59377-19-4

Basic information

• Product Name: 4-PHENOXYPHENYL ISOCYANATE
• Synonyms: 4-PHENOXYPHENYL ISOCYANATE;4-Isocyanatodiphenyl ether;Benzene, 1-isocyanato-4-phenoxy- (9CI);4-Phenoxyphenyl isocyanate,98%;Benzene, 1-isocyanato-4-phenoxy-;1-isocyanato-4-phenoxybenzene;4-Phenoxyphenyl isocyanate, 98% 1GR;4-Phenoxyphenyl isocyanate, 98% 5GR
• CAS NO: 59377-19-4
• Molecular Formula: C₁₃H₉NO₂
• Molecular Weight: 211.22
• Product Categories: ISOCYANATE;Isocyanates;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 59377-19-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 170 °C3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to slightly yellow liquid
• Density: 1.169 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000725mmHg at 25°C
• Refractive Index: n20/D 1.595(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Sensitive: Moisture Sensitive
• BRN: 393196
• CAS DataBase Reference: 4-PHENOXYPHENYL ISOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENOXYPHENYL ISOCYANATE(59377-19-4)
• EPA Substance Registry System: 4-PHENOXYPHENYL ISOCYANATE(59377-19-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2206 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 59377-19-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

4-Phenoxyphenyl Isocyanate is a reagent used for the preparation of piperazinylquinazoline ureas by condensation of piperazinylquinazoline with aryl isocyanates. It is also reported to be used for the synthesis and evaluation of urea-based indazoles.

General Description

4-Phenoxyphenyl isocyanate, also known as 1-isocyanato-4-phenoxybenzene, is an aryl isocyanate. Its enthalpy of vaporization at boiling point has been reported.

InChI:InChI=1/C13H9NO2/c15-10-14-11-6-8-13(9-7-11)16-12-4-2-1-3-5-12/h1-9H

Synthetic route

phosgene (75-44-5) + 4-phenoxyanilin (139-59-3) → p-phenoxyphenylisocyanate (59377-19-4)

4-phenoxyanilin (139-59-3) + trichloromethyl chloroformate (503-38-8) → p-phenoxyphenylisocyanate (59377-19-4)

Conditions	Yield
With pyrographite In ethyl acetate for 5h; Heating;

4-Phenoxybenzoic acid (2215-77-2) → p-phenoxyphenylisocyanate (59377-19-4)

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In toluene at 20 - 105℃; for 1.16667h; Curtius rearrangement; Inert atmosphere;

bis(trichloromethyl) carbonate (32315-10-9) + 4-phenoxyanilin (139-59-3) → p-phenoxyphenylisocyanate (59377-19-4)

Conditions	Yield
In dichloromethane at 0℃; Inert atmosphere;
With triethylamine In dichloromethane at 0 - 20℃; for 6h;

p-phenoxyphenylisocyanate (59377-19-4) + 7-ethoxy-6-methoxy-4-piperazin-1-yl-quinazoline → 4-(7-Ethoxy-6-methoxy-4-quinazolinyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	100%
With triethylamine

p-phenoxyphenylisocyanate (59377-19-4) + 6-ethoxy-7-methoxy-4-piperazin-1-yl-quinazoline → 4-(6-Ethoxy-7-methoxy-4-quinazolinyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	100%
With triethylamine

p-phenoxyphenylisocyanate (59377-19-4) + 7-chloro-4-piperazinylquinoline (837-52-5) → 4-(7-Chloro-4-quinolyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
	100%

p-phenoxyphenylisocyanate (59377-19-4) + 1-(1-piperazinyl)-isoquinoline (126653-00-7) → 4-(1-isoquinolyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	100%

p-phenoxyphenylisocyanate (59377-19-4) + 6-methoxy-7-(2-methoxy-ethoxy)-4-piperazin-1-yl-quinazoline (461429-70-9) → {4-[6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yl]piperazinyl}-N-(4-phenoxyphenyl)carboxamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	100%

p-phenoxyphenylisocyanate (59377-19-4) + 4-chloro-1-(1-piperazinyl)phthalazine (223587-51-7) → 4-(4-Chloro-1-phthalazinyl)-N-(4-Phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	100%

p-phenoxyphenylisocyanate (59377-19-4) + 4-(piperazin-1-yl)-7-(trifluoromethyl)quinoline → N-(4-Phenoxyphenyl)-4-(7-trifluoromethyl-4-quinolyl)-1-piperazinecarboxamide

