16292-90-3

Basic information

• Product Name: 3-Amino-4-nitrophenol
• Synonyms: 3-Amino-4-nitrophenol;Phenol, 3-amino-4-nitro-;2-Nitro-5-hydroxyaniline;5-Hydroxy-2-nitroaniline
• CAS NO: 16292-90-3
• Molecular Formula: C₆H₆N₂O₃
• Molecular Weight: 154.12
• Mol File: 16292-90-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 183-184 °C
• Boiling Point: 396.1 °C at 760 mmHg
• Flash Point: 193.4 °C
• Appearance: /
• Density: 1.511 g/cm³
• Vapor Pressure: 7.67E-07mmHg at 25°C
• Refractive Index: 1.688
• PKA: 7.70±0.10(Predicted)
• CAS DataBase Reference: 3-Amino-4-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-4-nitrophenol(16292-90-3)
• EPA Substance Registry System: 3-Amino-4-nitrophenol(16292-90-3)

Safety Data

• Hazardous Substances Data: 16292-90-3(Hazardous Substances Data)

Usage

General Description

3-Amino-4-nitrophenol, also known as 4-Nitro-3-aminophenol, is an organic compound with the chemical formula C6H6N2O3. It is an aromatic amine and nitrophenol derivative with a yellow crystalline appearance. This chemical is commonly used in the production of dyes, pharmaceuticals, and hair dyes. It is classified as a hazardous material and should be handled with caution due to its potential health risks, including skin and eye irritation. Additionally, it is important to be aware of the environmental impact of 3-Amino-4-nitrophenol, as it can be harmful to aquatic organisms and ecosystems if not properly disposed of.

InChI:InChI=1/C6H6N2O3/c7-5-3-4(9)1-2-6(5)8(10)11/h1-3,9H,7H2

Synthetic route

N-(5-hydroxy-2-nitrophenyl)acetamide (67915-26-8) → 2-amino-4-hydroxy-1-nitrobenzene (16292-90-3)

Conditions	Yield
With hydrogenchloride; water at 110℃; for 0.0833333h; Heating;	95%
With sulfuric acid

5-chloro-2-nitroaniline (1635-61-6) → 5-chloro-2-nitrophenol (611-07-4) + 4-nitroresorcinol (3163-07-3) + 2-amino-4-hydroxy-1-nitrobenzene (16292-90-3)

Conditions	Yield
With water; sodium hydroxide at 100℃; for 50h;	A 68% B 7% C 25%
With tetra(n-butyl)ammonium hydroxide; water at 100℃; for 16h;	A 32% B 1% C 57%

3-acetamidophenyl acetate (6317-89-1) → 2-amino-4-hydroxy-1-nitrobenzene (16292-90-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid 2: sulfuric acid View Scheme

meta-hydroxyacetanilide (621-42-1) → 2-amino-4-hydroxy-1-nitrobenzene (16292-90-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid; acetic anhydride / acetic acid / 8 h / 25 °C 2: hydrogenchloride; water / 0.08 h / 110 °C / Heating View Scheme

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) → (S)-2-nitro-4-(oxiran-2-ylmethoxy)aniline (179929-91-0)

Conditions	Yield
With potassium carbonate In acetone for 18h; Reflux;	86.7%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 4-nitro-3-(1H-pyrrol-1-yl)phenol

Conditions	Yield
Stage #1: cis,trans-2,5-dimethoxytetrahydrofuran; 2-amino-4-hydroxy-1-nitrobenzene In 1,4-dioxane for 0.25h; Clauson-Kaas Synthesis; Heating; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 110℃;	70%

morpholine (110-91-8) + 2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) + 1,3-dibromo-propane (109-64-8) → 5-[3-(4-morpholinyl)propoxy]-2-nitroaniline (694533-05-6)

Conditions	Yield
Stage #1: morpholine; 1,3-dibromo-propane With pyridine Stage #2: 2-amino-4-hydroxy-1-nitrobenzene With caesium carbonate	69%

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) + (5-methoxypyrazin-2-yl)methyl methanesulfonate → 5-[(5-methoxypyrazin-2-yl)methoxy]-2-nitroaniline

