99-57-0

Basic information

• Product Name: 2-Amino-4-nitrophenol
• Synonyms: nci-c55958;p-nitroaminofenol;rodol42;2-Amino-4-nitrophenol;2-Hydroxy-5-nitroaniline; 3-Amino-4-hydroxynitrobenzene;6-Hydroxy-3-Nitroaniline;2-AMINO-4-NITROPHENOL OEKANAL, 250 MG;4 NAP (4 NITRO 2 AMINO PHENOL);Phenol, 2-amino-4-nitro-
• CAS NO: 99-57-0
• Molecular Formula: C₆H₆N₂O₃
• Molecular Weight: 154.12
• EINECS: 202-767-9
• Product Categories: Intermediates of Dyes and Pigments;Aromatic Phenols;Phenoles and thiophenoles;Amines;Aromatics;Intermediates & Fine Chemicals;Mutagenesis Research Chemicals;Pharmaceuticals;dye intermediates
• Mol File: 99-57-0.mol
• Article Data: 33

Chemical Properties

• Melting Point: 140-143 °C(lit.)
• Boiling Point: 322.46°C (rough estimate)
• Flash Point: 100 °C
• Appearance: ochre crystalline powder
• Density: 1.3617 (estimate)
• Vapor Pressure: 6.17E-06mmHg at 25°C
• Refractive Index: 1.6890 (rough estimate)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.82±0.22(Predicted)
• Water Solubility: slightly soluble
• BRN: 776533
• CAS DataBase Reference: 2-Amino-4-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-nitrophenol(99-57-0)
• EPA Substance Registry System: 2-Amino-4-nitrophenol(99-57-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-68-43-40-20/21/22
• Safety Statements: 26-45-36/37/39-36
• RIDADR: 2811
• WGK Germany: 2
• RTECS: SJ6300000
• TSCA: Yes
• Hazardous Substances Data: 99-57-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 99-57-0 differently. You can refer to the following data:
1. An aromatic constituent found in hair dyes and other cosmetic products with very low levels of mutagenic activity.
2. 2-Amino-4-nitrophenol is used in preparing some mordant dyes and in some hair dyes.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 82, 1955The Journal of Organic Chemistry, 45, p. 4992, 1980 DOI: 10.1021/jo01312a039

General Description

Orange prisms or yellow powder. No odor.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Oxidation of 2-Amino-4-nitrophenol may occur in the presence of air and violent decomposition may occur if 2-Amino-4-nitrophenol is allowed to dry out completely at elevated temperatures. 2-Amino-4-nitrophenol is stable when stored protected from light and under nitrogen for two weeks at temperatures up to 140° F, and storage under nitrogen for up to 24 weeks at room temperature (77° F) should produce no loss of stability. 2-Amino-4-nitrophenol is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. 2-Amino-4-nitrophenol is also incompatible with iron.

Fire Hazard

Flash point data for 2-Amino-4-nitrophenol are not available. 2-Amino-4-nitrophenol is probably combustible.

Flammability and Explosibility

Nonflammable

Purification Methods

Crystallise the phenol from water. [Beilstein 13 IV 896.]

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

Synthetic route

2,4-Dinitrophenol (51-28-5) → 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With hydrazine hydrate at 90℃; for 18h;	98%
With hydrazine hydrate In water at 110℃; Sealed tube; Green chemistry;	95%
With hydrazine hydrate In isopropyl alcohol at 110℃; for 0.25h; Catalytic behavior; Sealed tube; chemoselective reaction;	94%

sodium 2,4-dinitrophenoxide (1011-73-0) → 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen at 70℃; under 4500.45 Torr; for 2h; Temperature; Pressure; Time; Autoclave;	97.1%

C6H7BN2O4 (1604034-83-4) → 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With iron(III) oxide; oxygen In tetrahydrofuran at 20℃; Irradiation;	95%

2,4-Dinitrophenol (51-28-5) → 4-amino-2-nitrophenol (119-34-6) + 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With nickel; hydrazine hydrate In ethanol; 1,2-dichloro-ethane at 50 - 60℃; for 4h;	A 7% B 92%
With hydrogen; iron; acetic acid; palladium dichloride In ethanol at 20 - 25℃; under 258.6 - 2327.2 Torr;	A n/a B 79%
With sodium hydroxide; sodium disulfide
With sodium sulfide; 5-hydroxynaphtho-1,4-quinone; water In methanol; phosphate buffer for 12h; pH=2.5; Reduction;

