7450-69-3

Basic information

• Product Name: PHENYLPHOSPHORODIAMIDATE
• Synonyms: PHENYLPHOSPHORODIAMIDATE;phenyl diamidophosphate;Phosphoric acid phenyl ester diamide;Phenyl phosphorodiamidate, 98+%;phosphoric phenyl ester diamide;Diamidophosphoric acid phenyl ester;Phosphorodiamidic acid phenyl ester;Phenyl phosphorodiamidate,97%
• CAS NO: 7450-69-3
• Molecular Formula: C₆H₉N₂O₂P
• Molecular Weight: 172.12
• EINECS: 231-218-6
• Mol File: 7450-69-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 183-185 °C
• Boiling Point: 313.8ºC at 760 mmHg
• Flash Point: 143.6ºC
• Appearance: White to gray/Powder and Flakes
• Density: 1.34g/cm3
• Vapor Pressure: 0.000487mmHg at 25°C
• Refractive Index: 1.571
• PKA: 1.41±0.70(Predicted)
• Water Solubility: 5.6g/L at 20℃
• Sensitive: Air & Light Sensitive
• BRN: 608629
• CAS DataBase Reference: PHENYLPHOSPHORODIAMIDATE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLPHOSPHORODIAMIDATE(7450-69-3)
• EPA Substance Registry System: PHENYLPHOSPHORODIAMIDATE(7450-69-3)

Safety Data

• Statements: 25-36/37/38
• Safety Statements: 24/25
• RIDADR: 3278
• PackingGroup: III
• Hazardous Substances Data: 7450-69-3(Hazardous Substances Data)

Usage

Chemical Properties

white to grey powder and flakes

Uses

Reagent for conversion of tautomeric keto-hydroxy groups (e.g. in N-heterocycles) directly to amino groups.

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

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

Downstream Products

• 108-95-2 phenol 
• 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 
• 64402-71-7 2-Phenyloxy-4,6-dioxo-hexahydro-1,3,2-diazphosphorin-2-oxid 
• 22457-53-0 Diamidophosphorsaeuremethylester 
• 18081-61-3 N,N'-Bis-trimethylsilyl-diamidophosphorsaeure-phenylester 

Relevant articles and documents

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.

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.

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.