7450-69-3

Usage

Uses

Used in Pharmaceutical Industry:
PHENYLPHOSPHORODIAMIDATE is used as a reagent for the conversion of tautomeric keto-hydroxy groups to amino groups, which is essential in the synthesis of various pharmaceutical compounds. This conversion process aids in the development of new drugs and the modification of existing ones to improve their efficacy and safety.
Used in Chemical Research:
In the field of chemical research, PHENYLPHOSPHORODIAMIDATE is utilized as a reagent to facilitate the conversion of specific functional groups in organic molecules. This property is crucial for the synthesis of complex molecules and the exploration of new chemical reactions and mechanisms.
Used in Material Science:
PHENYLPHOSPHORODIAMIDATE may also find applications in material science, particularly in the development of novel materials with specific properties. The ability to convert keto-hydroxy groups to amino groups can be exploited to create materials with tailored characteristics, such as improved stability, reactivity, or selectivity.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C6H9N2O2P/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H,(H4,7,8,9)

Synthetic route

O-phenyl phosphorodichloridate (770-12-7) → phenyl diamidophosphate (7450-69-3)

Conditions	Yield
With ammonium hydroxide at -10℃; for 2.5h;	90%
With ammonia In water at 5 - 20℃;	88%
With ammonia In dichloromethane for 0.166667h;	17.4%

phenol (108-95-2) → diphenylphosphoroamidate (2015-56-7) + phenyl diamidophosphate (7450-69-3)

Conditions	Yield
With pyridine; chloroform; trichlorophosphate at -2℃; Eintragen des Reaktionsgemisches in fluessiges NH3;

phenyl diamidophosphate (7450-69-3) + sodium hydroxide (1310-73-2) → sodium phosphorodiamidate pentahydrate

Conditions	Yield
In sodium hydroxide boiling phenyl ester for 5 min in 4 M NaOH; cooling, addn. of EtOH, pptn., recrystn. (H2O-EtOH), drying (air, room temp.); elem. anal.;	80%

phenyl diamidophosphate (7450-69-3) + malonoyl dichloride (1663-67-8) → 2-Phenyloxy-4,6-dioxo-hexahydro-1,3,2-diazphosphorin-2-oxid (64402-71-7)

Conditions	Yield
In diethyl ether 1.) R.T., 3 h, 2.) reflux, 1 h;	17%

formaldehyd (50-00-0) + phenyl diamidophosphate (7450-69-3) → C7H11N2O3P (61578-57-2)

Conditions	Yield
With sodium hydroxide In isopropyl alcohol

methyltrimethylsilylamine (16513-17-0) + phenyl diamidophosphate (7450-69-3) → N,N'-Bis-trimethylsilyl-diamidophosphorsaeure-phenylester (18081-61-3)

Conditions	Yield
In diethyl ether

phenyl diamidophosphate (7450-69-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → N,N'-Bis-trimethylsilyl-diamidophosphorsaeure-phenylester (18081-61-3)

methanol (67-56-1) + phenyl diamidophosphate (7450-69-3) → Diamidophosphorsaeuremethylester (22457-53-0) + phenol (108-95-2)

Conditions	Yield
With water; manganese(ll) chloride at 25℃; methanolysis, also without H2O;

phenyl diamidophosphate (7450-69-3) → phenol (108-95-2)

Conditions	Yield
In water at 30℃; libratation from carboxymethylcellulose and hydrolysis;

phenyl diamidophosphate (7450-69-3) + alkali → phenol (108-95-2) + phosphoric acid diamide

methanolic ammonia + 1-(2-methoxyphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo<3,2-c>quinoline (122456-32-0) + phenyl diamidophosphate (7450-69-3) → 1-(2-methoxyphenyl)-4-amino-6-methoxy-2,3-dihydropyrrolo<3,2-c>quinoline (122456-35-3)

