701-82-6

Basic information

• Product Name: 3-HYDROXYPHENYLUREA
• Synonyms: (3-hydroxyphenyl)-ure;N-CARBAMYL-M-AMINOPHENOL;N-CARBAMOYL-3-AMINOPHENOL;N-CARBAMYL-3-AMINOPHENOL;M-HYDROXYPHENYL UREA;1-(3-HYDROXYPHENYL)UREA;3-HYDROXYPHENYLUREA;1-(3-HYDROXYPHENYL)UREA 98%
• CAS NO: 701-82-6
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• EINECS: 211-860-3
• Mol File: 701-82-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 182-184 °C(lit.)
• Boiling Point: 274.61°C (rough estimate)
• Flash Point: 143.2 °C
• Appearance: beige fine crystalline powder
• Density: 1.407
• Vapor Pressure: 0.000276mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• PKA: 9.69±0.10(Predicted)
• CAS DataBase Reference: 3-HYDROXYPHENYLUREA(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYPHENYLUREA(701-82-6)
• EPA Substance Registry System: 3-HYDROXYPHENYLUREA(701-82-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 701-82-6(Hazardous Substances Data)

Usage

Chemical Properties

beige fine crystalline powder

InChI:InChI=1/C7H8N2O2/c8-7(11)9-5-2-1-3-6(10)4-5/h1-4,10H,(H3,8,9,11)

Synthetic route

sodium isocyanate (917-61-3) + m-Hydroxyaniline (591-27-5) → 1-(3-hydroxyphenyl)urea (701-82-6)

Conditions	Yield
With acetic acid In water at 20℃; for 1h;	92%
With acetic acid In water at 20 - 25℃;	85%

potassium cyanate (590-28-3) + m-Hydroxyaniline (591-27-5) → 1-(3-hydroxyphenyl)urea (701-82-6)

Conditions	Yield
With hydrogenchloride In water at 20℃; for 12h; Inert atmosphere;	67%

potassium cyanate (590-28-3) + 3-amino-phenol hydrochloride → 1-(3-hydroxyphenyl)urea (701-82-6)

Conditions	Yield
With water

potassium cyanate (590-28-3) + water (7732-18-5) + 3-aminophenol hydrochloride (51-81-0) → 1-(3-hydroxyphenyl)urea (701-82-6)

3-Carboxyphenol (99-06-9) → 1-(3-hydroxyphenyl)urea (701-82-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0.08 h / 0 °C / Inert atmosphere 2: sodium azide; dmap / toluene; N,N-dimethyl-formamide / Inert atmosphere 3: ammonium hydroxide / toluene; N,N-dimethyl-formamide; water / 90 °C / Inert atmosphere View Scheme

C19H15O4P → 1-(3-hydroxyphenyl)urea (701-82-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide; dmap / toluene; N,N-dimethyl-formamide / Inert atmosphere 2: ammonium hydroxide / toluene; N,N-dimethyl-formamide; water / 90 °C / Inert atmosphere View Scheme

3-hydroxy-benzoyl azide (89975-51-9) → 1-(3-hydroxyphenyl)urea (701-82-6)

Conditions	Yield
With ammonium hydroxide In water; N,N-dimethyl-formamide; toluene at 90℃; Curtius Rearrangement; Inert atmosphere;	107 mg

1-(3-hydroxyphenyl)urea (701-82-6) → 4-amino-2-hydroxybenzamide (5985-89-7)

Conditions	Yield
With aluminium trichloride for 0.075h; Fries rearrangement; microwave irradiation;	94%

1-bromo-hexane (111-25-1) + 1-(3-hydroxyphenyl)urea (701-82-6) → N-carbamoyl-m-aminohexyloxybenzene

Conditions	Yield
With potassium carbonate In methanol for 48h; Heating;	85%

1-(3-hydroxyphenyl)urea (701-82-6) + 1-benzyl-3,5-dichloro-6-methylpyrazin-2(1H)-one (173200-35-6) → 1-(4-benzyl-6-chloro-5-methyl-3-oxo-3,4-dihydropyrazin-2-yl)-3-(3-hydroxyphenyl)urea

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,2-dimethoxyethane at 80 - 100℃; Microwave irradiation;	84%

1-(3-hydroxyphenyl)urea (701-82-6) + 2-(3,4,5-trimethoxyphenyl)-2-oxoacetaldehyde (150114-69-5) → 1-(3-hydroxyphenyl)-5-(3,4,5-trimethoxyphenyl)imidazolidine-2,4-dione

