4151-51-3

Basic information

• Product Name: Tris(4-isocyanatophenyl) thiophosphate
• Synonyms: 4-ISOCYANATOPHENOL PHOSPHOROTHIOATE (ESTER));4-isocyanatophenol phosphorothioate (3:1);Thiophosphoric-Tris-p-Isocyanato-Phenyl Ester;Phosphorothioic acid O,O,O-tri(4-isocyanatophenyl) ester;Thiophosphoric acid O,O,O-tri(4-isocyanatophenyl) ester;Thiophosphoric acid O,O,O-tris(4-isocyanatophenyl) ester;Thiophosphoric acid tris(4-isocyanatophenyl) ester;Thiophosphoric acid tris(p-isocyanatophenyl) ester
• CAS NO: 4151-51-3
• Molecular Formula: C₂₁H₁₂N₃O₆PS
• Molecular Weight: 465.38
• EINECS: 223-981-9
• Mol File: 4151-51-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 84-86 °C
• Boiling Point: 561.9 °C at 760 mmHg
• Flash Point: 293.7 °C
• Appearance: /
• Density: 1.37 g/cm³
• Vapor Pressure: 1.18E-12mmHg at 25°C
• Refractive Index: 1.636
• Water Solubility: 150μg/L at 20℃
• CAS DataBase Reference: Tris(4-isocyanatophenyl) thiophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Tris(4-isocyanatophenyl) thiophosphate(4151-51-3)
• EPA Substance Registry System: Tris(4-isocyanatophenyl) thiophosphate(4151-51-3)

Safety Data

• RIDADR: 2206
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 4151-51-3(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C21H12N3O6PS/c25-13-22-16-1-7-19(8-2-16)28-31(32,29-20-9-3-17(4-10-20)23-14-26)30-21-11-5-18(6-12-21)24-15-27/h1-12H

Synthetic route

tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + dimethyl amine (124-40-3) → tri[p-(dimethylcarbamoylamino)phenyl]thiophosphate

Conditions	Yield
In ethyl acetate; toluene at 20 - 25℃; for 1.5h;	100%

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) → C39H42N3O15PS

Conditions	Yield
With stannous octoate In ethyl acetate at 60℃; for 16h;	94.5%

tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + β-naphthol (135-19-3) + 2-hydroxyethyl acrylate (818-61-1) → C46H36N3O11PS

Conditions	Yield
Stage #1: tris(p-isocyanatophenyl)phosphorothioate; 2-hydroxyethyl acrylate In acetic acid butyl ester at 50℃; for 2h; Reflux; Stage #2: β-naphthol In acetic acid butyl ester	93%

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + phenol (108-95-2) → C39H34N3O11PS

Conditions	Yield
Stage #1: 2-methyl-2-propenoic acid 2-hydroxyethyl ester; tris(p-isocyanatophenyl)phosphorothioate In acetic acid butyl ester at 50℃; for 2h; Reflux; Stage #2: phenol In acetic acid butyl ester	89%

4-Phenylphenol (92-69-3) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + 2-hydroxyethyl acrylate (818-61-1) → C50H40N3O11PS

Conditions	Yield
Stage #1: tris(p-isocyanatophenyl)phosphorothioate; 2-hydroxyethyl acrylate In acetic acid butyl ester at 50℃; for 2h; Reflux; Stage #2: 4-Phenylphenol In acetic acid butyl ester	88%

2-hydroxy-1,3-bis(phenylthio)propane (22910-07-2) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + 2-hydroxyethyl acrylate (818-61-1) → C56H52N3O11PS5

Conditions	Yield
Stage #1: 2-hydroxy-1,3-bis(phenylthio)propane; tris(p-isocyanatophenyl)phosphorothioate With stannous octoate In ethyl acetate at 60℃; for 4h; Stage #2: 2-hydroxyethyl acrylate In ethyl acetate at 60℃; for 16h;	84%

ortho-mercaptophenol (1121-24-0) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) → C38H32N3O9PS3

Conditions	Yield
Stage #1: tris(p-isocyanatophenyl)phosphorothioate With 2-hydroxyethyl acrylate In acetic acid butyl ester at 50℃; for 2h; Reflux; Stage #2: ortho-mercaptophenol In acetic acid butyl ester	83%

tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + phenol (108-95-2) + 2-hydroxyethyl acrylate (818-61-1) → C38H32N3O11PS

Conditions	Yield
Stage #1: tris(p-isocyanatophenyl)phosphorothioate; 2-hydroxyethyl acrylate In acetic acid butyl ester at 50℃; for 2h; Stage #2: phenol In acetic acid butyl ester	83%

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + 2-hydroxyethyl acrylate (818-61-1) → C38H40N3O15PS

Conditions	Yield
Stage #1: tris(p-isocyanatophenyl)phosphorothioate; 2-hydroxyethyl acrylate With stannous octoate In ethyl acetate at 60℃; for 2h; Stage #2: 2-methyl-2-propenoic acid 2-hydroxyethyl ester In ethyl acetate at 60℃; for 16h;	80%

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + 2-hydroxy-1,3-bis(phenylthio)propane (22910-07-2) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) → C48H48N3O13PS3

