591-27-5

Basic information

• Product Name: 3-Aminophenol
• Synonyms: 1-Amino-3-hydroxybenzene;1-amino-3-hydroxybenzene[qr];3-amino-1-hydroxybenzene[qr];3-amino-pheno;3-hydroxyaniline[qr];3-Hydroxyanilinel AC;3-hydroxybenzenamine;Basf ursol eg
• CAS NO: 591-27-5
• Molecular Formula: C₆H₇NO
• Molecular Weight: 109.13
• EINECS: 209-711-2
• Product Categories: Aromatic Phenols;Anilines, Aromatic Amines and Nitro Compounds;Organics;Phenoles and thiophenoles;API intermediates;Organic Chemicals;Organic Building Blocks;Oxygen Compounds;Phenols;AM to AQChemical Class;A;A-BAlphabetic;Alpha sort;Amines;Aromatics;Pesticides&Metabolites;Pyridines ,Halogenated Heterocycles
• Mol File: 591-27-5.mol
• Article Data: 173

Chemical Properties

• Melting Point: 121 °C
• Boiling Point: 164 °C11 mm Hg(lit.)
• Flash Point: 155 °C
• Appearance: White to pinkish or light gray/Crystalline Powder
• Density: 0.99
• Vapor Pressure: 0.019Pa at 20℃
• Refractive Index: 1.5444 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 26g/l
• PKA: 4.37, 9.82(at 20℃)
• Water Solubility: 35 g/L (20 ºC)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, bases, mineral acids. May be light or air-sensitive.
• Merck: 14,460
• BRN: 636059
• CAS DataBase Reference: 3-Aminophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminophenol(591-27-5)
• EPA Substance Registry System: 3-Aminophenol(591-27-5)

Safety Data

• Hazard Codes: Xn,N
• Statements: 20/22-51/53
• Safety Statements: 28-61-28A
• RIDADR: UN 2512 6.1/PG 3
• WGK Germany: 2
• RTECS: SJ4900000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 591-27-5(Hazardous Substances Data)

Usage

Chemical Properties

Light grey crystal powder

Uses

Different sources of media describe the Uses of 591-27-5 differently. You can refer to the following data:
1. m-Aminophenol (MAP) is an important starting material for dyes, including a variety of leuco (or latent) dyes used in imaging technology, optical bleaches and fluorescent agents, drugs, agricultural chemicals; and high-performance polymers. Although the synthesis of m-aminophenol(s) by the reaction of resorcinol with ammonia or (di)alkylarnines has been known for about 100 years,the preferred manufacturing process had been for many years a route involving the sulfonation of nitrobenzene to m-nitrobenzenesulfonic acid, the reduction of the nitro group to give m-aminobenzenesulfonic acid, followed by the caustic fusion of sodium m-aminobenzenesulfonate to yield sodium m-aminophenolate. The m-aminophenol was isolated/purified by neutralization, filtration, and recrystallization; the overall yield of m-aminophenol from nitrobenzene was estimated by SRI International to be 58%. (Doubtless, process improvements were made by the producers using this process.) The nitrobenzene/sulfonationlreductionlcaustic fusion route is still being used commercially, notably by ACNA in Italy, the largest producer of MAP, as well as a few smaller manufacturers. Sumitomo Chemical Co. used this process as well into the early 1980s and had licensed their knowhow to Hindustani Organic Chemicals, Ltd. of India which started up a plant on this basis with a capacity for MAP of 1.5 mill. lb /yr in 1970.The output of the Indian plant was said to be devoted to making sodium p-aminosalycilate (PAS), a tuberculostatic agent.
2. 3-Aminophenol is an aromatic compound used in the preparation of inhibitors of mammalian carbonic anhydrase isoforms. Also used in the preparation of quinoline tethered fluorescent carbon dots for regulated anticancer discovery.
3. Dye intermediate, manufacture of p-aminosalicylic acid.

Definition

ChEBI: An aminophenol that is one of three amino derivatives of phenol which has the single amino substituent located meta to the phenolic -OH group.