Conditions	Yield
	100%

p-phenoxyphenylisocyanate (59377-19-4) + 7-isopropoxy-6-methoxy-4-piperazin-1-yl-quinazoline → 4-(7-Isopropoxy-6-methoxy-4-quinazolinyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	100%

p-phenoxyphenylisocyanate (59377-19-4) + methanesulfonic acid 7-methoxy-4-piperazin-1-yl-quinazolin-6-yl ester → 4-(6-Mesyloxy-7-methoxy-4-quinazolinyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	100%

p-phenoxyphenylisocyanate (59377-19-4) + 6,7-dimethoxy-4-piperazin-1-yl-quinoline-3-carboxylic acid ethyl ester → 4-(6,7-Dimethoxy-3-ethoxycarbonyl-4-quinolyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	100%

p-phenoxyphenylisocyanate (59377-19-4) + 8-chloro-4-(1-piperazinyl)quinoline → 4-(8-Chloro-4-quinolyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
	99%

3-{4-[1-(trans-4-tert-Butyl-cyclohexylamino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-benzoylamino}-propionic acid ethyl ester (777863-87-3) + p-phenoxyphenylisocyanate (59377-19-4) → 3-{4-[1-[1-(4-tert-butyl-cyclohexyl)-3-(4-phenoxy-phenyl)-ureido]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-benzoylamino}-propionic acid ethyl ester (777863-94-2)

Conditions	Yield
In tetrahydrofuran for 12h;	99%

p-phenoxyphenylisocyanate (59377-19-4) + 4-(6,7-difluoro-4-quinazolinyl)-1-piperazinecarboxylic acid tert-butyl ester (205259-36-5) → 4-(6,7-Difluoro-4-quinazolinyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
With triethylamine; trifluoroacetic acid In N-methyl-acetamide; dichloromethane	98%

p-phenoxyphenylisocyanate (59377-19-4) + 6,7-dimethoxy-4-(1-piperazinyl)quinazoline (21584-72-5) → PDGF Receptor Tyrosine Kinase Inhibitor III

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	97%

Cyanoacetohydrazide (140-87-4) + p-phenoxyphenylisocyanate (59377-19-4) → α-cyanoacetic acid 2-(4-phenoxyphenylaminocarbonyl) hydrazide (119769-15-2)

Conditions	Yield
In acetonitrile for 0.75h;	96%

(R)-2-methylamino-1-phenylpropane (33817-09-3) + p-phenoxyphenylisocyanate (59377-19-4) → 1-Methyl-1-((R)-1-methyl-2-phenyl-ethyl)-3-(4-phenoxy-phenyl)-urea

Conditions	Yield
In dichloromethane at 20℃; for 18h;	96%

p-phenoxyphenylisocyanate (59377-19-4) + 4-(1,4-diazepan-1-yl)-6,7-dimethoxyquinazoline → 4-(6,7-Dimethoxy-4-quinazolinyl)-N-(4-phenoxyphenyl)-1-homopiperazinecarboxamide

Conditions	Yield
In N,N-dimethyl-formamide	95%

p-phenoxyphenylisocyanate (59377-19-4) → 4'-Formylaminobiphenyl ether

Conditions	Yield
With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; 2-methyltetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; chemoselective reaction;	94%

p-phenoxyphenylisocyanate (59377-19-4) + 6,7-dimethoxy-2-methyl-4-(1-piperazinyl)quinazoline → 4-(6,7-Dimethoxy-2-methyl-4-quinazolinyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide

Conditions	Yield
	93%

p-phenoxyphenylisocyanate (59377-19-4) + 4-piperazinylquinoline (118306-89-1) → 4-quinolin-4-yl-piperazine-1-carboxylic acid (4-phenoxy-phenyl)-amide

Conditions	Yield
	93%

4-amino-phenol (123-30-8) + p-phenoxyphenylisocyanate (59377-19-4) → 1-(4-hydroxyphenyl)-3-(4-phenoxyphenyl)urea (1380411-49-3)

Conditions	Yield
In acetonitrile	93%
In acetonitrile at 20℃;	88%
In acetonitrile at 20℃; Inert atmosphere;

p-phenoxyphenylisocyanate (59377-19-4) + quinine (56-54-2, 130-95-0, 572-59-8, 572-60-1, 42151-59-7, 47342-58-5, 72402-50-7, 72402-51-8, 72402-52-9, 72402-53-0, 101143-86-6, 101143-87-7, 101143-88-8, 146925-10-2) → C33H33N3O4