Conditions	Yield
Stage #1: 2-hydroxy-1,3-bis(phenylthio)propane; tris(p-isocyanatophenyl)phosphorothioate With stannous octoate In ethyl acetate at 60℃; for 3h; Stage #2: 2-methyl-2-propenoic acid 2-hydroxyethyl ester In ethyl acetate at 60℃; for 16h;	75%

tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + 2-hydroxyethyl acrylate (818-61-1) → phosphorothioyltris(oxy-4,1-phenyleneiminocarbonyloxyethane-2,1-diyl)triacrylate

Conditions	Yield
With stannous octoate In ethyl acetate at 60℃; for 16h;	73%
With 2,6-di-tert-butyl-4-methyl-phenol; dibutyltin dilaurate In ethyl acetate at 60℃;
With 2,6-di-tert-butyl-4-methyl-phenol at 60℃;

2-hydroxy-1,3-bis(phenylthio)propane (22910-07-2) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + 2-hydroxyethyl acrylate (818-61-1) → C46H44N3O13PS3

Conditions	Yield
Stage #1: 2-hydroxy-1,3-bis(phenylthio)propane; tris(p-isocyanatophenyl)phosphorothioate In ethyl acetate at 60℃; for 2h; Stage #2: 2-hydroxyethyl acrylate In ethyl acetate at 60℃; for 16h;	73%

tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + allyl alcohol (107-18-6) → C30H30N3O9PS

Conditions	Yield
With stannous octoate In ethyl acetate at 60℃; for 16h;	31%

2,2,2-trifluoroethanol (75-89-8) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + 2-hydroxyethyl acrylate (818-61-1) → [(4-{[(2,2,2-trifluoroethoxy)carbonyl]amino}phenoxy)thiophosphoryl]bis(oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl)diacrylate

Conditions	Yield
Stage #1: 2,2,2-trifluoroethanol; tris(p-isocyanatophenyl)phosphorothioate With 2,6-di-tert-butyl-4-methyl-phenol; dibutyltin dilaurate In ethyl acetate at 60℃; for 8h; Stage #2: 2-hydroxyethyl acrylate In ethyl acetate at 60℃;

2,2,2-trifluoroethanol (75-89-8) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + 2-hydroxyethyl acrylate (818-61-1) → 2-{[(4-{[bis(4-{[(2,2,2-trifluoroethoxy)carbonyl]amino}phenoxy)thiophosphoryl]oxy}phenyl)carbamoyl]oxy}ethyl acrylate

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; dibutyltin dilaurate In ethyl acetate at 60℃;

2,2,2-trifluoroethanol (75-89-8) + 2-hydroxybutyl acrylate (2421-27-4) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) → [(4-{[(2,2,2-trifluoroethoxy)carbonyl]amino}phenoxy)thiophosphoryl]bis(oxybenzene-4,1-diylcarbamoyloxybutane-4,1-diyl)diacrylate

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; dibutyltin dilaurate In ethyl acetate at 60℃;

1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + 2-hydroxyethyl acrylate (818-61-1) → {[4-({[(1,1,1,3,3,3-hexafluoropropan-2-yl)oxy]carbonyl}amino)phenoxy]thiophosphoryl}bis(oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl)diacrylate

Conditions	Yield
Stage #1: 1,1,1,3',3',3'-hexafluoro-propanol; tris(p-isocyanatophenyl)phosphorothioate With 2,6-di-tert-butyl-4-methyl-phenol; dibutyltin dilaurate In ethyl acetate at 60℃; for 8h; Stage #2: 2-hydroxyethyl acrylate In ethyl acetate at 60℃;

2-hydroxybutyl acrylate (2421-27-4) + 1,1,1,3',3',3'-hexafluoro-propanol (920-66-1) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) → {[4-({[(1,1,1,3,3,3-hexafluoropropan-2-yl)oxy]carbonyl}amino)phenoxy]thiophosphoryl}bis(oxybenzene-4,1-diylcarbamoyloxybutane-4,1-diyl)diacrylate

Conditions	Yield
Stage #1: 1,1,1,3',3',3'-hexafluoro-propanol; tris(p-isocyanatophenyl)phosphorothioate With 2,6-di-tert-butyl-4-methyl-phenol; dibutyltin dilaurate In ethyl acetate at 60℃; for 8h; Stage #2: 2-hydroxybutyl acrylate In ethyl acetate at 60℃;

tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + 2-hydroxyethyl acrylate (818-61-1) → phosphorothioyltris(oxybenzene-4,1-diylcarbamoyloxyethane-2,1-diyl)trisacrylate

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; dibutyltin dilaurate In ethyl acetate at 60℃;

2-methyl-2-propenoic acid 2-hydroxyethyl ester (868-77-9) + tris(p-isocyanatophenyl)phosphorothioate (4151-51-3) + thiophenol (108-98-5) → C39H34N3O9PS3

Conditions	Yield
Stage #1: tris(p-isocyanatophenyl)phosphorothioate; thiophenol With stannous octoate In ethyl acetate at 60℃; for 3h; Stage #2: 2-methyl-2-propenoic acid 2-hydroxyethyl ester In ethyl acetate at 60℃; for 16h;