13597-92-7

Basic information

• Product Name: 2,2,4,4,6,6-hexaamino-2,2,4,4,6,6-hexahydro-1,3,5,2,4,6-triazatriphosphorine
• Synonyms: 2,2,4,4,6,6-hexaamino-2,2,4,4,6,6-hexahydro-1,3,5,2,4,6-triazatriphosphorine;1,3,5,2,4,6-Triazatriphosphorine-2,2,4,4,6,6-hexaamine;2,2,4,4,6,6-Hexaamino-1,3,5,2,4,6-triazatriphosphorine
• CAS NO: 13597-92-7
• Molecular Formula: H₁₂N₉P₃
• Molecular Weight: 231.076863
• EINECS: 237-060-4
• Mol File: 13597-92-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 3.83g/cm³
• Refractive Index: 2.741
• PKA: 0.01±0.50(Predicted)
• CAS DataBase Reference: 2,2,4,4,6,6-hexaamino-2,2,4,4,6,6-hexahydro-1,3,5,2,4,6-triazatriphosphorine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,4,4,6,6-hexaamino-2,2,4,4,6,6-hexahydro-1,3,5,2,4,6-triazatriphosphorine(13597-92-7)
• EPA Substance Registry System: 2,2,4,4,6,6-hexaamino-2,2,4,4,6,6-hexahydro-1,3,5,2,4,6-triazatriphosphorine(13597-92-7)

Safety Data

• Hazardous Substances Data: 13597-92-7(Hazardous Substances Data)

Usage

General Description

2,2,4,4,6,6-hexaamino-2,2,4,4,6,6-hexahydro-1,3,5,2,4,6-triazatriphosphorine, also known as HAPT, is a chemical compound with the molecular formula C6H24N6P3. It is a nitrogen and phosphorus-containing compound that has potential application as a flame retardant. HAPT has been studied for its ability to reduce the flammability and smoke generation of various polymers, making it a promising candidate for use in the construction, transportation, and electronics industries. Additionally, it has been investigated for its potential use in the development of environmentally friendly flame retardants due to its low toxicity and potential for biodegradation. Overall, HAPT shows promise as a novel flame retardant with potential benefits for a range of industries.

InChI:InChI=1/H12N9P3/c1-10(2)7-11(3,4)9-12(5,6)8-10/h1-6H2

Synthetic route

2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine (940-71-6) + ammonia (7664-41-7) → hexaaminocyclotriphosphazene (13597-92-7) + ammonium chloride

Conditions	Yield
In neat (no solvent) direct react. of (PNCl2)3 with a large excess of liquid NH3 under pressure; react. completed after 48 h;;	A 36% B n/a
In neat (no solvent) direct react. of (PNCl2)3 with a large excess of liquid NH3 under pressure; react. completed after 48 h;;	A 36% B n/a
In benzene passing gaseous NH3 in a soln. of (NPCl2)3 in C6H6 for a longer period of time; formation of a mixt. of P3N3(NH2)6 and NH4Cl;;

phosphorus pentachloride (10026-13-8, 874483-75-7) + ammonia (7664-41-7) → hexaaminocyclotriphosphazene (13597-92-7) + ammonium chloride

Conditions	Yield
In chloroform addn. of a soln. of PCl5 in CHCl3 to an excess of liquid NH3 at -50 °C;; extraxtion with liquid NH3;;
In chloroform addn. of a soln. of PCl5 in CHCl3 to an excess of liquid NH3 at -50 °C;; extraxtion with liquid NH3;;

phosphorus pentachloride (10026-13-8, 874483-75-7) + ammonia (7664-41-7) → phospham + hexaaminocyclotriphosphazene (13597-92-7) + P4N12H16 (6954-20-7)

Conditions	Yield
In not given react. of PCl5 with NH3;;

phosphorus pentachloride (10026-13-8, 874483-75-7) + ammonia (7664-41-7) → hexaaminocyclotriphosphazene (13597-92-7) + P4N12H16 (6954-20-7)

Conditions	Yield
In not given react. of PCl5 with NH3; formation of P4N4(NH2)8 and P3N3(NH2)6 as decompn. products of intermediate P(NH2)5;;
In not given react. of PCl5 with NH3; formation of an excess of P3N3(NH2)6, P4N4(NH2)8 and higher polymers as decompn. products of intermediate P(NH2)5;;
In not given react. of PCl5 with NH3; formation of P4N4(NH2)8 and P3N3(NH2)6 as decompn. products of intermediate P(NH2)5;;
In not given react. of PCl5 with NH3; formation of an excess of P3N3(NH2)6, P4N4(NH2)8 and higher polymers as decompn. products of intermediate P(NH2)5;;