Application

3-Aminophenol has been used in the synthesis of disulfonated bis[4-(3-aminophenoxy)phenyl]sulfone (S-BAPS).It can be used to synthesize:Methyl 2-oxo-7-[(triphenylphosphoranylidene)amino]-2H-chromene-4-carboxylate by reacting with dimethyl acetylenedicarboxylate (DMAD) in the presence of triphenylphosphine.3-Amino-2-cyclohexen-1-one via palladium-catalyzed hydrogenation.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 1479, 1984 DOI: 10.1016/S0040-4039(01)80191-X

General Description

White crystals or off-white flakes.

Air & Water Reactions

3-Aminophenol may be sensitive to prolonged exposure to air and light. Slightly soluble in water.

Reactivity Profile

3-Aminophenol may react with strong oxidizers and mineral acids or bases.

Hazard

Toxic by ingestion.

Fire Hazard

Flash point data for 3-Aminophenol are not available. 3-Aminophenol is probably combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by ingestion, subcutaneous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. A skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx,.

Purification Methods

Crystallise it from hot water or toluene. [Beilstein 13 IV 952.]

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

InChI:InChI=1/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2

Synthetic route

meta-nitrophenol (554-84-7) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With hydrogen In ethanol at 60℃; under 7500.75 Torr; for 2h;	100%
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 12h;	100%
With sodium tetrahydroborate In methanol; water at 20℃; for 3h;	100%

m-tetrahydropyran-2-yloxyaminobenzene (147985-36-2) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With β‐cyclodextrin In water at 60℃; for 0.133333h; Microwave irradiation;	99%
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry;	95%

3-(benzyloxy)nitrobenzol (24318-00-1) → 3-(benzyloxy)aniline (1484-26-0) + m-Hydroxyaniline (591-27-5)

Conditions	Yield
With pyrrolidine; hydrogen; 5% rhodium-on-charcoal; iron(II) acetate In tetrahydrofuran at 20℃; for 2.5h;	A 98% B 0.5%
With hydrogen; 5% rhodium-on-charcoal; nickel(II) nitrate In tetrahydrofuran; water at 20℃; for 15h;	A 92% B 2%
With hydrogen; 5% rhodium-on-charcoal; iron(II) acetate In tetrahydrofuran at 20℃; for 33h;	A 92% B 0.8%

3-(methoxymethoxy)aniline (96649-05-7) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With β‐cyclodextrin In water at 60℃; for 0.15h; Microwave irradiation;	98%
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry;	93%

3-azidophenol (51642-25-2) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With ammonium hydroxide at 90℃; for 1h;	97%
With aluminium(III) iodide In benzene for 0.25h; Reduction; Heating;	92%
With triphenylphosphine-2-carboxamide In tetrahydrofuran; water at 20℃; for 2h; Staudinger Azide Reduction;	90%

3-amino-4-bromophenol (100367-37-1) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With sodium sulfite In water at 60℃; for 18h; Green chemistry;	96%

tert-butyl 3-hydroxyphenylcarbamate (19962-06-2) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With water at 100℃; for 1h;	95%

3-Iodophenol (626-02-8) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 120℃; for 16h; Sealed tube;	95%

m-phenylenediamine (108-45-2) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With sulfuric acid; sodium nitrite at 10 - 90℃;	92.8%
Diazotization.ueber mehrere Stufen;

3-[(tert-butyldimethylsilyl)oxy]aniline (121942-75-4) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With sodium phosphate dodecahydrate In N,N-dimethyl-formamide at 20℃; for 2h;	92%
With potassium hydroxide In ethanol at 20℃; for 2h;	91%

3-(benzyloxy)nitrobenzol (24318-00-1) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol at 60℃; under 3000.3 Torr; for 3h;	92%

2-bromo-3-hydroxyaniline (100367-36-0) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With sodium sulfite In water at 60℃; for 18h; Green chemistry;	91%

3-Aminophenylboronic acid (30418-59-8) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With 1,10-Phenanthroline; copper(II) sulfate; potassium hydroxide In water at 20℃; for 3h;	90%
With water; caesium carbonate; hydrazine hydrate at 80℃; for 12h;	85%
With oxygen; N-ethyl-N,N-diisopropylamine In acetone at 25℃; under 760.051 Torr; for 65h; Catalytic behavior; Irradiation;	32 %Chromat.

