78-32-0

Basic information

• Product Name: TRI-P-TOLYL PHOSPHATE
• Synonyms: phosphoricacid,tri(4-tolyl)ester;Phosphoricacid,tris(4-methylphenyl)ester;phosphoricacidtris-(4-methylphenyl)ester;p-Tolyl phosphate ((C7H7O)3PO);tpcp;Tris(4-methylphenyl) phosphate;Tris(p-cresyl) phosphate;Tris(p-methylphenyl) phosphate
• CAS NO: 78-32-0
• Molecular Formula: C₂₁H₂₁O₄P
• Molecular Weight: 368.36
• EINECS: 201-105-6
• Mol File: 78-32-0.mol
• Article Data: 20

Chemical Properties

• Melting Point: 74-78 °C
• Boiling Point: 430 °C
• Flash Point: 410 °C
• Appearance: /solid
• Density: 1.2470
• Water Solubility: 0.3 mg l-1
• CAS DataBase Reference: TRI-P-TOLYL PHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRI-P-TOLYL PHOSPHATE(78-32-0)
• EPA Substance Registry System: TRI-P-TOLYL PHOSPHATE(78-32-0)

Safety Data

• Hazard Codes: N-Xn,N,Xn
• Statements: 51/53-21/22
• Safety Statements: 61-28A-28
• RIDADR: 3082
• RTECS: TC9330000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 78-32-0(Hazardous Substances Data)

Usage

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Organophosphates, such as TRI-P-TOLYL PHOSPHATE, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Health Hazard

SYMPTOMS: Nausea, vomiting, abdominal pain, diarrhea. After 3-28 days incubation period: non-tender enlargement of parotid gland; coldness and sweating of hands and legs; muscular pain and cramping of hands and legs; parethesias of extremities; muscular tremor; symmetrical polyneuritis.

Fire Hazard

Flash point data for TRI-P-TOLYL PHOSPHATE are not available, however, TRI-P-TOLYL PHOSPHATE is probably combustible.

InChI:InChI=1/C21H21O4P/c1-16-4-10-19(11-5-16)23-26(22,24-20-12-6-17(2)7-13-20)25-21-14-8-18(3)9-15-21/h4-15H,1-3H3

Upstream product

• 106-44-5 p-cresol 
• 7732-18-5 water 
• 10025-87-3 trichlorophosphate 
• 620-42-8 tri-p-tolylphosphite 
• 86508-64-7 3-phenyl-5-trifluoromethyl-2,2,2-tris(4-methylphenoxy)-2,3-dihydro-1,3,4,2-oxadiazaphosphole 
• 624-49-7 dimethylfumarate 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 1192-96-7 potassium p-cresolate 
• 1121-70-6 sodium 4-methylphenoxide 
• 597-84-2 O,O,O-tri(p-methylphenyl) phosphorothioate 
• 100-42-5 styrene 
• 28097-68-9 1,1,2,2-Tetrachloro-propyl-phosphorimidic acid tri-p-tolyl ester 

Downstream Products

• 106-44-5 p-cresol 
• 84022-55-9 2-(p-tolyloxy)quinoline 
• 67698-82-2 1-methyl-4-(octyloxy)benzene 
• 3402-74-2 4-(4-nitrophenoxy)toluene 
• 4496-49-5 4-tert-butyldiphenylamine 
• 23600-89-7 1‐[4‐[(4‐methylphenyl)amino]phenyl]ethanone 
• 634-43-5 N-(p-tolyl)naphthalen-1-amine 
• 147678-90-8 N-(4-(methyl)phenyl)-[1,1′-biphenyl]-4-amine 
• 3077-16-5 4-(4-methylphenyl)morpholine 
• 2432-14-6 3,5-dibromo-4-hydroxytoluene 
• 84022-59-3 2,5-Diphenyl-3-p-tolyloxy-pyrazine 
• 834-25-3 4-methylphenyl benzyl ether 
• 112381-04-1 C₂₁H₂₁O₄P 
• 84022-57-1 2,5-Diisobutyl-3-p-tolyloxy-pyrazine 

Relevant articles and documents

Diphenyl Diselenide-Catalyzed Synthesis of Triaryl Phosphites and Triaryl Phosphates from White Phosphorus

Industrially important triaryl phosphites, traditionally prepared from PCl3, have been synthesized by a diphenyl diselenide-catalyzed one-step procedure involving white phosphorus and phenols, which provides a halogen- and transition metal-free way to these compounds. Subsequent oxidation of triaryl phosphites produces triaryl phosphates and triaryl thiophosphates. Phosphorotrithioates are also prepared efficiently from aromatic thiols and aliphatic thiols.

Nickel-catalyzed amination of aryl phosphates through cleaving aryl C-O bonds

The amination of triaryl phosphates was achieved using a Ni(II)-(σ-Aryl) complex/NHC catalyst system in dioxane at 110 °C in the presence of NaH as base. Electron-neutral, -rich, and -deficient triaryl phosphates were coupled with a wider range of amine partners including cyclic and acyclic secondary amines, aliphatic primary amines, and anilines in good to excellent yields.

Aerobic photooxidation of phosphite esters using diorganotelluride catalysts

Diorganotellurides containing bulky aromatic substituents are found to catalyze the photooxidation of phosphite esters using aerobic oxygen as a terminal oxidant. A Hammett plot with substituted triaryl phosphites yielding p = 2.88 agrees with a nucleophilic oxygen transfer from telluroxide to phosphite.2009 American Chemical Society.