2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine (940-71-6) + ammonia (7664-41-7) → hexaaminocyclotriphosphazene (13597-92-7)

hexakis(amino)cyclotriphosphazene hemiammoniate → hexaaminocyclotriphosphazene (13597-92-7)

Conditions	Yield
With KNH2 In ammonia NH3 (liquid); High Pressure; react. of semi ammoniate and KNH2 (molar ratio 1:12), 130°C, 110 bar, 5d;

hexaaminocyclotriphosphazene (13597-92-7) + water (7732-18-5) → P3N6O3H9 (154267-29-5)

Conditions	Yield
In water hydrolysis;;
In water hydrolysis;;

hexaaminocyclotriphosphazene (13597-92-7) → phospham

Conditions	Yield
In neat (no solvent) heating in vac. at 380°C for 100 h;;	>99
In neat (no solvent) heating for a longer period of time;;
In neat (no solvent) heating in vac. at 220°C for several days;;	>99

hexaaminocyclotriphosphazene (13597-92-7) → phospham + ammonia (7664-41-7)

Conditions	Yield
In neat (no solvent) evolution of NH3 on air starting at 125 °C;;
In neat (no solvent) heating; decompn. rate depending on material of the vessel;;
In neat (no solvent) evolution of NH3 on air starting at 125 °C;;
In neat (no solvent) heating in vacuum at 380 °C for 100 h; evolution of NH3 starting in vacuum at 40 °C; evolution of a large amount of NH3 at 200-300 °C; no evolution of NH3 at 400-450 °C;;

hexaaminocyclotriphosphazene (13597-92-7) → phosphoric acid (86119-84-8, 7664-38-2)

Conditions	Yield
With HNO3 or acetic acid; H2O In water hydrolysis with acetic acid or diluted HNO3;;
With H2O In water hydrolysis in the heat;;

hexaaminocyclotriphosphazene (13597-92-7) → ammonium sulfate + ammonium dihydrogen phosphate (7722-76-1)

Conditions	Yield
With H2SO4 In not given react. with H2SO4; formation of a mixture of NH4H2PO4 and (NH4)2SO4 and white vapors of volatile N compounds;;

hexaaminocyclotriphosphazene (13597-92-7) → ammonia (7664-41-7)

Conditions	Yield
With sodium hydroxide In not given heating with an excess of NaOH soln.; evolution of 3 mol NH3/mol P3N3(NH2)6;;
With NaOH In not given heating with an excess of NaOH soln.; evolution of 3 mol NH3/mol P3N3(NH2)6;;

hexaaminocyclotriphosphazene (13597-92-7) + sodium nitrite (7632-00-0) → nitrogen (7727-37-9)

Conditions	Yield
In acetic acid evolution of N2 by react. of NaNO2 with a soln. in abs. glacial acetic acid;;
In acetic acid evolution of N2 by react. of NaNO2 with a soln. in abs. glacial acetic acid;;

hexaaminocyclotriphosphazene (13597-92-7) + mercury(II) diacetate (1600-27-7) → P3N3(NH2)3(NHHgOOCCH3)3

Conditions	Yield
In acetone stirring (6-12 h), Hg:hexaaminocyclotriphosphazene ratio 6-12; washing (acetone), drying in air; elem. anal.;

hexaaminocyclotriphosphazene (13597-92-7) + mercury(II) diacetate (1600-27-7) → P3N3(NH2)5NHHgOOCCH3*0.5CH3COOH

Conditions	Yield
In acetone stirring (6-12 h), Hg:hexaaminocyclotriphosphazene ratio 2-3; washing (acetone), drying in air; elem. anal.;

hexaaminocyclotriphosphazene (13597-92-7) + mercury(II) diacetate (1600-27-7) → (P3N3(NH2)5NH)2Hg*1.5CH3COOH

Conditions	Yield
In acetone stirring (2-28 h) in eqimolar ratio; washing (acetone), drying in air; elem. anal.;

methanol (67-56-1) + hexaaminocyclotriphosphazene (13597-92-7) → PN(NH2)(NHCH3) + PNNH4OH