3-[(tert-butyldimethylsilyl)oxy]aniline (121942-75-4) + Cs2CO3 → m-Hydroxyaniline (591-27-5)

Conditions	Yield
In water; N,N-dimethyl-formamide at 20℃; for 3h;	88%

3-pyridyl diethylcarbamate (51581-40-9) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With zirconocene dichloride In tetrahydrofuran at 20℃; Inert atmosphere;	87%

3-(benzyloxy)aniline (1484-26-0) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With 10% Pd/C; cyclohexa-1,4-diene In ethyl acetate at 100℃; for 0.5h; Microwave irradiation;	86%
In ethanol for 2h; Cooling with ice;	48%
Multi-step reaction with 2 steps 1: 94 percent 2: 71.4 percent / TFSA / trifluoroacetic acid / 0 °C View Scheme

3-azidophenyl benzyl ether (107826-08-4) → 3-(benzyloxy)aniline (1484-26-0) + m-Hydroxyaniline (591-27-5)

Conditions	Yield
With trifluorormethanesulfonic acid In trifluoroacetic acid at 0℃;	A 28.5% B 71.4%

3-amino-cyclohex-2-enone (5220-49-5) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With mercury(II) diacetate In acetonitrile for 20h; Heating;	56%

recorcinol (108-46-3) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide In 1,4-dioxane at 170℃; for 16h; Molecular sieve; Inert atmosphere;	44%
With ammonium hydroxide; ammonium chloride at 200℃;
With ammonium chloride; ammonia at 200℃;

3-Aminophenylboronic acid (30418-59-8) → 3-biphenyl amine (2243-47-2) + 3,3'-diaminobiphenyl (2050-89-7) + m-Hydroxyaniline (591-27-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene for 20h; Dimerization; Heating;	A 5% B 44% C 14%

3-hydroxy-alpha-methylstyrene (51985-06-9) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
Stage #1: 3-hydroxy-alpha-methylstyrene With sodium azide; sulfuric acid In hexane; water at 20 - 40℃; for 4h; Stage #2: With sodium hydroxide In water at 0℃; for 0.333333h; Reagent/catalyst;	40%

aniline (62-53-3) → 4-amino-phenol (123-30-8) + 2-amino-phenol (95-55-6) + m-Hydroxyaniline (591-27-5)

Conditions	Yield
With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride at -20℃; for 0.25h;	A 14% B 20.5% C 36%
With dihydrogen peroxide; antimony pentafluoride In hydrogen fluoride at -20℃; for 0.25h;	A 14% B 20.5% C 36%
With dihydrogen peroxide; antimony pentafluoride In hydrogen fluoride at -20℃; for 0.25h; Mechanism; Product distribution;	A 14% B 20.5% C 36%
With bismuth(III) oxobromide; 18O-labeled water; oxygen-18 Reagent/catalyst; Photolysis;

2-hydroxy-4-nitrobenzoic acid (619-19-2) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
mit den ueblichen Reduktionsmitteln;
bei Einw. der ueblichen Reduktionsmittel;

4-(3-hydroxy-anilino)-pent-3-en-2-one + furan-2,3,5(4H)-trione pyridine (1:1) → acetic acid (64-19-7) + acetone (67-64-1) + m-Hydroxyaniline (591-27-5)

Conditions	Yield
bei der Destillation;

3-aminobenzenesulfonic acid (121-47-1) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With sodium hydroxide; water at 280 - 290℃;
With sodium hydroxide at 280 - 290℃;
With sodium hydroxide; water at 280 - 290℃;

recorcinol (108-46-3) → m-phenylenediamine (108-45-2) + m-Hydroxyaniline (591-27-5)

