4926-55-0

Basic information

• Product Name: 2-Nitro-N-hydroxyethyl aniline
• Synonyms: 2-[(2-nitrophenyl)amino]-ethano;Ethanol,2-[(2-nitrophenyl)amino]-;N-(2-HYDROXYETHYL)-2-NITROANILINE;2-[(2-NITROPHENYL)AMINO]ETHANOL;2-NITRO-N-(HYDROXYETHYL)ANILINE;2-NITRO-N-(2-HYDROXYETHYL)ANILINE;HC YELLOW NO 2;hc-yelow 2
• CAS NO: 4926-55-0
• Molecular Formula: C₈H₁₀N₂O₃
• Molecular Weight: 182.18
• EINECS: 225-555-8
• Product Categories: Intermediates of Dyes and Pigments;Electronic Chemicals
• Mol File: 4926-55-0.mol
• Article Data: 25

Chemical Properties

• Melting Point: 71-73°C
• Boiling Point: 376.6 °C at 760 mmHg
• Flash Point: 181.6 °C
• Appearance: Orange crystal powder
• Density: 1.352 g/cm³
• Vapor Pressure: 2.43E-06mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.60±0.10(Predicted)
• Water Solubility: 1.85g/L at 20℃
• CAS DataBase Reference: 2-Nitro-N-hydroxyethyl aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitro-N-hydroxyethyl aniline(4926-55-0)
• EPA Substance Registry System: 2-Nitro-N-hydroxyethyl aniline(4926-55-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 4926-55-0(Hazardous Substances Data)

Usage

Uses

2-(2-Nitroanilino)ethanol is used in the preparation of (phenylamino)quinoxalinone derivatives which has been identified as a new class of glycogen phosphorylase inhibitors.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C8H10N2O3/c11-6-5-9-7-3-1-2-4-8(7)10(12)13/h1-4,9,11H,5-6H2

Synthetic route

ethanolamine (141-43-5) + ortho-nitrofluorobenzene (1493-27-2) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
With potassium carbonate In ethanol for 5h; Reflux;	99%
In dimethyl sulfoxide for 1h; Ambient temperature;	98%
With potassium carbonate In butan-1-ol Reflux;	98%

ethanolamine (141-43-5) + 2-Chloronitrobenzene (88-73-3) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
at 100℃; for 3h; Substitution;	95.2%

2-amino-ethanol hydrochloride (2002-24-6) + ortho-nitrofluorobenzene (1493-27-2) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
With potassium carbonate In acetonitrile at 82℃; for 6h;	89%

2-nitrobenzenesulfonic acid (80-82-0) + ethanolamine (141-43-5) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
In dimethyl sulfoxide at 150℃; for 12h; Green chemistry;	74%

2-nitrophenyl bromide (577-19-5) + ethanolamine (141-43-5) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
at 100℃; for 8h;	68%
With potassium carbonate In butan-1-ol Heating;	54%
With copper dichloride
With copper dichloride
With potassium carbonate In ethanol for 8h; Reflux;

1-amino-2-(2-nitrophenoxy)ethane hydrochloride (98395-65-4) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0) + 8-nitro-3,4-dihydro-2H-1,4-benzoxazine (98395-66-5)

Conditions	Yield
With sodium hydroxide; 3,5-dinitrobenzoic acid at -10 - 6℃; for 4h;	A 18% B 57%

2-Chloronitrobenzene (88-73-3) + 2,2'-iminobis[ethanol] (111-42-2) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0) + N,N-bis(2-hydroxyethyl)-2-nitroaniline (7334-82-9) + 2-Chloroaniline (95-51-2) + 2,2'-dichloroazobenzene (7334-33-0, 49795-06-4, 63213-02-5)

Conditions	Yield
at 180℃; for 3h;	A 4.6% B 11% C 46% D 0.6%

1-amino-2-(2-nitrophenoxy)ethane hydrochloride (98395-65-4) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
With sodium hydroxide at 33℃;
With sodium hydroxide at 33℃; Rate constant;
With sodium hydroxide at 33℃; Rate constant; thermal Smiles rearrangement;