Conditions	Yield
With hydrogenchloride; acetic acid In water at 50℃; for 1h;	80%
With hydrogenchloride; acetic acid In water at 50℃; for 1h;	80%

1-Bromotetradecane (112-71-0) + 1-(3-hydroxyphenyl)urea (701-82-6) → N-carbamoyl-m-aminotetradecyloxybenzene

Conditions	Yield
With potassium carbonate In methanol for 48h; Heating;	79%

1-bromo dodecane (112-29-8) + 1-(3-hydroxyphenyl)urea (701-82-6) → N-carbamoyl-aminodecyloxybenzene

Conditions	Yield
With potassium carbonate In methanol for 48h; Heating;	70%

1-(3-hydroxyphenyl)urea (701-82-6) + licochalcone A (87080-27-1, 58749-22-7) → 6-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-4-(4-hydroxyphenyl)-1-(3-hydroxyphenyl)-5,6-dihydropyrimidin-2-one

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide; toluene at 80℃; for 6h;	52.75%

1-(3-hydroxyphenyl)urea (701-82-6) → tris(3-ureylphenyl) phosphite (222610-52-8)

Conditions	Yield
With triethylamine; phosphorus trichloride In chloroform; N,N-dimethyl-formamide at 0 - 20℃;	30%

1-(3-hydroxyphenyl)urea (701-82-6) + 2-Bromo-4'-methoxyacetophenone (2632-13-5) → C16H14N2O3

Conditions	Yield
In ethanol; N,N-dimethyl-formamide for 7h; Sealed tube; Reflux;	26%

1-(3-hydroxyphenyl)urea (701-82-6) + cinnamoyl chloride (102-92-1) → (3-cinnamoyloxy-phenyl)-urea

Conditions	Yield
With sodium hydroxide; diethyl ether

1-(3-hydroxyphenyl)urea (701-82-6) + benzoyl chloride (98-88-4) → (3-benzoyloxy-phenyl)-urea

Conditions	Yield
With pyridine

1-(3-hydroxyphenyl)urea (701-82-6) + aniline (62-53-3) → 1-(3-hydroxyphenyl)-3-phenylurea (13142-80-8)

Conditions	Yield
at 180 - 190℃;

1-(3-hydroxyphenyl)urea (701-82-6) + m-Hydroxyaniline (591-27-5) → N,N'-bis(3-hydroxyphenyl)urea (3746-46-1)

Conditions	Yield
at 180 - 190℃;

1-(3-hydroxyphenyl)urea (701-82-6) + 3-chloro-4-(methylamino)aniline (6085-54-7) → {6-[(E)-3-Chloro-4-methylamino-phenylimino]-3-oxo-cyclohexa-1,4-dienyl}-urea (56331-10-3)

Conditions	Yield
With ammonium peroxydisulfate In water; acetone

1-(3-hydroxyphenyl)urea (701-82-6) + 4-amino-N-ethyl-N-(carbamylmethyl)-aniline (2628-69-5) → C17H19N5O3 (55302-77-7)

Conditions	Yield
(i) acetone, H2O, aq. NH3, (ii) aq. (NH4)2S2O8; Multistep reaction;
With ammonium hydroxide; ammonium peroxydisulfate In acetone

1-(3-hydroxyphenyl)urea (701-82-6) + 2-(4-amino-2-chloro-anilino)-ethanol (26849-78-5) → {6-[(Z)-3-Chloro-4-(2-hydroxy-ethylamino)-phenylimino]-3-oxo-cyclohexa-1,4-dienyl}-urea (56330-90-6)

Conditions	Yield
With ammonium peroxydisulfate In water; acetone

1-(3-hydroxyphenyl)urea (701-82-6) + 3-methyl-4-amino-N-ethyl-N-(carbamoylmethyl)aniline (46409-67-0) → C18H21N5O3 (55303-74-7)

Conditions	Yield
With hydrogenchloride; ammonium peroxydisulfate

1-(3-hydroxyphenyl)urea (701-82-6) + N4-Ethyl-2-methyl-benzene-1,4-diamine; hydrochloride → {6-[(Z)-4-Ethylamino-2-methyl-phenylimino]-3-oxo-cyclohexa-1,4-dienyl}-urea (56330-24-6)

Conditions	Yield
With ammonium peroxydisulfate In water; acetone

1-(3-hydroxyphenyl)urea (701-82-6) + 2-[(4-Amino-3-methyl-phenyl)-ethyl-amino]-acetamide; hydrochloride → C18H21N5O3 (55303-74-7)

Conditions	Yield
(i) iPrOH, aq. NH3, (ii) aq. (NH4)2S2O8; Multistep reaction;