Conditions	Yield
With aluminum oxide; ammonia at 420℃;

phenylsulfonyl azide (938-10-3) + phenol (108-95-2) → 4-amino-phenol (123-30-8) + 2-amino-phenol (95-55-6) + m-Hydroxyaniline (591-27-5)

Conditions	Yield
at 120℃; Product distribution; anschl. Erwaermen mit wss. HCl;

meta-nitrophenol (554-84-7) → m-hydroxyphenyl-hydroxylamine (10603-61-9) + m-Hydroxyaniline (591-27-5)

Conditions	Yield
In water at 25℃; Product distribution; Mechanism; electrochemical reduction in buffered aqueous solution; pH dependence;
In ethanol; water at 25℃; Rate constant; Mechanism; Product distribution; polarographic reduction; potential-dependent rate constants kf,h, αna; pH = 1.81-11.00;

m-hydroxyphenyl-hydroxylamine (10603-61-9) → m-Hydroxyaniline (591-27-5)

Conditions	Yield
With Britton-Robbinson buffer; N-dodecylpyridinium chloride In ethanol at 25℃; Kinetics; Mechanism; electric current;
With Britton-Robbinson buffer; sodium dodecyl-sulfate In ethanol at 25℃; Kinetics; Mechanism; electric current;
With Britton-Robbinson buffer; Triton X-100 In ethanol at 25℃; Kinetics; Mechanism; electric current;

acetic anhydride (108-24-7) + m-Hydroxyaniline (591-27-5) → meta-hydroxyacetanilide (621-42-1)

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h;	100%
In tetrahydrofuran at 20℃; for 2h;	100%
With triethylamine In diethyl ether at 20℃; for 18h;	99%

ethyl acetoacetate (141-97-9) + m-Hydroxyaniline (591-27-5) → 7-amino-4-methylcoumarin. (26093-31-2)

Conditions	Yield
With zirconium(IV) phosphate at 110℃; for 0.166667h; Pechmann condensation; Microwave irradiation; chemoselective reaction;	100%
With silica gel supported zirconyl chloride octahydrate at 90℃; for 0.583333h; Pechmann condensation reaction;	98%
With tetrakis(actonitrile)copper(I) hexafluorophosphate at 25℃; for 0.166667h; Pechmann condensation; neat (no solvent);	98%

1,3-propanesultone (1120-71-4) + m-Hydroxyaniline (591-27-5) → 3-((3-hydroxyphenyl)amino)propane-1-sulfonic acid (52962-41-1)

Conditions	Yield
In acetonitrile at 20℃;	100%
In butan-1-ol for 0.5h; Heating;	80%
for 0.5h; Reflux;	80%

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + m-Hydroxyaniline (591-27-5) → 3-((trimethylsilyl)oxy)aniline (36309-43-0)

Conditions	Yield
phosphotungstic acid at 55 - 60℃; for 0.75h;	100%
With phosphotungstic acid at 55 - 60℃; for 0.75h;	99%
With silica triflate at 20℃; for 0.0333333h;	90%

3,4-dimethoxy-benzaldehyde (120-14-9) + m-Hydroxyaniline (591-27-5) → 3,4-Methoxybenzyliden-m-hydroxyanilin (23837-30-1)

Conditions	Yield
In toluene Heating;	100%

tert-butyldimethylsilyl chloride (18162-48-6) + m-Hydroxyaniline (591-27-5) → 3-[(tert-butyldimethylsilyl)oxy]aniline (121942-75-4)

Conditions	Yield
With 1H-imidazole In tetrahydrofuran at 20℃; Inert atmosphere;	100%
With 1H-imidazole In dichloromethane at 20℃; for 15h;	99%
With dmap; triethylamine In dichloromethane at 20℃; for 6h;	99.93%

benzyl chloroformate (501-53-1) + m-Hydroxyaniline (591-27-5) → 3-Hydroxycarbanilic Acid Benzyl Ester (19972-88-4)

Conditions	Yield
In diethyl ether for 18h; Ambient temperature;	100%
With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 13h;	68%
With triethylamine In diethyl ether at 20℃; for 18h;	51%
With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 1h;