2-amino-phenol (95-55-6) → 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 3h;	92%
Multi-step reaction with 2 steps 2: HNO3+H2SO4 / <0 / beim Kochen des Reaktionsprodukts mit Salzsaeure View Scheme
With sulfuric acid; nitric acid In chloroform at 8 - 12℃; Solvent; Temperature; Large scale;	830 kg

2-azido-4-nitrophenol (33354-58-4) → 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With ammonium hydroxide at 90℃; for 2.41667h;	78%

1-phenyl-2-(piperidin-1-yl)ethanone O-(2,4-dinitrophenyl)oxime → 2,4-Dinitrophenol (51-28-5) + 2-hydroxy-5-nitroaniline (99-57-0) + 2-Phenyl-5,6,7,8-tetrahydro-imidazo<1,2-a>pyridin (3649-46-5)

Conditions	Yield
In dimethyl sulfoxide at 25℃; for 5h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;	A 33% B 22% C 75%

4-Nitrophenylene-1,2-diamine (99-56-9) → 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With water; sodium hydroxide at 100℃; for 4h;	65%

2-amino-phenol (95-55-6) → 2-amino-6-nitrophenol (603-87-2) + 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With sulfuric acid; aminosulfonic acid; nitric acid at 0℃; for 0.5h;	A 26% B 44%

6-fluoro-3-nitroaniline (369-36-8) → 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With sodium hydroxide for 72h; Heating;	30%

2-methyl-1,3-benzoxazole (95-21-6) → 2-hydroxy-5-nitroaniline (99-57-0) + 2-Amino-5-nitrophenol (121-88-0)

Conditions	Yield
With sulfuric acid; nitric acid beim Kochen des Reaktionsprodukts mit Salzsaeure;

3-nitrophenyl azide (1516-59-2) → 4-amino-2-nitrophenol (119-34-6) + 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With sulfuric acid

2,4-Dinitrophenol (51-28-5) + hydrogen sulfide (7783-06-4) + ammonia (7664-41-7) → 2-hydroxy-5-nitroaniline (99-57-0)

2,4-Dinitrophenol (51-28-5) + alkaline aqueous Na2S → 2-hydroxy-5-nitroaniline (99-57-0)

2,4-Dinitrophenol (51-28-5) + water (7732-18-5) + hydrogen + nickel → 2-hydroxy-5-nitroaniline (99-57-0)

2,4-Dinitrophenol (51-28-5) + water (7732-18-5) + sulfur dioxide + iron turnings → 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
at 80 - 90℃;

2,4-Dinitrophenol (51-28-5) + vanadium compound → 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
bei der elektrolytischen Reduktion;

m-nitro-diazobenzeneimide → 4-amino-2-nitrophenol (119-34-6) + 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
With sulfuric acid

sulfuric acid (7664-93-9) + 3-nitrophenyl azide (1516-59-2) → 4-amino-2-nitrophenol (119-34-6) + 2-hydroxy-5-nitroaniline (99-57-0)

para-methoxynitrobenzene (100-17-4) → 4-methoxy-aniline (104-94-9) + 2-hydroxy-5-nitroaniline (99-57-0) + 3-amino-4-methoxynitrobenzene (99-59-2)

Conditions	Yield
With 3,5-dinitrobenzoic acid; ammonia In water-d2; acetonitrile UV-irradiation;

2-hydroxynitrobenzene (88-75-5) → 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: Na2S2O4; NaOH-solution / <30 3: HNO3+H2SO4 / <0 / beim Kochen des Reaktionsprodukts mit Salzsaeure View Scheme

2,4-Dinitrophenol (51-28-5) → 4-nitro-phenol (100-02-7) + 1,2-dihydroxy-4-nitrobenzene (3316-09-4) + C6H4N2O4 + C12H8N4O7 + 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
In isopropyl alcohol Mechanism; Irradiation;

1-chloro-2,4-dinitro-benzene (97-00-7) → 2,4-Dinitrophenol (51-28-5) + 2-hydroxy-5-nitroaniline (99-57-0)

Conditions

Yield

Multi-step reaction with 5 steps 1: triethylamine / acetone / 25 °C / Inert atmosphere 2: hydrazine hydrate / methanol; dichloromethane / 8 h / 0 °C / Inert atmosphere 3: hydrogenchloride / ethanol / 25 °C / Inert atmosphere 4: sodium carbonate / dichloromethane / 2 h / 25 °C / Inert atmosphere 5: dimethyl sulfoxide / 5 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube; Irradiation View Scheme