Conditions	Yield
In toluene for 12h; Reflux;	92%

(1S,2R)-(+)-ephedrine (321-98-2) + p-phenoxyphenylisocyanate (59377-19-4) → 1-((1R,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-1-methyl-3-(4-phenoxy-phenyl)-urea

Conditions	Yield
In dichloromethane at 20℃; for 18h;	91%

(1S,2R)-(+)-norphedrine (37577-28-9) + p-phenoxyphenylisocyanate (59377-19-4) → 1-((1R,2S)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-3-(4-phenoxy-phenyl)-urea

Conditions	Yield
In dichloromethane at 20℃; for 18h;	91%

p-phenoxyphenylisocyanate (59377-19-4) + dl-4-chloromethamphetamine hydrochloride → 1-[2-(4-chloro-phenyl)-1-methyl-ethyl]-1-methyl-3-(4-phenoxy-phenyl)-urea

Conditions	Yield
In dichloromethane at 20℃; for 18h;	91%

2-amino-benzthiazole (136-95-8) + p-phenoxyphenylisocyanate (59377-19-4) → 1-(benzo[d]thiazol-2-yl)-3-(4-phenoxyphenyl)urea (218136-20-0)

Conditions	Yield
In acetonitrile at 20℃;	91%

1-(2-pyrrolidin-1-ylethyl)-1H-indazol-4-ylamine (848779-68-0) + p-phenoxyphenylisocyanate (59377-19-4) → 1-(4-phenoxy-phenyl)-3-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-4-yl]-urea

Conditions	Yield
In tetrahydrofuran at 60℃;	90%

1-(2-pyrrolidin-1-ylethyl)-1H-indazol-6-ylamine (848779-64-6) + p-phenoxyphenylisocyanate (59377-19-4) → 1-(4-phenoxy-phenyl)-3-[1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-yl]-urea

Conditions	Yield
In tetrahydrofuran at 60℃;	90%

1-(2-pyrrolidin-1-ylethyl)-1H-indazol-5-ylamine (690265-60-2) + p-phenoxyphenylisocyanate (59377-19-4) → N-(4-phenoxyphenyl)-N'-[1-(2-pyrrolidin-1-ylethyl)-1H-indazol-5-yl]urea

Conditions	Yield
In tetrahydrofuran at 60℃;	90%
In tetrahydrofuran at 50℃; for 1h;	79%
In tetrahydrofuran at 50℃; for 1h;
In tetrahydrofuran at 50℃; for 1h;

trimethyl(difluoromethyl)silane (65864-64-4) + p-phenoxyphenylisocyanate (59377-19-4) → 2,2-difluoro-N-(4-phenoxyphenyl)acetamide

Conditions	Yield
With potassium 2-methylbutan-2-olate In tetrahydrofuran at 0℃; Inert atmosphere;	90%

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 139-59-3 4-phenoxyanilin 
• 2215-77-2 4-Phenoxybenzoic acid 
• 503-38-8 trichloromethyl chloroformate 
• 75-44-5 phosgene 

Downstream Products

• 119769-15-2 α-cyanoacetic acid 2-(4-phenoxyphenylaminocarbonyl) hydrazide 
• 86764-54-7 1,1-Dibenzyl-3-(4-phenoxy-phenyl)-urea 
• 777863-94-2 3-{4-[1-[1-(4-tert-butyl-cyclohexyl)-3-(4-phenoxy-phenyl)-ureido]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-benzoylamino}-propionic acid ethyl ester 
• 854921-85-0 N-[1-(2,2-dimethoxyethyl)-1H-indazol-6-yl]-N'-(4-phenoxyphenyl)urea 
• 617244-40-3 2-methoxy-4-[3-(4-phenoxy-phenyl)-ureido]-benzoic acid 
• 1059702-77-0 (R)-3-(3-(4-phenoxyphenyl)ureido)-4-(trimethylammonio)butanoate 
• 1087160-30-2 C₂₇H₃₅N₃O₃ 
• 1265476-92-3 4-({[(4'-phenoxyphenyl)amino]carbonyl}amino)benzenesulfonamide 
• 878132-31-1 1-[1-(3,3-dimethoxy-propyl)-1H-indazol-5-yl]-3-(4-phenoxy-phenyl)-urea 

Relevant articles and documents

Electrochemically Enabled Intramolecular Aminooxygenation of Alkynes via Amidyl Radical Cyclization

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