52664-35-4

Basic information

• Product Name: TRIS-(4-AMINOPHENYL)THIOPHOSPHATE
• Synonyms: Phenol,4-amino-,phosphorothioate(3:1)ester;TRIS-(4-AMINOPHENYL)THIOPHOSPHATE;Tris-(4-aminophenyl)-phosphorothioate;Thiophosphoric acid=O,O,O-tris(p-aminophenyl) ester;Tris(4-Amino Phenyl)thiophos;Einecs 258-083-6;Thionophosphoric acid- tris-( p-aMinophenyl ester )TPTA;O,O,O-tris(4-aMinophenyl) phosphorothioate
• CAS NO: 52664-35-4
• Molecular Formula: C₁₈H₁₈N₃O₃PS
• Molecular Weight: 387.39
• EINECS: 258-083-6
• Mol File: 52664-35-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 156℃
• Boiling Point: 597.922 °C at 760 mmHg
• Flash Point: 315.412 °C
• Appearance: /
• Density: 1.421
• Vapor Pressure: 2.93E-14mmHg at 25°C
• Refractive Index: 1.719
• PKA: 4.37±0.10(Predicted)
• CAS DataBase Reference: TRIS-(4-AMINOPHENYL)THIOPHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS-(4-AMINOPHENYL)THIOPHOSPHATE(52664-35-4)
• EPA Substance Registry System: TRIS-(4-AMINOPHENYL)THIOPHOSPHATE(52664-35-4)

Safety Data

• Hazardous Substances Data: 52664-35-4(Hazardous Substances Data)

Usage

General Description

TRIS-(4-AMINOPHENYL)THIOPHOSPHATE is a chemical compound that consists of a trisubstituted phosphorothioate with three 4-aminophenyl groups attached to the phosphorus atom. It is used in various industrial processes, including as a flame retardant in polymers, especially in polyurethane foam. The compound is also utilized in the production of adhesives and sealants, as well as in the synthesis of pharmaceuticals and agrochemicals. TRIS-(4-AMINOPHENYL)THIOPHOSPHATE is a highly versatile chemical that has applications in several industries due to its flame retardant properties and its ability to enhance the performance of various materials.

InChI:InChI=1/C18H18N3O3PS/c19-13-1-7-16(8-2-13)22-25(26,23-17-9-3-14(20)4-10-17)24-18-11-5-15(21)6-12-18/h1-12H,19-21H2

Synthetic route

tris(N-boc-4-aminophenyl)thiophosphate → tris(4-aminophenyl) thiophosphate (52664-35-4)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 4h;	88%

4-amino-phenol (123-30-8) → tris(4-aminophenyl) thiophosphate (52664-35-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrahydrofuran / 30 h 2: triethylamine; phosphorus trichloride / toluene / 24 h / 0 - 20 °C / Inert atmosphere 3: sulfur / 30 h / Inert atmosphere; Reflux 4: trifluoroacetic acid / dichloromethane / 4 h View Scheme

C33H42N3O9P → tris(4-aminophenyl) thiophosphate (52664-35-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfur / 30 h / Inert atmosphere; Reflux 2: trifluoroacetic acid / dichloromethane / 4 h View Scheme

4-N-tert-butoxycarbonylaminophenol (54840-15-2) → tris(4-aminophenyl) thiophosphate (52664-35-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; phosphorus trichloride / toluene / 24 h / 0 - 20 °C / Inert atmosphere 2: sulfur / 30 h / Inert atmosphere; Reflux 3: trifluoroacetic acid / dichloromethane / 4 h View Scheme

tris(4-acetamidophenyl) thiophosphate (75144-41-1) → tris(4-aminophenyl) thiophosphate (52664-35-4)

Conditions	Yield
With hydrogenchloride In dichloromethane at 45 - 85℃; for 6h;

pyridine-2-carbaldehyde (1121-60-4) + iron(II) tetrafluoroborate + tris(4-aminophenyl) thiophosphate (52664-35-4) → 4Fe(2+)*8BF4(1-)*4C36H27N6O3PS

Conditions	Yield
In acetonitrile for 24h;

cobalt(II) tetrafluoroborate + pyridine-2-carbaldehyde (1121-60-4) + tris(4-aminophenyl) thiophosphate (52664-35-4) → 8BF4(1-)*4C36H27N6O3PS*4Co(2+)

Conditions	Yield
In acetonitrile for 24h;

Upstream product

• 75144-41-1 Tris (4-acetylaminophenyl) Thiophosphate 
• 54840-15-2 4-N-tert-butoxycarbonylaminophenol 
• 123-30-8 4-amino-phenol 

Relevant articles and documents

Preparation method of thiophosphoric acid tri (4-aminobenzene) ester

The invention relates to a preparation method of thiophosphoric acid tri (4-aminobenzene) ester. Specifically, according to the preparation method of the thiophosphoric acid tris (4-aminobenzene) ester, acetaminophen and thiophosphoryl chloride are used as raw materials, and esterification and hydrolysis reactions are performed in sequence to obtain the thiophosphoric acid tris (4-aminobenzene) ester. The synthesis method of thiophosphate tri (4-aminobenzene) ester has the advantages of short synthesis route, simple process operation, mild reaction conditions, short reaction time, fast reaction speed, strong selectivity, high yield, high purity, low cost, avoidance of expensive and highly toxic reagents and catalysts, environmental protection and easy industrial production.