Conditions	Yield
In not given react. with methanol forming PNNH4OH and PN(NH2)(NHCH3) (molar ratio 3:10);;
In not given react. with methanol forming PNNH4OH and PN(NH2)(NHCH3) (molar ratio 3:10);;

hexaaminocyclotriphosphazene (13597-92-7) → P3N9H12*H2O (27927-18-0)

Conditions	Yield
In water pptn. of aq. P3N3(NH2)6 with the same volume of alcohol or on evaporating at ambient temp.;;

hexaaminocyclotriphosphazene (13597-92-7) + zinc(II) chloride (7646-85-7) → Zn7(P12N24)Cl2 (136952-79-9) + ammonium chloride

Conditions	Yield
In neat (no solvent)

hexaaminocyclotriphosphazene (13597-92-7) + iron(II) chloride → Fe7{P12N24}Cl2 + ammonium chloride

Conditions	Yield
In neat (no solvent)

hexaaminocyclotriphosphazene (13597-92-7) + cobalt(II) chloride (7646-79-9) → Co7{P12N24}Cl2 + ammonium chloride

Conditions	Yield
In neat (no solvent)

hexaaminocyclotriphosphazene (13597-92-7) + cobalt(II) chloride (7646-79-9) → Co5H4{P12N24}Cl2

Conditions	Yield
In neat (no solvent) byproducts: NH4Cl; 24-72 h, 250-750°C; sublimation, boiling (conc. HCl), washing (H2O);

chromium dichloride + hexaaminocyclotriphosphazene (13597-92-7) → Cr7{P12N24}Cl2 + ammonium chloride

Conditions	Yield
In neat (no solvent)

hexaaminocyclotriphosphazene (13597-92-7) + copper dichloride → Cu7{P12N24}Cl2 + ammonium chloride

Conditions	Yield
In neat (no solvent)

hexaaminocyclotriphosphazene (13597-92-7) + nickel dichloride → Ni7{P12N24}Cl2 + ammonium chloride

Conditions	Yield
In neat (no solvent)

hexaaminocyclotriphosphazene (13597-92-7) + lead(II) chloride → Pb7{P12N24}Cl2 + ammonium chloride

Conditions	Yield
In neat (no solvent)

hexaaminocyclotriphosphazene (13597-92-7) + zinc(II) chloride (7646-85-7) → Zn4.8H4.4[P12N24]Cl2

Conditions	Yield
In neat (no solvent) byproducts: NH4Cl; 72 h, 700°C; sublimation, boiling (conc. HCl), washing (H2O);

hexaaminocyclotriphosphazene (13597-92-7) + iron(II) chloride → Fe3.4H6.4P12N24Cl1.2

Conditions	Yield
In neat (no solvent) byproducts: NH4Cl; 72 h, 700°C; sublimation, boiling (conc. HCl), washing (H2O);

Upstream product

• 10026-13-8 phosphorus pentachloride 
• 7664-41-7 ammonia 
• 940-71-6 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine 

Downstream Products

• 86119-84-8 phosphoric acid 
• 7722-76-1 ammonium dihydrogen phosphate 

Relevant articles and documents

X-ray crystal structures and DFT calculations of differently charged aminocyclophosphazenes

Molecular structures of hexakis(amino)cyclotriphosphazene, N3P3(NH2)6, neutral and cationic forms of hexakis(ethylamino)cyclotriphosphazene, N3P3(NHC2H5)6,

Nitrido-Sodalites. II. Synthesis, Crystal Structure, and Properties of M(6+(y/2)-x)H(2x)[P12N24]Z(y) with M=Fe, Co, Ni, Mn; Z=Cl, Br, I; 0<=x<=4; y<=2

The nitrido sodalites M(6+(y/2)-x)H(2x)[P12N24]Z(y) with M=Fe, Co, Ni, Mn; Z=Cl, Br, I; 0=x=4; y=2 are obtained by the reaction of HPN2 or [PN(NH2)2]3 with the metal halogenide MZ2 (T=700°C). The compounds are isotypic to Zn(7-x)H(2x)[P12N24]Cl2. An increase of the ionic radii of the cations or anions results in an expansion of the lattice which iscaused by an increase of the P-N-P angle. The influence of the cation i s more dominant than that of the anion. By reacting [PN(NH2)2]3 with metal halogenide (MZ2) hydrogen free, X-ray amorphous products are obtained. The formation of the chloride-containing P-N sodalite in this reactionbegins at temperatures below 450°C.