Tricresyl phosphate

Tri-ortho-cresyl phosphate
Skeletal formula of tricresyl phosphate
Ball-and-stick model of the tri-ORTHO-cresyl phosphate molecule
Names
Preferred IUPAC name
Tris(2-methylphenyl) phosphate
Other names
tri-o-cresyl phosphate
TOCP
tritolyl phosphate, ortho-isomer
tri-o-tolyl ester of phosphoric acid
triorthocresyl phosphate (TOCP)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.014.136 Edit this at Wikidata
RTECS number
  • o-: TD0350000
UNII
UN number 2574
  • InChI=1S/C21H21O4P/c1-16-10-4-7-13-19(16)23-26(22,24-20-14-8-5-11-17(20)2)25-21-15-9-6-12-18(21)3/h4-15H,1-3H3 checkY
    Key: YSMRWXYRXBRSND-UHFFFAOYSA-N checkY
  • o-: InChI=1/C21H21O4P/c1-16-10-4-7-13-19(16)23-26(22,24-20-14-8-5-11-17(20)2)25-21-15-9-6-12-18(21)3/h4-15H,1-3H3
    Key: YSMRWXYRXBRSND-UHFFFAOYAP
  • o-: Cc3ccccc3OP(=O)(Oc1ccccc1C)Oc2ccccc2C
Properties
C21H21O4P
Molar mass 368.37 g/mol
Appearance colourless liquid
Melting point −40 °C (−40 °F; 233 K)
Boiling point 255 °C (491 °F; 528 K) (10 mmHg)
Hazards
GHS labelling:
GHS08: Health hazardGHS09: Environmental hazard
Danger
H370, H411
P260, P264, P270, P273, P307+P311, P321, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point > 225 °C (437 °F; 498 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Tricresyl phosphate (TCP), is a mixture of three isomeric organophosphate compounds most notably used as a flame retardant.[1] Other uses include as a plasticizer in manufacturing for lacquers and varnishes and vinyl plastics and as an antiwear additive in lubricants. Pure tricresyl phosphate is a colourless, viscous liquid, although commercial samples are typically yellow. It is virtually insoluble in water, but easily soluble in organic solvents like toluene, hexane, and diethyl ether among others. It was synthesized by Alexander Williamson in 1854 upon reacting phosphorus pentachloride with cresol (a mixture of para-, ortho-, and meta- isomers of methylphenol), though today's manufacturers can prepare TCP by mixing cresol with phosphorus oxychloride or phosphoric acid as well. TCP, especially the all-ortho isomer, is the causative agent in a number of acute poisonings. Its chronic toxicity is also of concern. The ortho-isomer is rarely used on its own outside of laboratory studies that require isomeric purity, due to its extremely toxic nature, and is generally excluded from commercial products where TCP is involved.

  1. ^ Weil, Edward D. (1978). "Phosphorus-Based Flame Retardants". Flame - Retardant Polymeric Materials. pp. 103–131. doi:10.1007/978-1-4684-6973-8_4. ISBN 978-1-4684-6975-2.