Conditions	Yield
Stage #1: 2-amino-4-hydroxy-1-nitrobenzene With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: (5-methoxypyrazin-2-yl)methyl methanesulfonate In N,N-dimethyl-formamide at 20℃; for 16h;	54%

2-(morpholin-4-yl)ethanol (622-40-2) + 2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 5-(2-morpholin-4-ylethoxy)-2-nitrophenylamine (1104467-53-9)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction;	32%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 18h;

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 4-nitro-phenol (100-02-7)

Conditions	Yield
Diazotization.Verkochen des Produktes mit absol. Alkohol;
und Verkochen mit absol.Alkohol.Diazotization;

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → (5-hydroxy-2-nitro-phenyl)-arsonic acid (860557-57-9)

Conditions	Yield
With water Diazotization.anschliessend mit alkal. wss. Natriumarsenit-Loesung unter Zusatz von Kupfer(II)-sulfat;

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 3-Azido-4-nitrophenol

Conditions	Yield
(i) aq. HCl, NaNO2, (ii) NaN3; Multistep reaction;

2-(morpholin-4-yl)ethanol (622-40-2) + 2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 4-(2-morpholin-4-yl-ethoxy)-2-nitro-phenylamine

Conditions	Yield
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → (2-acetylamino-5-hydroxy-phenyl)-arsonic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: water / Diazotization.anschliessend mit alkal. wss. Natriumarsenit-Loesung unter Zusatz von Kupfer(II)-sulfat 2: ueber 6-Amino-3-hydroxy-phenylarsonsaeure View Scheme

4-chloro-2-(3-pyridyl)-6-(trifluoromethyl)pyrimidine (204394-69-4) + 2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 4-(5-Hydroxy-2-nitroanilino)-2-(3-pyridinyl)-6-trifluoromethylpyrimidine (438249-21-9)

Conditions	Yield
In hexane; ethyl acetate	55 mg (63%)

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → ethyl 3-(1-(1-(4-bromophenyl)propyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / acetonitrile / 4 h / 20 - 80 °C / Inert atmosphere 2.1: hydrogenchloride; tin(II) chloride dihdyrate / 1,4-dioxane / 160 °C / Inert atmosphere 2.2: 4 h / 90 °C 3.1: caesium carbonate / N,N-dimethyl-formamide / 72 h / 100 °C / Inert atmosphere View Scheme

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 3-{1-[1-(4-bromophenyl)propyl]-6-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl}-2,2-dimethylpropanoic acid

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydroxide / acetonitrile / 4 h / 20 - 80 °C / Inert atmosphere 2.1: hydrogenchloride; tin(II) chloride dihdyrate / 1,4-dioxane / 160 °C / Inert atmosphere 2.2: 4 h / 90 °C 3.1: caesium carbonate / N,N-dimethyl-formamide / 72 h / 100 °C / Inert atmosphere 4.1: lithium hydroxide; methanol / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 2,2-dimethyl-3-[1-(naphthalen-2-ylmethyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]propanoic acid

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide / acetonitrile / 4 h / 20 - 80 °C / Inert atmosphere 2.1: hydrogenchloride; tin(II) chloride dihdyrate / 1,4-dioxane / 160 °C / Inert atmosphere 2.2: 4 h / 90 °C 3.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 70 °C / Inert atmosphere 3.2: 40 °C View Scheme

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → ethyl 2,2-dimethyl-3-(5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)propanoate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / acetonitrile / 4 h / 20 - 80 °C / Inert atmosphere 2.1: hydrogenchloride; tin(II) chloride dihdyrate / 1,4-dioxane / 160 °C / Inert atmosphere 2.2: 4 h / 90 °C View Scheme

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) + 2-(chloromethyl)quinoline monohydrochloride (3747-74-8) → 2-nitro-5-(quinolin-2-ylmethoxy)aniline

Conditions	Yield
With sodium hydroxide In acetonitrile at 20 - 80℃; for 4h; Inert atmosphere;

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) + metronidazole (443-48-1) → 5-O-(metronidazol-2'-yl)-2-nitroaniline

Conditions	Yield
With sulfuric acid In tetrahydrofuran Reflux;	18.8 g

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 4-amino-3-(1H-pyrrol-1-yl)phenol

