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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.744 Edit this at Wikidata
UNII
  • 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
  • ClCCOP(=O)(OCCCl)OCCCl
Properties
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:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H351, H360, H411
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).

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 is safer.[3]

See also

References

  1. ^ a b "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.