3848-51-9

Usage

Uses

Used in Plastics and Polymer Industry:
Diphenyl anilinophosphonate is used as a flame retardant and plasticizer for enhancing the fire safety and flexibility of plastics, polymers, and resins. Its incorporation into these materials helps to reduce their flammability, making it an essential additive in the production of electrical equipment, cables, and textiles.
Used in Electrical Equipment Manufacturing:
In the electrical equipment industry, Diphenyl anilinophosphonate is utilized as a flame retardant to ensure that the materials used in the construction of electrical components possess enhanced fire resistance. This contributes to the safety and durability of the equipment.
Used in Cable Production:
For cable production, Diphenyl anilinophosphonate serves as a critical component that improves the fire retardancy of the cables, thereby reducing the risk of fire hazards and ensuring the longevity of the cables in various applications.
Used in Textile Industry:
In the textile industry, Diphenyl anilinophosphonate is employed as a flame retardant to treat fabrics, providing them with fire-resistant properties. This is particularly important for applications where fire safety is a priority, such as in the production of upholstery, carpets, and protective clothing.
Overall, Diphenyl anilinophosphonate's versatility, thermal stability, and resistance to leaching, coupled with its low toxicity and cost-effectiveness, make it a preferred choice for a wide range of applications across different industries.

InChI:InChI=1/C18H16NO3P/c20-23(19-16-10-4-1-5-11-16,21-17-12-6-2-7-13-17)22-18-14-8-3-9-15-18/h1-15H,(H,19,20)

Upstream product

• 101-02-0 triphenyl phosphite 
• 13833-68-6 2,4-dichloro-1,3-diphenyl-cyclodiphosphazane-2,4-dioxide 
• 139-02-6 sodium phenoxide 
• 17436-43-0 phenyl-imidophosphoric acid triphenyl ester 
• 62-53-3 aniline 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 108-95-2 phenol 
• 4712-55-4 diphenyl hydrogen phosphite 
• 70677-19-9 diphenyl phosphorobromidate 
• 5401-14-9 phosphor(isothiocyanatidic) acid diphenyl ester 
• 770-12-7 O-phenyl phosphorodichloridate 
• 26350-10-7 diphenyl phenylphosphoramidite 
• 41399-75-1 2,2-diphenoxy-3-phenyl-4,4-bis-trifluoromethyl-2-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-2λ⁵-[1,3,2]oxazaphosphetidine 
• 6955-57-3 phenylamidophosphoric dichloride 

Downstream Products

• 62-53-3 aniline 
• 108-95-2 phenol 
• 58046-12-1 dimethyl N-phenyl-phosphoramidate 
• 6254-02-0 O-phenyl-N-phenylphosphoramidate 
• 75040-62-9 methyl N-phenylphosphoramidate 
• 100381-33-7 phenyl-amidophosphoric acid methyl ester-phenyl ester 
• 54858-90-1 C₁₂H₁₁NO₃P^(1-)*Na⁽¹⁺⁾ 
• 1445-38-1 diethyl phenylphosphoramidate 
• 63542-04-1 O-ethyl N-phenylphosphoramidic acid 
• 49802-22-4 (4-chloro-phenyl)-amidophosphoric acid diphenyl ester 
• 838-85-7 diphenyl hydrogen phosphate 
• 95220-16-9 Diphenyl-N-chlor-N-phenylphosphoramidat 

Relevant academic research and scientific papers

Kinetics and mechanism of the anilinolysis of aryl phenyl isothiocyanophosphates in acetonitrile

Kinetic studies on the reactions of Y-aryl phenyl isothiocyanophosphates with substituted X-anilines and deuterated X-anilines were carried out in acetonitrile at 55.0 °C. The free-energy relationships with X in the nucleophiles were biphasic concave upwards with a break region between X = H and 4-Cl, giving unusual positive ρX and negative βX values with less basic anilines (X = 4-Cl and 3-Cl). A stepwise mechanism with rate-limiting bond breaking for more basic anilines and with rate-limiting bond formation for less basic anilines is proposed based on the positive and negative ρXY values, respectively. The deuterium kinetic isotope effects involving deuterated anilines (XC6H4ND2) showed primary normal and secondary inverse DKIEs for more basic and less basic anilines, rationalized by frontside attack involving hydrogen-bonded four-center-type TSf and backside attack TSb, respectively. The positive ρX values with less basic anilines are substantiated by the tight TS, in which the extent of the bond formation is great and the degree of the bond breaking is considerably small.