2-[2-(vinyloxy)ethoxymethyl]oxirane (16801-19-7) + m-Hydroxyaniline (591-27-5) → 3-[2-Hydroxy-3-(2-vinyloxy-ethoxy)-propylamino]-phenol

Conditions	Yield
at 40 - 50℃; for 1h;	100%

di-tert-butyl dicarbonate (24424-99-5) + m-Hydroxyaniline (591-27-5) → tert-butyl 3-hydroxyphenylcarbamate (19962-06-2)

Conditions	Yield
In tetrahydrofuran Reflux;	100%
With triethylamine	99%
In tetrahydrofuran for 24h; Heating;	96%

1-acetyl-1H-1,2,3-triazolo<4,5-b>pyridine (107866-54-6) + m-Hydroxyaniline (591-27-5) → meta-hydroxyacetanilide (621-42-1)

Conditions	Yield
In tetrahydrofuran for 1h; Ambient temperature;	100%

m-Hydroxyaniline (591-27-5) → C6H6(2)HNO

Conditions	Yield
With d(4)-methanol; triethylamine for 336h; Ambient temperature;	100%

2-chloro-1,3-thiazole-5-carbonitrile (51640-36-9) + m-Hydroxyaniline (591-27-5) → 2-(3-aminophenoxy)-1,3-thiazole-5-carbonitrile (946885-69-4)

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

m-Hydroxyaniline (591-27-5) + 6,7-dimethoxy-4-chloroquinazoline (13790-39-1) → 3-(6,7-dimethoxyquinazolin-4-yloxy)-benzenamine (1188908-37-3)

Conditions	Yield
Stage #1: m-Hydroxyaniline With caesium carbonate In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 6,7-dimethoxy-4-chloroquinazoline In tetrahydrofuran at 50℃; for 24h;	100%
With tetrabutylammomium bromide; sodium hydroxide In butanone for 0.5h; Reflux;	93%
With tetrabutylammomium bromide; sodium hydroxide In water; butanone Reflux;	93%
Stage #1: m-Hydroxyaniline With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 6,7-dimethoxy-4-chloroquinazoline With potassium carbonate In N,N-dimethyl-formamide at 80 - 85℃; for 2h;	77.9%

4-chloro-6-(methylthio)-1-(prop-2-ynyl)-1H-pyrazolo[3,4-d]pyrimidine (1583284-78-9) + m-Hydroxyaniline (591-27-5) → 3-(6-(methylthio)-1-(prop-2-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenol (1583284-89-2)

Conditions	Yield
In ethanol for 12h; Reflux; Inert atmosphere;	100%

1-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine (1583284-79-0) + m-Hydroxyaniline (591-27-5) → 3-(1-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenol (1583285-03-3)

Conditions	Yield
In ethanol for 12h; Reflux; Inert atmosphere;	100%

3-(3,5-bis(trifluoromethyl)phenylimino)isobenzofuran-1(3H)-one (1253889-39-2) + m-Hydroxyaniline (591-27-5) → N1-(3,5-bis(trifluoromethyl)phenyl)-N2-(3-hydroxyphenyl)phthalamide (1615737-65-9)

Conditions	Yield
In tetrahydrofuran at 20℃; Inert atmosphere;	100%

2-bromo-1-fluoro-4-(methylsulfonyl)benzene + m-Hydroxyaniline (591-27-5) → 3-(2-bromo-4-(methylsulfonyl)phenoxy)aniline

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 120℃; for 1h; Sealed tube;	100%

5-(5-(methylsulfonyl)-2-fluorophenyl)-7-methylimidazo[1,5-a]pyrazine-8(7H)-one + m-Hydroxyaniline (591-27-5) → 5-(2-(3-aminophenoxy)-5-(methylsulfonyl)phenyl)-7-methylimidazo[1,5-a]pyrazin-8(7H)-one

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;	99.16%

chloroformic acid ethyl ester (541-41-3) + m-Hydroxyaniline (591-27-5) → ethyl N-(3-hydroxyphenyl)carbamate (7159-96-8)