N-(2-hydroxy-ethyl)-2-nitro-benzenesulfonamide (18226-11-4) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
With sodium hydroxide

N-(2-ortho-nitrophenoxyethyl)phthalimide (98395-64-3) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / aq. HCl / acetic acid / 16 h / Heating 2: 0.01 M aq. NaOH / 33 °C / thermal Smiles rearrangement View Scheme
Multi-step reaction with 2 steps 1: 71 percent / aq. HCl / acetic acid / 16 h / Heating 2: 18 percent / aq. NaOH, 3,5-dinitrobenzoic acid / 4 h / -10 - 6 °C View Scheme

2-nitro-aniline (88-74-4) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
With potassium hydroxide In ethanol; water

2-Chloroethyl chloroformate (627-11-2) + 2-nitro-aniline (88-74-4) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
With hydrogenchloride; potassium hydroxide; sulfuric acid; calcium carbonate In anhydrous ethylene glycol dimethyl ether; water

2-nitro-aniline (88-74-4) + 2-chloro-ethanol (107-07-3) → 2-[(2-nitrophenyl)amino]ethanol (4926-55-0)

Conditions	Yield
In water at 80℃; for 8h; Green chemistry;

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 2-((2-hydroxyethyl)amino)aniline (4926-58-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol; water at 25℃; for 2h; Inert atmosphere;	100%
With hydrogen; palladium on activated charcoal In ethanol for 0.5h; Ambient temperature;	97%
With 5%-palladium/activated carbon; ammonium formate In methanol at 0 - 25℃; for 1h;	92%

5,5-dihydroxy-pyrimidine-2,4,6-trione (3237-50-1) + 2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 10-(2-hydroxyethyl)isoalloxazine (15800-90-5)

Conditions	Yield
Stage #1: 2-[(2-nitrophenyl)amino]ethanol With palladium 10% on activated carbon; hydrogen In methanol for 0.666667h; Stage #2: 5,5-dihydroxy-pyrimidine-2,4,6-trione With boric acid In acetic acid at 20 - 80℃; for 19h; Darkness;	92%

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) + methanesulfonyl chloride (124-63-0) → 2-((2-nitrophenyl)amino)ethyl methanesulfonate (100418-37-9)

Conditions	Yield
With pyridine Ambient temperature;	91%
With pyridine at 20℃; for 2h; Inert atmosphere; Cooling with ice;	76%
In pyridine; (2S)-N-methyl-1-phenylpropan-2-amine hydrate

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 2-nitro-aniline (88-74-4)

Conditions	Yield
With ammonium hydroxide; sodium sulfite In methanol at 70℃; for 144h;	80%

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9) + 2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 1,10-ethyleneisoalloxazinium chloride

Conditions	Yield
Stage #1: 2-[(2-nitrophenyl)amino]ethanol With palladium 10% on activated carbon; ammonium formate In methanol at 0 - 20℃; for 1h; Stage #2: pyrimidine-2,4,5,6(1H,3H)-tetraone With boric acid; acetic acid at 50℃; for 18h; Darkness; Stage #3: With thionyl chloride at 50℃; for 18h; Darkness;	80%

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) + p-toluenesulfonyl chloride (98-59-9) → 2-((2-nitrophenyl)amino)ethyl 4-methylbenzenesulfonate (1206187-50-9)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere;	75%

ethyl bromide (74-96-4) + 2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → N-(β-ethoxyethyl)-o-nitroaniline (95893-88-2)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 30 - 35℃; Alkylation;	55.5%

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) + propargyl bromide (106-96-7) → 2-nitrophenyl-(2-prop-2-ynyloxyethyl)amine (1252886-10-4)

Conditions	Yield
Stage #1: 2-[(2-nitrophenyl)amino]ethanol With sodium hydride In tetrahydrofuran; mineral oil at -20℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran; toluene; mineral oil at 20℃;	55%