The Step-Wise Synthesis of Oligomeric Phosphoramidates

In this study, the step-wise synthesis to a series of higher phosphoramidates was explored, affording compounds containing N?P?N, symmetric and asymmetric P?N?P and P?N?P?N?P linkages. Salt elimination and lithiation strategies were employed to create the new P?N bonds. It was found that the steric bulk and electronic contribution of the substituents on the P(V) centers were important factors to the success of the reactions. The oligomeric phosphoramidates were characterized by multinuclear NMR and IR spectroscopies as well as ESI mass spectrometry. A selection of the synthesized P?N oligomers were evaluated for their antimicrobial activity against E.coli, S.aureus, C.albicans, and A.fumigatus at varying concentrations. The results suggest their potential use as environmentally friendly fire retardants as the minimal inhibitory concentration (MIC) value for all the compounds was found to be >128 μM, indicating that the compounds do not have any detectable antimicrobial activity.

Synthesis and extraction behavior of alkyl and cyclic aminophosphonates towards actinides

Alkyl and cyclic substituted aminophosphonates (AmPs) were synthesized and characterized with various spectroscopic techniques. The molecular structures of diphenyl phenyl aminophosphonate (DPhPhAmP) and diphenyl cyclohexyl aminophosphonate (DPhCyAmP) wer

Synthesis method of aromatic amide phosphate compound and flame retardant containing compound

The invention discloses a one-pot synthesis method of an aromatic amide phosphate compound. Firstly, phosphorus trioxyhalogen and a monophenol compound or a bisphenol compound react in the presence of a lewis acid catalyst to produce a mono- and/or poly-halogenated phosphate ester compound; secondarily, the mono- and/or poly-halogenated phosphate ester compound and at least one amine compound of a monoamine compound with one primary amino group and/or secondary amino group in molecules and a diamine compound with two primary amino groups and/or secondary amino groups in molecules are subjected to a dehydrohalogenation reaction in the presence of lewis base, and the aromatic amide phosphate compound is produced; finally, the aromatic amide phosphate compound is purified, and a target product is obtained. The one-pot synthesis method has the advantages that with the adoption of one-pot, an intermediate, namely, the mono- and/or poly-halogenated phosphate ester compound, obtained through the reaction is not required to be distilled and/or rectified and purified, required energy consumption is greatly reduced, required production equipment is greatly simplified, corrosive damage of equipment is greatly reduced, the whole process is simple and practical, the production cost is low, the environmental pressure is small, and the product quality is high.

METHOD FOR PRODUCING PHOSPHORIC ACID ESTER AMIDE

PROBLEM TO BE SOLVED: To provide a method for producing phosphoric acid ester amide in which by not using excess aromatic amine with respect to phosphorochloridate, that is, by using aromatic amine by 0.8 to 1.2 equivalents with respect to phosphorochlori

Kinetics and mechanism of the anilinolysis of dibutyl chlorophosphate in acetonitrile

The nucleophilic substitution reactions of dibutyl chlorophosphate (3) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated kinetically in acetonitrile at 55.0 °C. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are secondary inverse (kH/kD = 0.86-0.97) with the strongly basic anilines while primary normal (kH/kD = 1.04-1.10) with the weakly basic anilines. The DKIEs, steric effects of the two ligands, activation parameters, cross-interaction constants, variation trends of the kH/kD values with X, and mechanism are discussed for the anilinolyses of the nine (R1O)(R2O)P(=O)Cl-type chlorophosphates. A concerted mechanism is proposed with a backside nucleophilic attack transition state for the strongly basic anilines and with a frontside attack involving a hydrogen-bonded four-center-type transition state for the weakly basic anilines on the basis of the magnitudes, secondary inverse and primary normal, and variation trends of the kH/kD values with X.

