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Tris(chloropropyl) phosphate

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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.033.766 Edit this at Wikidata
EC Number
  • 237-158-7
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H18Cl3O4P/c1-7(4-10)14-17(13,15-8(2)5-11)16-9(3)6-12/h7-9H,4-6H2,1-3H3Key: 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
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 GHS07: Exclamation mark
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 , 100 kPa). Infobox references
Chemical compound

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

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).

References

  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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