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 4-(2-hydroxy-ethyl)-1,3-diphenyl-1,4-dihydro-cyclopenta[b]quinoxalin-2-one

Conditions	Yield
With acetic acid; zinc Erwaermen der Reaktionsloesung mit 3,5-Diphenyl-1,2,4-trion in Aethanol;

iodobenzene (591-50-4) + 2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 2-nitro-N-(2-phenoxyethyl)aniline (103748-27-2)

Conditions	Yield
With triphenyl phosphite; potassium carbonate 1.) reflux, 6 h; 2.) reflux, 1 h; Yield given. Multistep reaction;

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 1,2,3,4-tetrahydroquinoxaline (3476-89-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd/C 2: 30 percent / K2CO3; [Cp*IrCl2]2 / xylene / 120 h / 140 °C View Scheme
Multi-step reaction with 2 steps 1: Na2S2; H2O 2: concentrated aqueous HCl / 150 - 160 °C View Scheme

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 1-(2-hydroxy-ethyl)-1,4-dihydro-quinoxaline-2,3-dione (869199-14-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Pd/C / ethanol / 2585.74 Torr View Scheme

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 3-chloro-1-(2-hydroxy-ethyl)-1H-quinoxalin-2-one (869199-19-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2 / Pd/C / ethanol / 2585.74 Torr 2: phosphorous oxychloride / dimethylformamide / 95 °C View Scheme

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 4-[4-(2-hydroxy-ethyl)-3-oxo-3,4-dihydro-quinoxalin-2-ylamino]-N-thiophen-2-ylmethyl-benzamide

Conditions	Yield
Multi-step reaction with 4 steps 1: H2 / Pd/C / ethanol / 2585.74 Torr 2: phosphorous oxychloride / dimethylformamide / 95 °C 3: acetonitrile / 80 °C View Scheme

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 10-(2-hydroxyethyl)isoalloxazine (15800-90-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / HCOONH4 / Pd/C / methanol / 25 °C 2: boric acid / acetic acid / 1 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: 5%-palladium/activated carbon; ammonium formate / methanol / 1 h / 0 - 25 °C 2: boric acid; acetic acid / 1 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: ammonium formate; palladium on activated charcoal / methanol / 1 h / 0 °C 2: boric acid; acetic acid / 50 °C View Scheme

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 1,10-ethyleneisoalloxazinium chloride

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / HCOONH4 / Pd/C / methanol / 25 °C 2: boric acid / acetic acid / 1 h / 50 °C 3: SOCl2 / 16 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: 5%-palladium/activated carbon; ammonium formate / methanol / 1 h / 0 - 25 °C 2: boric acid; acetic acid / 1 h / 50 °C / Inert atmosphere 3: thionyl chloride / 16 h / 50 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: ammonium formate; palladium on activated charcoal / methanol / 1 h / 0 °C 2: boric acid; acetic acid / 50 °C 3: thionyl chloride / 20 h / 50 °C View Scheme

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 1,10-ethano-5-acetyl-1,5-dihydrolumiflavin

Conditions	Yield
Multi-step reaction with 4 steps 1: 91 percent / HCOONH4 / Pd/C / methanol / 25 °C 2: boric acid / acetic acid / 1 h / 50 °C 3: SOCl2 / 16 h / 50 °C 4: 54 percent / Zn / trifluoroacetic acid / 1 h / Heating View Scheme

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → N-(β-ethoxyethyl)-o-phenylenediamine (95893-89-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 55.5 percent / NaH in oil / dimethylformamide / 30 - 35 °C 2: Zn; HCl View Scheme

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 1-(2-ethoxyethyl)-2-chloro-1H-benzimidazole (87233-54-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 55.5 percent / NaH in oil / dimethylformamide / 30 - 35 °C 2: Zn; HCl 3: Heating 4: POCl3 View Scheme

