator in various types of polymers including polyurethanes, polyester resins, and polyacrylates. ^[2]

Safety

Because of its suspected reproductive toxicity, it is listed as a substance of very high concern under the European Union's REACH regulations. Its use has been largely replaced by tris(chloropropyl) phosphate, which has, however, been found to have similar toxic effects. ^[3]

See also

• Tris(2,3-dibromopropyl) phosphate

References

1. "Tris(2-chloroethyl) phosphate". Sigma-Aldrich . Retrieved February 25, 2013.
2. Opinion on tris(2-chloroethyl)phosphate (TCEP) in Toys (PDF) (Report). European Commission, Scientific Committee on Health and Environmental Risks. 22 March 2012. Retrieved February 25, 2013.
3. Krivoshiev, Boris V.; Beemster, Gerrit T.S.; Sprangers, Katrien; Blust, Ronny; Husson, Steven J. (April 2018). "A toxicogenomics approach to screen chlorinated flame retardants tris(2-chloroethyl) phosphate and tris(2-chloroisopropyl) phosphate for potential health effects". Journal of Applied Toxicology. 38 (4): 459–470. doi:10.1002/jat.3553. PMID   29143341. S2CID   3320347.