Conditions	Yield
In ethyl acetate Heating;	99%
In ethyl acetate for 1h; Reflux;	93%
In ethyl acetate for 0.5h; Reflux;	93%

acrylic acid methyl ester (292638-85-8) + m-Hydroxyaniline (591-27-5) → 3-[(3-hydroxyphenyl)(2-methoxycarbonylethyl)amino]propionic acid methyl ester (59486-18-9)

Conditions	Yield
With acetic acid at 80℃; for 120h;	99%
With sodium bromide In acetic acid at 95℃; for 19h; Inert atmosphere;	86%
With acetic acid; sodium bromide at 95℃; for 19h; Inert atmosphere;	78.4%
With acetic acid; copper(l) chloride for 20h; Reflux;	65%

m-Hydroxyaniline (591-27-5) → 3-fluorophenol (372-20-3)

Conditions	Yield
With pyridine hydrogenfluoride; sodium nitrite 1.) O deg C, 20 min, 2.) 60 deg C, 1 h;	99%
Stage #1: m-Hydroxyaniline With hydrogen fluoride; sodium nitrite at -10 - -5℃; for 1h; Inert atmosphere; Stage #2: at 48 - 54℃; Concentration; Time; Temperature;	45.6%
With hydrogen fluoride; sodium nitrite at 0℃;

diethyl phosphorochloridothioate (2524-04-1) + m-Hydroxyaniline (591-27-5) → O-phenyl> O,O-diethyl phosphorothioate

Conditions	Yield
With triethylamine In chloroform at 60℃; for 3h;	99%

N-acetyl-β-phenylacetoacetamide (122664-30-6) + m-Hydroxyaniline (591-27-5) → 2,6-dimethyl-5-phenyl-1-(3'-hydroxyphenyl)-4-oxo-1,4-dihydropyrimidine (122664-42-0)

Conditions	Yield
In acetic acid for 1h;	99%
In acetic acid for 1h; Heating;	99%
With acetic acid for 1h; Heating;	60%

diethyl 2-ethoxymethylenemalonate (87-13-8) + m-Hydroxyaniline (591-27-5) → 1,3-diethyl 2-(((3-hydroxyphenyl)amino)methylidene)propanedioate (84165-81-1)

Conditions	Yield
In ethanol at 20℃; for 0.25h;	99%
With zinc(II) chloride In ethanol Heating;	89%

2,4-Dichlorophenoxyacetic acid (94-75-7) + m-Hydroxyaniline (591-27-5) → 2-(2,4-dichloro-phenoxy)-N-(3-hydroxy-phenyl)-acetamide

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	99%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	99%

4,7-dichloroquinoline (86-98-6) + m-Hydroxyaniline (591-27-5) → 4-(3'-hydroxyphenyl)amino-7-chloroquinoline (154179-33-6)

Conditions	Yield
In ethanol Reflux;	99%
for 0.25h; microwave irradiation;	75%
With hydrogenchloride; potassium iodide In ethanol Heating;

carbonic acid dimethyl ester (616-38-6) + m-Hydroxyaniline (591-27-5) → m-Anisidine (536-90-3)

Conditions	Yield
With dimanganese decacarbonyl at 180℃; for 1h;	99%

butane-2,3-dione mono-oxime (135636-66-7) + m-Hydroxyaniline (591-27-5) → N-(3-hydroxyphenyl)diacetylmonoxime

Conditions	Yield
In ethanol Reflux;	99%
In ethanol Reflux;	99%

Upstream product

• 108-45-2 m-phenylenediamine 
• 121-47-1 3-aminobenzenesulfonic acid 
• 108-46-3 recorcinol 
• 938-10-3 phenylsulfonyl azide 
• 108-95-2 phenol 
• 10603-61-9 m-hydroxyphenyl-hydroxylamine 
• 5220-49-5 3-amino-cyclohex-2-enone 
• 65-49-6 4-Aminosalicylic acid 
• 62-53-3 aniline 
• 30418-59-8 3-Aminophenylboronic acid 
• 7647-01-0 hydrogenchloride 
• 97821-22-2 t-butyl N-(m-hydroxyphenyl) sulfinamoyl acetate 
• 554-84-7 meta-nitrophenol 
• 15719-64-9 methylammonium carbonate 

