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Tricresyl phosphate information


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
Identifiers
CAS Number
  • o-: 78-30-8 checkY
  • mixed isomers: 1330-78-5 checkY
3D model (JSmol)
  • o-: Interactive image
ChEMBL
  • o-: ChEMBL3181798
ChemSpider
  • o-: 21106216 checkY
ECHA InfoCard 100.014.136 Edit this at Wikidata
PubChem CID
  • o-: 6527
RTECS number
  • o-: TD0350000
UNII
  • o-: X8II18JD0A checkY
  • mixed isomers: 512641US16 checkY
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 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
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
GHS08: Health hazardGHS09: Environmental hazard
Signal word
Danger
Hazard statements
H370, H411
Precautionary statements
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 ?)
Infobox references

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 diethylether 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.

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Tricresyl phosphate

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too volatile, eventually selecting a mixture containing triorthocresyl phosphate (TOCP), a plasticizer used in lacquers and paint finishing. Gross was...

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Dichlorvos

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Dichlorvos (2,2-dichlorovinyl dimethyl phosphate, commonly abbreviated as an DDVP) is an organophosphate widely used as an insecticide to control household...

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Oil soldiers

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Käseschnitten (fried bread with cheese) in which mineral oil mixed with tricresyl phosphate, intended as a coolant for machine guns, was mistakenly used for...

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Plasticizer

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plasticizer) Organophosphates include the following: Tricresyl phosphate (TCP) 2-Ethylhexyl diphenyl phosphate 1,2-Cyclohexane dicarboxylic acid diisononyl ester...

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Neostigmine

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Electrical tape

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curtains to cable insulation. A major ingredient in vinyl film was tricresyl phosphate (TCP), which was used as a plasticizer. Unfortunately, TCP tended...

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Phosphorus trichloride

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gives POCl3, which is used for the manufacture of triphenyl phosphate and tricresyl phosphate, which find application as flame retardants and plasticisers...

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Antiknock agent

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gasoline together with tetraethyllead. The most common ones are: Tricresyl phosphate 1,2-Dibromoethane 1,2-Dichloroethane As tetraethyllead use declined...

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Botulinum toxin

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List of gasoline additives

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Nerve agent

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symptoms by reducing the effects of acetylcholine, while oximes displaces phosphate molecules from the active site of the cholinesterase enzymes, allowing...

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Flame retardant

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such as triphenyl phosphate (TPP), resorcinol bis(diphenylphosphate) (RDP), bisphenol A diphenyl phosphate (BADP), and tricresyl phosphate (TCP); phosphonates...

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Cholinergic

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Fume event

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engine oil is an irritant and contains neurotoxic chemicals such as tricresyl phosphate. The aviation industry claims that engine oil does not contain sufficient...

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Pralidoxime

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the fully functional enzyme. Some phosphate-acetylcholinesterase conjugates continue to react after the phosphate docks to the esteric site, evolving...

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Parathion

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paraoxon. (C2H5O)2P(S)OC6H4NO2 + 1/2 O2 → (C2H5O)2P(O)OC6H4NO2 + S The phosphate ester is more reactive in organisms than the phosphorothiolate ester,...

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Bleed air

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not a medically recognized syndrome. One potential contaminant is tricresyl phosphate. Many lobbying groups have been set up to advocate for research into...

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