Conditions	Yield
With sodium hydroxide In dichloromethane

methanolic ammonia + 1-(2-methylphenyl)-4-oxo-6-methyl-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline (122456-57-9) + phenyl diamidophosphate (7450-69-3) → 1-(2-methylphenyl)-4-amino-6-methyl-2,3-dihydropyrrolo<3,2-c>quinoline (122456-38-6)

Conditions	Yield
With sodium hydroxide In dichloromethane

6-METHYL-5-PHENYL-2(1H)-PYRIDONE + phenyl diamidophosphate (7450-69-3) → 6-methyl-5-phenylpyridin-2-amine (84596-30-5)

Conditions	Yield
In diphenylether

phenyl diamidophosphate (7450-69-3) → diamidophosphoric acid (10043-91-1, 25757-55-5) + cyclohexane (110-82-7)

Conditions	Yield
In ethanol catalytic hydrogenation of diamidophosphoric acid phenylester in methanol;;
In ethanol catalytic hydrogenation of diamidophosphoric acid phenylester in methanol;;

phenyl diamidophosphate (7450-69-3) + potassium hydroxide → diamidophosphoric acid (10043-91-1, 25757-55-5)

Conditions	Yield
In water addn. of 30 g (C6H5O)PO(NH2)2 to a hot soln. of 30 g KOH in 30 ml H2O; standing for 5 min; cooling with ice and addn. of a mixt. of 30 g glacial acetic acid and 10 ml H2O then 300 ml ethanol;; pptn. of POOH(NH2)2, washing with alc. and ether, drying on air; dissolving in H2O, pptn. with ethanol;;
In water addn. of 30 g (C6H5O)PO(NH2)2 to a hot soln. of 30 g KOH in 30 ml H2O; standing for 5 min; cooling with ice and addn. of a mixt. of 30 g glacial acetic acid and 10 ml H2O then 300 ml ethanol;; pptn. of POOH(NH2)2, washing with alc. and ether, drying on air; dissolving in H2O, pptn. with ethanol;;

water (7732-18-5) + phenyl diamidophosphate (7450-69-3) + sodium hydroxide (1310-73-2) → sodium diamido phosphate 6-hydrate

Conditions	Yield
In water boiling 34.4g phenyl ester and 16g NaOH in 70ml H2O for 10min, cooling to 0°C, addn. of 200ml ice-cooled methanol;; dissolving in a small amount of H2O, pptn. with ethanol, washing with ethanol and ether,. drying in the air;;
In water boiling 34.4g phenyl ester and 16g NaOH in 70ml H2O for 10min, cooling to 0°C, addn. of 200ml ice-cooled methanol;; dissolving in a small amount of H2O, pptn. with ethanol, washing with ethanol and ether,. drying in the air;;

barium hydroxide octahydrate + phenyl diamidophosphate (7450-69-3) → barium diamidophosphate

Conditions	Yield
In water 15 min boiling in water, cooling under CO2; evapn.;
In water 15 min boiling in water, cooling under CO2; evapn.;

silver nitrate + phenyl diamidophosphate (7450-69-3) → silver diamido phosphate (15122-50-6)

Conditions	Yield
In not given recrystallization from NH3 soln. with nitric acid; very pure;;
In not given recrystallization from NH3 soln. with nitric acid; very pure;;
In not given recrystallization from NH3 soln. with nitric acid; very pure;;

Upstream product

• 770-12-7 O-phenyl phosphorodichloridate 
• 108-95-2 phenol 

Downstream Products

• 18081-61-3 N,N'-Bis-trimethylsilyl-diamidophosphorsaeure-phenylester 
• 22457-53-0 Diamidophosphorsaeuremethylester 
• 108-95-2 phenol 
• 64402-71-7 2-Phenyloxy-4,6-dioxo-hexahydro-1,3,2-diazphosphorin-2-oxid 
• 84596-30-5 6-methyl-5-phenylpyridin-2-amine 
• 10043-91-1 diamidophosphoric acid 
• 110-82-7 cyclohexane 
• 122456-38-6 1-(2-methylphenyl)-4-amino-6-methyl-2,3-dihydropyrrolo<3,2-c>quinoline 
• 122456-35-3 1-(2-methoxyphenyl)-4-amino-6-methoxy-2,3-dihydropyrrolo<3,2-c>quinoline 