Downstream Products

• 6317-89-1 3-acetamidophenyl acetate 
• 621-42-1 meta-hydroxyacetanilide 
• 26093-31-2 7-amino-4-methylcoumarin. 
• 29952-48-5 6-hydroxy-2,3-diphenyl-indole 
• 6578-02-5 2,3-diphenyl-indol-4-ol 
• 37183-25-8 2-hydroxy-N-(3-hydroxyphenyl)benzamide 
• 1226-34-2 7-hydroxy-2-phenylquinoline-4-carboxylic acid 
• 18277-39-9 N-(3-hydroxyphenyl)benzaldimine 
• 782-75-2 2-{[(3-hydroxyphenyl)imino]methyl}phenol 
• 7504-88-3 3-benzamidophenyl benzoate 
• 72239-89-5 3--1,3-diphenylprop-2-en-1-one 
• 146266-88-8 1,4-bis-(3-hydroxy-phenyl)-piperazine 

Relevant articles and documents

Preparation of resorcinarene-functionalized gold nanoparticles and their catalytic activities for reduction of aromatic nitro compounds

Resorcinarene-functionalized gold nanoparticles (AuNPs) were prepared conveniently in aqueous solution in the presence of amphiphilic tetramethoxyresorcinarene tetraaminoamide. The obtained AuNPs were characterized and analyzed by UV-vis, FT-IR, XRD and TEM, respectively. The results showed that the size of AuNPs and the standard deviations were all decreasing with the increase of resorcinarene concentration. In addition, the catalytic activity of the obtained AuNPs in the reduction of aromatic nitro compounds was also investigated. In aqueous solution the reaction follows a first order kinetics and the size of AuNPs has influence on the rate of reduction.

Pd nanoparticles supported on cubic shaped ZIF-based materials and their catalytic activates in organic reactions

Pd nanoparticles decorated on cubic shaped ZIF-based materials have been successfully prepared. The nanocomposites have been characterized by X-ray diffraction, field emission scanning electron microscopy, N2 sorption analysis, and transmission

Ag-NPs embedded in two novel Zn3/Zn5-cluster-based metal-organic frameworks for catalytic reduction of 2/3/4-nitrophenol

By utilizing symmetrical pentacarboxylate ligands, 3,5-di(2′,5′-dicarboxylphenyl)benzoic acid (H5L1) and 3,5-di(2′,4′-dicarboxylphenyl)benzoic acid (H5L2), two novel porous Zn-MOFs, [Zn5(μ3-H2O)2(L1)2]·3DMA·4H2O (CTGU-3) and [Zn3(μ3-OH)L2(H2O)3]·H2O (CTGU-4) have been synthesized under solvothermal conditions. CTGU-3 and CTGU-4 exhibit 3D microporous frameworks with flu and dia topologies and possess unique secondary building units [Zn5(μ3-H2O)2(RCO2)6] and [Zn3(μ3-OH)(RCO2)3], respectively. Such porous systems create a unique space or surface to accommodate Ag nanoparticles (Ag NPs), which could efficiently prevent Ag NPs from aggregation and leaching. In this work, two new Ag@Zn-MOF composites, denoted as Ag@CTGU, have been successfully fabricated through solution infiltration, for the reduction of nitrophenol. Compared with CTGU-4, CTGU-3 shows enhanced catalytic efficiency toward the reaction when it is used as a catalyst support of Ag NPs. Moreover, gas sorption and luminescence properties of two compounds were also investigated.

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Surface Roughness Effects of Pd-loaded Magnetic Microspheres on Reduction Kinetics of Nitroaromatics

Metal nanoparticles decoration on magnetically active semiconductor materials is a common strategy to improve the colloidal stability, catalyst harvesting, and reuse. In this study, a surfactant-free solvothermal method followed by a heat treatment to pre