Tricresyl phosphate

Tri-ortho-cresyl phosphate
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
CAS Number	o-: 78-30-8 ; mixed isomers: 1330-78-5 ;
3D model (JSmol)	o-: Interactive image;
ChEMBL	o-: ChEMBL3181798;
ChemSpider	o-: 21106216 ;
ECHA InfoCard	100.014.136
PubChem CID	o-: 6527;
RTECS number	o-: TD0350000;
UNII	o-: X8II18JD0A ; mixed isomers: 512641US16 ;
UN number	2574
CompTox Dashboard (EPA)	o-: DTXSID6032192;
	InChI 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 Key: YSMRWXYRXBRSND-UHFFFAOYSA-N ; 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;
	SMILES o-: Cc3ccccc3OP(=O)(Oc1ccccc1C)Oc2ccccc2C;
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H370, H411
Precautionary statements	P260, P264, P270, P273, P307+P311, P321, P391, P405, P501
NFPA 704 (fire diamond)	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). verify (what is ?) Infobox references

Tricresyl phosphate (TCP), is a mixture of organophosphate compounds most notably used as a flame retardant. 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. The ortho isomer of TCP is a rather toxic substance with a long history of causing mass poisonings.