Upstream product

• 577-19-5 2-nitrophenyl bromide 
• 141-43-5 ethanolamine 
• 88-73-3 2-Chloronitrobenzene 
• 1493-27-2 ortho-nitrofluorobenzene 
• 80-82-0 2-nitrobenzenesulfonic acid 
• 2002-24-6 2-amino-ethanol hydrochloride 
• 88-74-4 2-nitro-aniline 
• 107-07-3 2-chloro-ethanol 
• 627-11-2 2-Chloroethyl chloroformate 
• 98395-64-3 N-(2-ortho-nitrophenoxyethyl)phthalimide 
• 18226-11-4 N-(2-hydroxy-ethyl)-2-nitro-benzenesulfonamide 
• 111-42-2 2,2'-iminobis[ethanol] 
• 98395-65-4 1-amino-2-(2-nitrophenoxy)ethane hydrochloride 

Downstream Products

• 4926-58-3 2-((2-hydroxyethyl)amino)aniline 
• 88-74-4 2-nitro-aniline 
• 15800-90-5 10-(2-hydroxyethyl)isoalloxazine 
• 24134-25-6 2-(2-amino-1H-benzo[d]imidazole-1-yl)ethan-1-ol 
• 102000-86-2 2-[2-(hydroxymethyl)-1H-benzimidazol-1-yl]ethanol 
• 4946-06-9 2-(2-phenyl-1H-benzo[d]imidazol-1-yl)ethanol 
• 1252886-10-4 2-nitrophenyl-(2-prop-2-ynyloxyethyl)amine 
• 114853-42-8 1,10-ethyleneisoalloxazinium chloride 
• 1206187-50-9 2-((2-nitrophenyl)amino)ethyl 4-methylbenzenesulfonate 
• 91-19-0 2,3-diethynylquinoxaline 
• 100417-25-2 2-imino-3-(2'-nitrophenyl)-thiazolidine hydrochloride 
• 100418-44-8 2-nitro-N-(2-thiocyanatoethyl)-aniline 
• 103748-28-3 N-(2-Nitro-phenyl)-N-(2-phenoxy-ethyl)-acetamide 
• 147362-14-9 <1-<2-<(p-tolylsulfonyl)oxy>ethyl>-2-benzimidazolidinylidene>propanedinitrile 

Relevant articles and documents

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Discovery and development of 2-aminobenzimidazoles as potent antimalarials

The emergence of Plasmodium falciparum resistance to frontline antimalarials, including artemisinin combination therapies, highlights the need for new molecules that act via novel mechanisms of action. Herein, we report the design, synthesis and antimalarial activity of a series of 2-aminobenzimidazoles, featuring a phenol moiety that is crucial to the pharmacophore. Two potent molecules exhibited IC50 values against P. falciparum 3D7 strain of 42 ± 4 (3c) and 43 ± 2 nM (3g), and high potency against strains resistant to chloroquine (Dd2), artemisinin (Cam3.IIC580Y) and PfATP4 inhibitors (SJ557733), while demonstrating no cytotoxicity against human cells (HEK293, IC50 > 50 μM). The most potent molecule, possessing a 4,5-dimethyl substituted phenol (3r) displayed an IC50 value of 6.4 ± 0.5 nM against P. falciparum 3D7, representing a 12-fold increase in activity from the parent molecule. The 2-aminobenzimidazoles containing a N1-substituted phenol represent a new class of molecules that have high potency in vitro against P. falciparum malaria and low cytotoxicity. They possessed attractive pharmaceutical properties, including low molecular weight, high ligand efficiency, high solubility, synthetic tractability and low in vitro clearance in human liver microsomes.

A green and practical reduction of N-(4-chlorophenyl)-2-nitroaniline and its derivatives to corresponding N-substituted-benzene-1,2-diamines using thiourea dioxide

A new effective approach for synthesizing diverse N-substituted-benzene-1,2-diamines is reported. The treatment of N-substituted-2-nitroanilines with thiourea dioxide in the presence of sodium hydroxide efficiently formed the corresponding N-substituted-benzene-1,2-diamines, including N-(4-chlorophenyl)benzene-1,2-diamine with a good yield of 94%. The by-product is environmentally-friendly urea and is easy to separate from the product by filtration procedure that enhances the convenience of the approach.