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,4-dioxane / 0.25 h / Heating 1.2: 110 °C 2.1: tin(II) chloride dihdyrate / ethyl acetate / 2 h / 25 °C View Scheme

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 8-hydroxypyrrolo[1,2-a]quinoxalin-4(5H)-one

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,4-dioxane / 0.25 h / Heating 1.2: 110 °C 2.1: tin(II) chloride dihdyrate / ethyl acetate / 2 h / 25 °C 3.1: toluene / 2 h / Reflux View Scheme

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → 4-oxo-4,5-dihydropyrrolo[1,2-a]quinoxalin-8-yl 6-phenylhexylcarbamate

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 1,4-dioxane / 0.25 h / Heating 1.2: 110 °C 2.1: tin(II) chloride dihdyrate / ethyl acetate / 2 h / 25 °C 3.1: toluene / 2 h / Reflux 4.1: triethylamine / tetrahydrofuran View Scheme

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → (S)-1-(4-amino-3-nitrophenoxy)-3-(4-(4-chlorophenyl)piperazin-1-yl)propan-2-ol

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 18 h / Reflux 2: ethanol / Reflux View Scheme

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → C19H25ClN4O2

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 18 h / Reflux 2: ethanol / Reflux 3: sodium hydrogencarbonate; sodium dithionite / ethanol; water / 20 °C View Scheme

2-amino-4-hydroxy-1-nitrobenzene (16292-90-3) → C20H23ClN4O3

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 18 h / Reflux 2: ethanol / Reflux 3: sodium hydrogencarbonate; sodium dithionite / ethanol; water / 20 °C 4: hydrogenchloride / water; toluene View Scheme

Upstream product

• 621-42-1 meta-hydroxyacetanilide 
• 1635-61-6 5-chloro-2-nitroaniline 
• 6317-89-1 3-acetamidophenyl acetate 
• 67915-26-8 N-(5-hydroxy-2-nitrophenyl)acetamide 

Downstream Products

• 1104467-53-9 5-(2-morpholin-4-ylethoxy)-2-nitrophenylamine 
• 694533-05-6 5-[3-(4-morpholinyl)propoxy]-2-nitroaniline 
• 179929-91-0 (S)-2-nitro-4-(oxiran-2-ylmethoxy)aniline 
• 860557-57-9 (5-hydroxy-2-nitro-phenyl)-arsonic acid 
• 100-02-7 4-nitro-phenol 

Relevant articles and documents

Development of Potent Inhibitors of Fatty Acid Amide Hydrolase Useful for the Treatment of Neuropathic Pain

The unique role of fatty acid amide hydrolase (FAAH) in terminating endocannabinoid (EC) signaling supports its relevance as a therapeutic target. Inhibition of EC metabolizing enzymes elicits indirect agonism of cannabinoid receptors (CBRs) and therapeutic efficacy devoid of psychotropic effects. Based on our previous ligands, and aiming at the discovery of new selective FAAH inhibitors, we developed a series of 12 new compounds characterized by functionalized tricyclic scaffolds. All the developed compounds display negligible activity on monoacylglycerol lipase (MAGL) and CBRs. The most potent FAAH inhibitors of the newly developed series, 6-oxo-5,6-dihydro-4H-benzo[f]pyrrolo[1,2-a][1,4]diazepin-9-yl-6-phenylhexylcarbamate (5 h) and 4-oxo-5,6-dihydro-4H-benzo[f]pyrrolo[1,2-a][1,4]diazepin-9-yl-(6-phenylhexyl)carbamate (5 i) (nanomolar FAAH inhibitors, the latter of which also shows micromolar affinity at the CB1R), were selected for further studies. Results of cell-based studies on a neuroblastoma cell line (IMR32) demonstrated 5 h, 5 i, and our reference compound 3 ([3-(3-carbamoylpyrrol-1-yl)phenyl] N-(5-phenylpentyl)carbamate) to lack any cytotoxic effect, while all three showed the ability to decrease oxidative stress by reducing the expression of the redox-sensitive transcription factor NF-κB. Encouraged by these data, these compounds were studied in vivo and were dosed orally in a mouse model of neuropathic pain. At 10 mg kg?1 all the compounds were able to relieve the hypersensitivity induced by oxaliplatin.