75599-76-7

Basic information

• Product Name: Phosphinic acid, diphenyl-, 2,4-dinitrophenyl ester
• CAS NO: 75599-76-7
• Molecular Formula: C18H13N2O6P
• Molecular Weight: 384.285
• Mol File: 75599-76-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Phosphinic acid, diphenyl-, 2,4-dinitrophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphinic acid, diphenyl-, 2,4-dinitrophenyl ester(75599-76-7)
• EPA Substance Registry System: Phosphinic acid, diphenyl-, 2,4-dinitrophenyl ester(75599-76-7)

Safety Data

• Hazardous Substances Data: 75599-76-7(Hazardous Substances Data)

Upstream product

• 51-28-5 2,4-Dinitrophenol 
• 1499-21-4 Diphenylphosphinic chloride 
• 1079-66-9 chloro-diphenylphosphine 

Downstream Products

• 4693-63-4 Benzoesaeure-diphenylphosphinsaeure-anhydrid 
• 20350-26-9 2,4-dinitrophenolate 
• 1707-03-5 diphenyl-phosphinic acid 
• 1135-98-4 diphenylphosphinic fluoride 
• 6230-68-8 diphenyl(piperidin-1-yl)phosphine oxide 
• 227776-08-1 N-diphenylphosphinoyl-piperazine 
• 55025-89-3 morpholinodiphenylphosphine oxide 
• 51-28-5 2,4-Dinitrophenol 
• 13059-86-4 2,4-dinitro-N-butylaniline 

Relevant articles and documents

Aminolysis of Y-substituted phenyl diphenylphosphinates and benzoates: Effect of modification of electrophilic center from C=O to P=O

(Chemical Equation Presented) The effect of modification of the electrophilic center from C=O to P=O on reactivity and reaction mechanism has been investigated for aminolysis of Y-substituted phenyl diphenylphosphinates (1a-j) and benzoates (2a-i). The phosphinates 1a-j are less reactive than the benzoates 2a-i. The reactions of 2,4-dinitrophenyl diphenylphosphinate (1a) with alicyclic secondary amines resulted in a linear Bronsted-type plot with a βnuc value of 0.38, while the corresponding reactions of 2,4-dinitrophenyl benzoate (2a) yielded a curved Bronsted-type plot. Similarly, a linear Bronsted-type plot with a β1g value of -0.66 was obtained for the reactions of 1a-j with piperidine, while the corresponding reactions of 2a-i gave a curved Bronsted-type plot. The linear Bronsted-type plots for the reactions of 1a-j have been taken as evidence for a concerted mechanism, while the curved Bronsted-type plots for the reactions of 2a-i have been suggested to indicate a change in the rate-determining step of a stepwise mechanism. The Hammett plot for the reactions of 1b-j exhibited a poor correlation with σ- constants (R2 = 0.962) but slightly better correlation with σo (R2 = 0.986). However, the Yukawa-Tsuno plot for the same reactions resulted in an excellent correlation (R2 = 0.9993) with an r value of 0.30. The aminolysis of 1a-j has been suggested to proceed through a concerted mechanism with an early transition state on the basis of the small βnuc and small r values.

Solvation and Catalysis in Displacement at Phosphorus. Reaction of Imidazole and Benzoate Ion with p-Nitrophenyl and 2,4-Dinitrophenyl Diphenylphosphinates

The reactions of two phosphorus esters, p-nitrophenyl diphenylphosphinate (I) and 2,4-dinitrophenyl diphenylphosphinate (II), have been investigated in acetonitrile containing variable amounts of water.The effectiveness of imidazole and benzoate ion as catalysts has been investigated.Whereas the reaction of imidazole with II is quite rapid, the reaction with I is very slow.However, I reacts predominantly by the rate term k and shows no k term.Nucleophilic catalysis and the existence of an anhydride intermediate have been confirmed with I by observation of the carbonyl region in the infrared: a C=O peak appropriate for an anhydride appears with C6H5CO2(1-) and then disappears if imidazole is added.This correlates with kinetic evidence for an equilibrium with benzoate ion alone but complete reaction if benzoate and imidazole are both present.The reaction of II has been shown to proceed by reversible formation of 1-(diphenylphosphinyl)imidazole as an intermediate.