Kinetics and mechanism of the anilinolysis of dibutyl chlorothiophosphate in acetonitrile

The nucleophilic substitution reactions of dibutyl chlorothiophosphate (4S) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated kinetically in acetonitrile at 55.0 °C. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are primary normal (k H/kD = 1.10-1.35). A concerted mechanism involving predominant frontside nucleophilic attack is proposed on the basis of the primary normal DKIEs and selectivity parameters. Hydrogen bonded, four-center-type transition state is proposed. The steric effects of the two ligands on the anilinolysis rates of the chlorothiophosphates are discussed. The anilinolyses of P=S systems are compared with those of their P=O counterparts on the basis of the reactivities, thio effects, selectivity parameters, and DKIEs.

Kinetics and mechanism of anilinolysis of phenyl n-phenyl phosphoramidochloridate in acetonitrile

The kinetic studies on the reactions of phenyl N-phenyl phosphoramidochloridate (8) with substituted anilines (XC6H 4NH2) and deuterated anilines (XC6H 4ND2) have been carried out in acetonitrile at 60.0 oC. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are huge secondary inverse (kH/kD = 0.52-0.69). A concerted mechanism is proposed with a backside attack transition state (TS) on the basis of the secondary inverse DKIEs and the variation trends of the kH/kD values with X. The degree of bond formation in the TS is really extensive taking into account the very small values of the DKIEs. The steric effects of the two ligands on the rates are extensively discussed for the aminolyses of the chlorophosphate-type substrates on the basis of the Taft equation.

Kinetics and mechanism of the anilinolysis of diisopropyl chlorophosphate in acetonitrile

The nucleophilic substitution reactions of diisopropyl chlorophosphate (3) with substituted anilines (XC6H4NH2) and deuterated anilines (XC6H4ND2) are investigated kinetically in acetonitrile at 55.0 oC. The anilinolysis rate of 3 is rather slow to be rationalized by the conventional stereoelectronic effects. The obtained deuterium kinetic isotope effects (DKIEs; kH/kD) are secondary inverse (kH/kD = 0.71-0.95) with maximum magnitude at X = H. A concerted mechanism involving predominant backside nucleophilic attack is proposed on the basis of the secondary inverse DKIEs.

Kinetics and mechanism of the anilinolysis of bis(aryl) chlorophosphates in acetonitrile

The nucleophilic substitution reactions of bis(Y-aryl) chlorophosphates (1) with substituted anilines and deuterated anilines are investigated kinetically in acetonitrile at 35.0 °C. The kinetic results of 1 are compared with those of Y-aryl phenyl chlorophosphates (2). The substrate 1 has one more identical substituent Y compared to substrate 2. The cross-interaction between Y and Y, due to additional substituent Y, is significant enough to result in the change of the sign of cross-interaction constant (CIC) from negative ρXY = -1.31 (2) to positive ρXY = +1.91 (1), indicating the change of reaction mechanism from a concerted SN2 (2) to a stepwise mechanism with a rate-limiting leaving group departure from the intermediate (1). The deuterium kinetic isotope effects (DKIEs) involving deuterated anilines (XC6H4ND2) show secondary inverse, k H/kD = 0.61-0.87. The DKIEs invariably increase as substituent X changes from electron-donating to electron-withdrawing, while invariably decrease as substituent Y changes from electron-donating to electron-withdrawing. A stepwise mechanism with a rate-limiting bond breaking involving a predominant backside attack is proposed on the basis of positive sign of ρXY and secondary inverse DKIEs.