Relevant academic research and scientific papers

Bicyclo-imidazoline laurate, synthesis method therefor and application of bicyclo-imidazoline laurate

The invention discloses bicyclo-imidazoline laurate. The bicyclo-imidazoline laurate has a symmetrical molecular structure, comprises two imidazoline heterocycles and two alkyl long chains of lauric acid, and thus, plenty and dense electronic clouds and good hydrophobicity can be provided. The invention further discloses a bicyclo-imidazoline laurate synthesis method, which is low in raw materialcost and high in reaction yield and can achieve industrial production. The invention further discloses an application of the bicyclo-imidazoline laurate. The electrotransport type cationic bicyclo-imidazoline laurate is obtained through activating bicyclo-imidazoline laurate and is applied to the rusting prevention of reinforced concrete.

Synthesis and thermal degradation behaviours of novel phosphorus-containing polyurethane elastomers

Phenyl diaminophosphate was synthesized based on phenyl dichlorophosphate and characterized by Fourier transform infrared spectroscopy and nuclear magnetic resonance. Phenyl diaminophosphate was used as chain extender to prepare a series of phosphorus containing polyurethane elastomers (PPUEs) with different phosphorus contents by changing the soft segments. The thermogravimetric analyses result reveal that the char yield of PPUEs is much higher: the char yield of PPUE1 reaches 35 % whose phosphorus content is just 1.5 %, indicating that the phosphorus contributes to the improved char-forming ability. The microscale combustion colorimeter (MCC) result shows that the PPUEs show better flame retardancy and the flame retardant of the polyurethane elastomer increases with the phosphorus content increasing. The degradation kinetics studies show that the degradation of polyurethane elastomers is divided into two stages, where the activation energy of PPUEs in their first stage is lower than that of corresponding polyurethane elastomers based on 3,3'-dichloro-4,4'-diaminodiphenylmethane (MOCA), but the activation energy in the second stage is higher.

Design, synthesis, and biological evaluation of phosphoramide derivatives as urease inhibitors

The design, synthesis, and biological evaluation of phosphoramide derivatives as urease inhibitors to reduce the loss of ammonia has been carried out. Forty phosphorus derivatives were synthesized and their inhibitory activities evaluated against that of jack bean urease. In addition, in vivo assays have been carried out. All of the compounds were characterized by IR, 1H NMR, MS, and elemental microanalysis. In some cases, detailed molecular modeling studies were carried out, and these highlighted the interaction between the enzyme active center and the compounds and also the characteristics related to their activity as urease inhibitors. According to the IC50 values for in vitro inhibitory activity, 12 compounds showed values below 1 μM and 8 of them represent improvements of activity in comparison to the commercial urease inhibitor N-n-butylthiophosphorictriamide (NBPT) (100 nM) (AGROTAIN). On the basis of the activity results and the conclusions of the molecular modeling study, a structural model for new potential inhibitors has been defined.

ALKALINE SOLVOLYSIS OF DIAMIDOPHOSPHATES

Mechanism of alkaline solvolysis of phenyl diamidophosphates is discussed on the basis of its selectivity, activation entropy and steric effects.All methods used show that the reaction proceeds by SN2 mechanism via an intermediate, containing a pentavalent phosphorus.

Synthesis of Phenyl Phosphorodiamidates

Two procedures are described for the synthesis of phenyl phosphorodiamidates in high yields.These compounds can be represented by the general formula 6 and are used for cyclisation reactions leading to phosphabarbituric acids.