6395-59-1

Basic information

• Product Name: bis(4-chlorophenyl) methylphosphonate
• Synonyms: Bis(p-chlorophenyl) methylphosphonate; Phosphonic acid, methyl-, bis(p-chlorophenyl) ester
• CAS NO: 6395-59-1
• Molecular Formula: C₁₃H₁₁Cl₂O₃P
• Molecular Weight: 317.1044
• Mol File: 6395-59-1.mol

Chemical Properties

• Boiling Point: 404.2°C at 760 mmHg
• Flash Point: 308.8°C
• Density: 1.379g/cm³
• Vapor Pressure: 2.25E-06mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: bis(4-chlorophenyl) methylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: bis(4-chlorophenyl) methylphosphonate(6395-59-1)
• EPA Substance Registry System: bis(4-chlorophenyl) methylphosphonate(6395-59-1)

Safety Data

• Hazardous Substances Data: 6395-59-1(Hazardous Substances Data)

Upstream product

• 5679-61-8 tris(p-chlorophenyl)phosphite 
• 676-97-1 methylphosphonic acid dichloroanhydride 
• 106-48-9 4-chloro-phenol 
• 623-12-1 4-chloromethoxybenzene 

Downstream Products

• 1070428-60-2 p-chlorophenyl methylphosphonate sodium salt 

Relevant articles and documents

Mechanistic study of Protein Phosphatase-1 (PP1), a catalytically promiscuous enzyme

The reaction catalyzed by the protein phosphatase-1 (PP1) has been examined by linear free energy relationships and kinetic isotope effects. With the substrate 4-nitrophenyl phosphate (4NPP), the reaction exhibits a bell-shaped pH-rate profile for kcat/KM indicative of catalysis by both acidic and basic residues, with kinetic pKa values of 6.0 and 7.2. The enzymatic hydrolysis of a series of aryl monoester substrates yields a Bronsted βlg of -0.32, considerably less negative than that of the uncatalyzed hydrolysis of monoester dianions (-1.23). Kinetic isotope effects in the leaving group with the substrate 4NPP are 18(V/K)bridge = 1.0170 and 15(V/K) = 1.0010, which, compared against other enzymatic KIEs with and without general acid catalysis, are consistent with a loose transition state with partial neutralization of the leaving group. PP1 also efficiently catalyzes the hydrolysis of 4-nitrophenyl methylphosphonate (4NPMP). The enzymatic hydrolysis of a series of aryl methylphosphonate substrates yields a Bronsted βlg of -0.30, smaller than the alkaline hydrolysis (-0.69) and similar to the βlg measured for monoester substrates, indicative of similar transition states. The KIEs and the βlg data point to a transition state for the alkaline hydrolysis of 4NPMP that is similar to that of diesters with the same leaving group. For the enzymatic reaction of 4NPMP, the KIEs are indicative of a transition state that is somewhat looser than the alkaline hydrolysis reaction and similar to the PP1-catalyzed monoester reaction. The data cumulatively point to enzymatic transition states for aryl phosphate monoester and aryl methylphosphonate hydrolysis reactions that are much more similar to one another than the nonenzymatic hydrolysis reactions of the two substrates.

One pot synthesis of diastereomeric phosphonates

The reaction of diaryl methylphosphonate with sterically hindered alcohols in presence of sodium hydride provide arylalkyl methylphosphonate esters with high diastereoselectivity at the phosphorus center.

New feature of Friedel-Crafts phosphonation of anisoles: Unexpected in situ methylphosphorylation reaction

Anisoles 1, reacting with AlCl3 and PCl3 with appropriate reagent ratios, give, in good yields, the corresponding diaryl methylphosphonates 2 or the methylphoshinates 3b,c and the methylphosphine oxides 4b,c. This unexpected in situ methylphosphorylation explains the reported limited and conflicting results to obtain methoxy-substituted arylphosphonous dichloride with the same reagents. A suggested mechanism is also reported.

PHOTOLYSIS OF ARYL ESTERS OF TRI- AND TETRACOORDINATED PHOSPHORUS COMPOUNDS

Upon UV excitation in methanol, some diaryl esters of alkly- or alkenyl phosphonates underwent an elimination of two aryl groups to give biaryls and the corresponding alkyl- or alkenylphosphonic acids.Tris(4-methoxyphenyl) phosphite also underwent a similar elimination to give 4,4'-dimethoxybiphenyl and 4-methoxyphenyl phosphonate.This interesting biaryl elimination was confirmed to proceed via a singlet intramolecular excimer by means of fluorescence spectra and Stern-Volmer analysis.

Process for preparing diaryl methylphosphonate and derivatives thereof

A process is provided for the preparation of diaryl methylphosphonates through the reaction of triaryl phosphites with methanol in the presence of a catalytic quantity of methyl iodide. The reaction is conducted at a temperature of from about 170° C. to about 250° C. New and useful derivatives are produced by reaction of the diaryl methylphosphonates with polyols or amines.