1-(3-hydroxyphenyl)urea (701-82-6) + 2-chloro-4-amino-N-methyl aniline sulfate → {6-[(E)-3-Chloro-4-methylamino-phenylimino]-3-oxo-cyclohexa-1,4-dienyl}-urea (56331-10-3)

Conditions	Yield
With ammonium peroxydisulfate In water; acetone

1-(3-hydroxyphenyl)urea (701-82-6) + 2-[(4-Amino-2-methyl-phenyl)-methyl-amino]-ethanol; compound with sulfuric acid → C17H20N4O3 (55303-75-8)

Conditions	Yield
(i) acetone, H2O, aq. NH3, (ii) aq. (NH4)2S2O8; Multistep reaction;

1-(3-hydroxyphenyl)urea (701-82-6) + 2-(4-Amino-2-chloro-phenylamino)-ethanol; compound with sulfuric acid → {6-[(Z)-3-Chloro-4-(2-hydroxy-ethylamino)-phenylimino]-3-oxo-cyclohexa-1,4-dienyl}-urea (56330-90-6)

Conditions	Yield
With ammonium peroxydisulfate In water; acetone

1-(3-hydroxyphenyl)urea (701-82-6) + N-[2-(4-Amino-2-methyl-phenylamino)-ethyl]-acetamide; compound with sulfuric acid → N-(2-{2-Methyl-4-[4-oxo-2-ureido-cyclohexa-2,5-dien-(Z)-ylideneamino]-phenylamino}-ethyl)-acetamide

Conditions	Yield
With ammonium peroxydisulfate In water; acetone

1-(3-hydroxyphenyl)urea (701-82-6) + N-[2-(4-Amino-2-chloro-phenylamino)-ethyl]-methanesulfonamide; compound with sulfuric acid → N-(2-{2-Chloro-4-[4-oxo-2-ureido-cyclohexa-2,5-dien-(Z)-ylideneamino]-phenylamino}-ethyl)-methanesulfonamide

Conditions	Yield
With ammonium peroxydisulfate In water; acetone

1-(3-hydroxyphenyl)urea (701-82-6) + N4-Ethyl-2-methyl-benzene-1,4-diamine → {6-[(Z)-4-Ethylamino-2-methyl-phenylimino]-3-oxo-cyclohexa-1,4-dienyl}-urea (56330-24-6)

Conditions	Yield
With ammonium peroxydisulfate In water; acetone at 0℃;

1-(3-hydroxyphenyl)urea (701-82-6) + 2-[(4-Amino-2-methyl-phenyl)-methyl-amino]-ethanol → C17H20N4O3 (55303-75-8)

Conditions	Yield
With ammonium hydroxide; ammonium peroxydisulfate In acetone

Upstream product

• 590-28-3 potassium cyanate 
• 591-27-5 m-Hydroxyaniline 
• 89975-51-9 3-hydroxy-benzoyl azide 
• 99-06-9 3-Carboxyphenol 
• 917-61-3 sodium isocyanate 
• 7732-18-5 water 
• 51-81-0 3-aminophenol hydrochloride 

Downstream Products

• 3746-46-1 N,N'-bis(3-hydroxyphenyl)urea 
• 591-27-5 m-Hydroxyaniline 
• 859787-23-8 C₁₀H₁₂N₂O₃ 
• 13142-80-8 1-(3-hydroxyphenyl)-3-phenylurea 
• 1079042-79-7 C₁₄H₁₀N₄O₄ 
• 57839-16-4 {2-[3-Chloro-4-(2-hydroxy-ethylamino)-phenylamino]-5-hydroxy-phenyl}-urea 
• 57838-80-9 [2-(4-Ethylamino-2-methyl-phenylamino)-5-hydroxy-phenyl]-urea 
• 57839-14-2 [2-(3-Chloro-4-methylamino-phenylamino)-5-hydroxy-phenyl]-urea 
• 5985-89-7 4-amino-2-hydroxybenzamide 

Relevant articles and documents

Direct conversion of carboxylic acids to various nitrogen-containing compounds in the one-pot exploiting curtius rearrangement

Herein we report, a single-pot multistep conversion of inactivated carboxylic acids to various N-containing compounds using a common synthetic methodology. The developed methodology rendered the use of carboxylic acids as a direct surrogate of primary amines, for the synthesis of primary ureas, secondary/tertiary ureas, O/S-carbamates, benzoyl ureas, amides, and N-formyls, exploiting the Curtius reaction. This approach has a potential to provide a diversified library of N-containing compounds, starting from a single carboxylic acid, based on the selection of the nucleophile.

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