55864-04-5

Basic information

• Product Name: Phosphoric acid, 4-(1-methylethyl)phenyl diphenyl ester
• Synonyms: Brn 2478291;Diphenyl p-isopropylphenyl phosphate;p-Cumenyl phenyl phosphate (7ci);Phosphoric acid, 4-(1-methylethyl)phenyl diphenyl ester;p-Isopropylphenyl diphenyl phosphate;4-Isopropylphenyl diphenyl phosphate;Diphenyl 4-isopropylphenyl phosphate
• CAS NO: 55864-04-5
• Molecular Formula: C₂₁H₂₁O₄P
• Molecular Weight: 368.362801
• EINECS: 248-848-2
• Mol File: 55864-04-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 369.5°C (estimate)
• Flash Point: 222.7°C
• Appearance: /
• Density: 1.179 (estimate)
• Vapor Pressure: 5.94E-07mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: Phosphoric acid, 4-(1-methylethyl)phenyl diphenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid, 4-(1-methylethyl)phenyl diphenyl ester(55864-04-5)
• EPA Substance Registry System: Phosphoric acid, 4-(1-methylethyl)phenyl diphenyl ester(55864-04-5)

Safety Data

• Hazardous Substances Data: 55864-04-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H21O4P/c1-17(2)18-13-15-21(16-14-18)25-26(22,23-19-9-5-3-6-10-19)24-20-11-7-4-8-12-20/h3-17H,1-2H3

Upstream product

• 99-89-8 4-Isopropylphenol 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 88-69-7 2-(1-methylethyl)phenol 
• 2934-05-6 2,4-diisopropylphenol 
• 2078-54-8 2,6-diisopropylphenol 
• 2934-07-8 2,4,6-triisopropylphenol 
• 618-45-1 3-isopropylhydroxybenzene 
• 108-95-2 phenol 

Downstream Products

• 7116-95-2 4-isopropylbiphenyl 

Relevant articles and documents

Metal-free synthesis of biarenes via photoextrusion in di(tri)aryl phosphates

A metal-free route for the synthesis of biarenes has been developed. The approach is based on the photoextrusion of a phosphate moiety occurring upon irradiation of biaryl- A nd triaryl phosphates. The reaction involves an exciplex as the intermediate and it is especially suitable for the preparation of electron-rich biarenes.

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.