6630-15-5

Basic information

• Product Name: Di-p-tolyl Phosphorochloridate
• Synonyms: Di-p-tolyl Phosphorochloridate;1-[chloro-(4-methylphenoxy)phosphoryl]oxy-4-methylbenzene
• CAS NO: 6630-15-5
• Molecular Formula: C₁₄H₁₄ClO₃P
• Molecular Weight: 296.685921
• Product Categories: Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 6630-15-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 399°Cat760mmHg
• Flash Point: 302.1°C
• Appearance: /
• Density: 1.271g/cm³
• Vapor Pressure: 3.26E-06mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: Di-p-tolyl Phosphorochloridate(CAS DataBase Reference)
• NIST Chemistry Reference: Di-p-tolyl Phosphorochloridate(6630-15-5)
• EPA Substance Registry System: Di-p-tolyl Phosphorochloridate(6630-15-5)

Safety Data

• Hazardous Substances Data: 6630-15-5(Hazardous Substances Data)

Usage

Description

Di-p-tolyl Phosphorochloridate is an organophosphorus compound that serves as an intermediate in the synthesis of various chemical compounds. It is characterized by its reactivity and ability to form derivatives, making it a valuable component in the production of specific chemicals.

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 
• 93312-44-8 cyanocarbamimidoyl-phosphoramidic acid di-p-tolyl ester 
• 10359-38-3 Di-(4-methylphenyl)-4-nitrophenylphosphat 
• 21966-23-4 4-aminopyridine 
• 116992-81-5 C₁₄H₁₄Cl₃NO₃P₂ 
• 105077-59-6 N-(di-p-cresylphosphinoyl)-N'-t-butylhydrazine 
• 105094-95-9 N-(di-p-cresylphosphinoyl)hydroxylamine 
• 56830-89-8 di-p-methylphenyl amidophosphate 
• 51169-41-6 Di-p-tolylphosphorohydrazide 
• 843-24-3 bis-(4-methylphenyl)phosphoric acid 
• 115752-39-1 (4-Amino-3-nitro-phenyl)-phosphoramidic acid di-p-tolyl ester 
• 74270-18-1 ethyl bis(4-methylphenyl) phosphate 
• 438017-61-9 C₂₀H₁₉ClNO₃P 
• 75905-89-4 C₂₁H₂₂NO₄P 

Relevant articles and documents

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%).

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.