2-(2,4-dinitrophenoxy)-1H-isoindole-1,3(2H)-dione (60506-35-6) → 2,4-Dinitrophenol (51-28-5) + 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate / methanol; dichloromethane / 8 h / 0 °C / Inert atmosphere 2: hydrogenchloride / ethanol / 25 °C / Inert atmosphere 3: sodium carbonate / dichloromethane / 2 h / 25 °C / Inert atmosphere 4: dimethyl sulfoxide / 5 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube; Irradiation View Scheme

O-(2,4-dinitrophenyl)hydroxylamine (17508-17-7) → 2,4-Dinitrophenol (51-28-5) + 2-hydroxy-5-nitroaniline (99-57-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol / 25 °C / Inert atmosphere 2: sodium carbonate / dichloromethane / 2 h / 25 °C / Inert atmosphere 3: dimethyl sulfoxide / 5 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube; Irradiation View Scheme

2-bromo-1-phenylethanone O-(2,4-dinitro-phenyl)oxime → 2,4-Dinitrophenol (51-28-5) + 2-hydroxy-5-nitroaniline (99-57-0) + 2-Phenyl-5,6,7,8-tetrahydro-imidazo<1,2-a>pyridin (3649-46-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate / dichloromethane / 2 h / 25 °C / Inert atmosphere 2: dimethyl sulfoxide / 5 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube; Irradiation View Scheme

2-amino-6-nitrophenol (603-87-2) → 2-hydroxy-5-nitroaniline (99-57-0) + 2-Amino-5-nitrophenol (121-88-0)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: triethylamine / 1,2-dichloro-ethane / 65 - 75 °C / Large scale 2.1: hydrogen; platinum on activated charcoal / 1,2-dichloro-ethane / 55 - 65 °C / 4500.45 - 6000.6 Torr / Large scale 3.1: sulfuric acid; sodium nitrite; copper(II) sulfate / isopropyl alcohol; ethyl acetate / Heating; Large scale 4.1: sulfuric acid; nitric acid / dichloromethane / 35 - 45 °C / Large scale 4.2: 100 - 105 °C / 1125.11 - 1875.19 Torr / pH 8 / Large scale View Scheme

2,6-dinitrophenol (573-56-8) → 2-hydroxy-5-nitroaniline (99-57-0) + 2-Amino-5-nitrophenol (121-88-0)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: palladium on activated charcoal; hydrogen / 1,2-dichloro-ethane / 35 - 40 °C / 1500.15 - 4500.45 Torr / Large scale 2.1: triethylamine / 1,2-dichloro-ethane / 65 - 75 °C / Large scale 3.1: hydrogen; platinum on activated charcoal / 1,2-dichloro-ethane / 55 - 65 °C / 4500.45 - 6000.6 Torr / Large scale 4.1: sulfuric acid; sodium nitrite; copper(II) sulfate / isopropyl alcohol; ethyl acetate / Heating; Large scale 5.1: sulfuric acid; nitric acid / dichloromethane / 35 - 45 °C / Large scale 5.2: 100 - 105 °C / 1125.11 - 1875.19 Torr / pH 8 / Large scale View Scheme

4-nitrobenzo[d]oxazol-2(3H)-one (28955-71-7) → 2-hydroxy-5-nitroaniline (99-57-0) + 2-Amino-5-nitrophenol (121-88-0)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: hydrogen; platinum on activated charcoal / 1,2-dichloro-ethane / 55 - 65 °C / 4500.45 - 6000.6 Torr / Large scale 2.1: sulfuric acid; sodium nitrite; copper(II) sulfate / isopropyl alcohol; ethyl acetate / Heating; Large scale 3.1: sulfuric acid; nitric acid / dichloromethane / 35 - 45 °C / Large scale 3.2: 100 - 105 °C / 1125.11 - 1875.19 Torr / pH 8 / Large scale View Scheme

chloroacetyl chloride (79-04-9) + 2-hydroxy-5-nitroaniline (99-57-0) → 6-nitro-4H-benzo[1,4]oxazin-3-one (81721-87-1)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%
With sodium hydrogencarbonate In water; 4-methyl-2-pentanone at 0℃; Heating / reflux;	100%
Stage #1: 2-hydroxy-5-nitroaniline With sodium hydrogencarbonate In water at 0℃; for 0.5h; Stage #2: chloroacetyl chloride In water Reflux;	95%

