6630-15-5

Usage

Uses

Used in Chemical Synthesis:
Di-p-tolyl Phosphorochloridate is used as an intermediate for the synthesis of Di-p-tolyl-phosphate (D494570), which is a metabolite of tri-p-cresyl phosphate. Tri-p-cresyl phosphate is a flame retardant plasticizer, and its metabolite, Di-p-tolyl-phosphate, plays a role in understanding the degradation and environmental impact of this plasticizer.
Used in Flame Retardant Industry:
Di-p-tolyl Phosphorochloridate is used as a chemical intermediate for the production of flame retardant additives. These additives are crucial in the manufacturing of plastics, textiles, and other materials that require fire-resistant properties. Di-p-tolyl Phosphorochloridate contributes to the development of safer and more effective flame retardants, which can help reduce the risk of fire and protect lives and property.

InChI:InChI=1/C14H14ClO3P/c1-11-3-7-13(8-4-11)17-19(15,16)18-14-9-5-12(2)6-10-14/h3-10H,1-2H3

Upstream product

• 106-44-5 p-cresol 

Downstream Products

• 70138-27-1 bis(4-methylphenyl)phosphinanilide 
• 1207716-82-2 C₂₄H₂₄N₃O₃P 
• 438017-61-9 C₂₀H₁₉ClNO₃P 
• 75905-89-4 C₂₁H₂₂NO₄P 
• 413590-33-7 C₂₀H₁₉ClNO₃P 
• 130896-11-6 p-tolyl-amidephosphoric acid di-p-tolyl ester 
• 105077-59-6 N-(di-p-cresylphosphinoyl)-N'-t-butylhydrazine 
• 115752-28-8 [5-(Bis-p-tolyloxy-phosphorylamino)-1H-benzoimidazol-2-yl]-carbamic acid methyl ester 
• 77394-59-3 N'-[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-phosphorohydrazidic acid di-p-tolyl ester 
• 77394-58-2 N'-[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-phosphorohydrazidic acid di-p-tolyl ester 
• 77394-67-3 N'-[1-Methyl-3-oxo-3-phenyl-prop-(Z)-ylidene]-phosphorohydrazidic acid di-p-tolyl ester 
• 77394-68-4 3-[(Bis-p-tolyloxy-phosphoryl)-hydrazono]-butyric acid ethyl ester 
• 77394-62-8 N'-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-phosphorohydrazidic acid di-p-tolyl ester 

Relevant academic research and scientific papers

Zinc-catalyzed transformation of diarylphosphoryl azides to diarylphosphate esters and amides

We have developed a facile and efficient procedure for the synthesis of diarylphosphate esters and amides. Using Zn(acac)2 as the catalyst, the reaction of diarylphosphoryl azides with aliphatic alcohols and phenols through an unusual P?N bond cleavage provided a number of diarylphosphate esters in good yields (22 examples, up to 94%). Additionally, various diarylphosphate amides were obtained from the corresponding amines in excellent yields as well (8 examples, up to 96%).

Neodymium tris-diarylphosphates: Systematic study of the structure-reactivity relationship in butadiene and isoprene polymerisation

The catalytic properties of neodymium tris-phosphates with various diarylphosphate ligands in the stereoregular 1,4-cis-polymerisation of butadiene and isoprene were studied. The considerable variability of the diaryl phosphate structure allowed for the systematic investigation of the dependence of the catalytic properties of neodymium tris-diarylphosphates on the electronic and steric properties of the ligand. Electron-withdrawing substituents (F, Cl, Br) in the aryl moiety increased the catalyst activity of tris-diarylphosphate. Neodymium aryl phosphates containing lipophilic bulky ligands provided the synthesis of polydienes with a monomodal molecular-weight distribution. The optimal catalytic properties demonstrated that the neodymium aryl phosphate prepared from bis(2,6-dimethyl-4-tert-butylphenyl)-phosphoric acid showed high activity and ensured a monomodal MWD of polydienes (Mw/Mn ～ 2 for polybutadiene and Mw/Mn ～ 3 for polyisoprene) in various conditions.

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.

Metalation-Induced Double Migration of Phosphorus from O-->C. Convenient Preparation of Bis(2-hydroxyaryl)phosphinic Acids

Treatment of diaryl ethyl phosphates 8 with lithium diisopropylamide in tetrahydrofuran yields ethyl bis(2-hydroxyaryl)phosphinates 9.The reaction involves the double migration of phophorus from O-->C and is probably intramolecular.These phosphinate esters 9 on treatment with trimethylsilyl chloride and sodium iodide in acetonitrile undergo transesterification to give trimethylsilyl esters that yield the corresponding phosphinic acids 15 on treatment with water.

CATALYTIC EFFECT OF SUBSTITUTED DIPHENYLPHOSPHORIC ACIDS ON THE FORMATION OF ESTERS

The catalytic effect of substituted diphenylphosphoric acids on the rate of the reaction of butyryl chloride with 1-butanol in toluene was investigated.It was shown that the effect of the nature of the substituent in the acid molecule has little effect on its catalytic activity.This indicates a bifunctional mechanism of catalysis in the reaction.

Preparation of esters of phosphorus acids

Esters of phosphorus acids are prepared by an improved process whereby aromatic alcohols and phosphorus halides are reacted at specified temperatures in the presence of amine catalysts thereby providing high yields of substantially pure esters and allowing preparation of selected halogen-containing mono- and di-esters of phosphorus acids wherein halogen is directly bonded to phosphorus having substantially no side reactant contamination. The phosphorus esters are useful as intermediates in the preparation of plasticizers, oil additives and functional fluids.