2502-15-0

Basic information

• Product Name: tris(4-isopropylphenyl) phosphate
• Synonyms: Tris(4-isopropylphenyl) phosphate; Phenol, 4-(1-methylethyl)-, phosphate (3:1)
• CAS NO: 2502-15-0
• Molecular Formula: C₂₇H₃₃O₄P
• Molecular Weight: 452.528
• EINECS: 219-703-0
• Mol File: 2502-15-0.mol

Chemical Properties

• CAS DataBase Reference: tris(4-isopropylphenyl) phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: tris(4-isopropylphenyl) phosphate(2502-15-0)
• EPA Substance Registry System: tris(4-isopropylphenyl) phosphate(2502-15-0)

Safety Data

• Hazardous Substances Data: 2502-15-0(Hazardous Substances Data)

Upstream product

• 99-89-8 4-Isopropylphenol 
• 75190-80-6 bis(4-isopropylphenyl)phosphoryl chloride 
• 10025-87-3 trichlorophosphate 
• 2502-16-1 C₂₇H₃₃O₃P 

Relevant articles and documents

Analysis of organophosphate hydraulic fluids in U.S. Air Force base soils

Tri-aryl and tri-alkyl organophosphates (TAPs) have been used extensively as flame-retardant hydraulic fluids and fluid additives in commercial and military aircraft. Up to 80% of the consumption of these fluids has been estimated to be lost to unrecovere

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.

Method for preparing phosphate ester derivatives from white phosphorus

A method for preparing phosphate ester derivatives from white phosphorus relates to the field of chemical engineering, and comprises the following steps: adding alkali, a catalyst, a white phosphorus solution, ROH or RSH (R represents alkyl or aromatic group) into a reaction container in an inert atmosphere, and heating and stirring the mixture in a mixed solvent of toluene and DMSO (dimethyl sulfoxide) to react for a certain time, so as to obtain three-coordinated phosphate ester derivatives; and 2) continuing to add H2O2, air or sulfur powder until the oxidation is completed, thereby obtaining the tetra-coordinated phosphate ester derivative. According to the method, chlorine, phosphorus trichloride and halogen are not needed, phosphite ester is directly prepared from elementary white phosphorus in an efficient, green and environment-friendly manner, and phosphate and thiophosphate can be directly prepared after oxidation. High pollution and high corrosivity of a traditional method are avoided in the whole process; meanwhile, white phosphorus is completely converted in the whole process, white phosphorus residues are avoided, and the post-reaction treatment process is safe.

Effects of triaryl phosphates on mouse and human nuclear receptors

The constitutively active receptor (CAR) is a crucial regulator of genes encoding for enzymes active in drug/steroid oxidation, conjugation, and transport. In our attempt to isolate the endogenous inhibitory ligand(s) for the mouse CAR, we found surprisingly that the inhibitory activity was associated with di- and tri-isopropylated phenyl phosphates that were present in livers of untreated mice. Trans-activation experiments in mammalian cells with synthetic compounds verified that mouse CAR was inhibited by various isopropylated phenyl phosphates (40-80%). Such triaryl phosphates are widely used as fire retardants, lubricants, and plasticizers, and some of them are known to disturb reproduction by currently unknown mechanisms. Equipped with the finding that these compounds could interact with mouse CAR, we proceeded to determine their functional effects on other nuclear receptors. Human CAR and pregnane X receptor (PXR) were variably activated (2-5-fold) by triaryl phosphates while mouse PXR, peroxisome proliferator-activated receptor-α, and vitamin D receptor were refractory. Among steroid hormone receptors, the human androgen receptor was inhibited by triphenyl phosphate and di-ortho-isopropylated phenyl phosphate (40-50%) and activated by di- and tri-para-substituted phenyl phosphates (2-fold). Our results add to the list of CAR and PXR activators and suggest steroid-dependent biological pathways that may contribute to the reproductive effects of triaryl phosphates.

KINETICS OF ESTERIFICATION OF MONOISOPROPYLPHENOLS WITH PHOSPHORYL TRICHLORIDE

The kinetics of liquid-phase isothermal esterification of POCl3 with 2-isopropylphenol and 4-isopropylphenol have been studied within the temperature intervals of 110 to 130 and 90 to 110 deg C, respectively.The rate constants and activation energies of the individual steps of this three-step reaction have been calculated from the values measured.The reaction rates of the two isomers markedly differ: at 110 deg C 4-isopropylphenol reacts faster by the factors of about 7 and 20 for k1 and k3 respectively.This finding can be utilized in preparation of mixed triarylphosphates, since the alkylation mixture after reaction of phenol with propene contains an excess of 2-isopropylphenol over 4-isopropylphenol.