2-hydroxy-5-nitroaniline (99-57-0) + 4-methoxyphenyl-acetic chloride (4693-91-8) → N-(2-hydroxy-5-nitro-phenyl)-2-(4-methoxy-phenyl)-acetamide

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃; for 2h;	100%

chloranil (118-75-2) + 2-hydroxy-5-nitroaniline (99-57-0) → 8-nitro-1,2,4-trichloro-3H-phenoxazin-3-one (32624-06-9)

Conditions	Yield
With sodium acetate In ethanol for 24h;	99%
With sodium acetate In ethanol
With ethanol; sodium acetate at 25℃;

1,1'-carbonyldiimidazole (530-62-1) + 2-hydroxy-5-nitroaniline (99-57-0) → 5-nitro-3H-benzooxazol-2-one (3889-13-2)

Conditions	Yield
In tetrahydrofuran for 2h; Reflux;	99%
In tetrahydrofuran for 3h; Reflux;	99%
In dichloromethane at 20℃; for 24h; Inert atmosphere;	96%

trifluoroacetic anhydride (407-25-0) + 2-hydroxy-5-nitroaniline (99-57-0) → N-(2'-hydroxy-5'-nitrophenyl)trifluoroacetamide (170363-62-9)

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 16h;	99%

furfural (98-01-1) + 2-hydroxy-5-nitroaniline (99-57-0) → 2-(2'-furylmethyl)amino-4-nitrophenol (890657-56-4)

Conditions	Yield
With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃;	98%

2,5-hexanedione (110-13-4) + 2-hydroxy-5-nitroaniline (99-57-0) → 1-(2’-hydroxy-5’-nitrophenyl)-2,5-dimethyl-1H-pyrrole

Conditions	Yield
With Cl(1-)*C5H14NO(1+)*3ZnCl2 In neat (no solvent) for 0.166667h; Paal-Knorr Pyrrole Synthesis; Sealed tube; Sonication; Green chemistry;	98%
With MIL-53(Al) In neat (no solvent) at 80℃; for 0.25h; Paal-Knorr Pyrrole Synthesis; Sonication;	98%
With nano-Fe3O4 immoblized lewis acidic ionic liquid In neat (no solvent) at 20℃; for 0.75h; Paal-Knorr Pyrrole Synthesis; Sonication;	63%

1,12-dodecanedioyl dichloride (4834-98-4) + 2-hydroxy-5-nitroaniline (99-57-0) → C24H30N4O8

Conditions	Yield
With lithium chloride In 1-methyl-pyrrolidin-2-one; water; isopropyl alcohol at 20℃; for 1h; Inert atmosphere; Cooling with ice;	98%

benzaldehyde (100-52-7) + 2-hydroxy-5-nitroaniline (99-57-0) → 2-hydroxy-5-nitro-N-benzylideneaniline (3230-49-7)

Conditions	Yield
In methanol for 1h;	97.2%
In water at 140℃; for 3.5h; Temperature; High pressure;	64.5%

formic acid (64-18-6) + 2-hydroxy-5-nitroaniline (99-57-0) → N-(2-hydroxy-5-nitrophenyl)formamide (70886-35-0)

Conditions	Yield
Stage #1: formic acid With acetic anhydride at 70℃; for 2h; Stage #2: 2-hydroxy-5-nitroaniline In tetrahydrofuran at 20℃; for 3h;	97%
Stage #1: formic acid With acetic anhydride at 70℃; for 2h; Stage #2: 2-hydroxy-5-nitroaniline In tetrahydrofuran at 20℃; for 3h;	97%
With sodium formate for 2.5h; Heating;	94%
With pyridine; acetic anhydride at 20℃; for 18h;

butyryl chloride (141-75-3) + 2-hydroxy-5-nitroaniline (99-57-0) → N-(2'-hydroxy-5'-nitrophenyl)butyramide (199929-62-9)

Conditions	Yield
With pyridine In tetrahydrofuran Heating;	97%
With pyridine In tetrahydrofuran for 60h; Heating;	97%
With 4-methyl-morpholine In dichloromethane at 0℃; for 0.5h;	72%

potassium ethyl xanthogenate (140-89-6) + 2-hydroxy-5-nitroaniline (99-57-0) → 2-mercapto-5-nitrobenzo[d]oxazole (22876-21-7)

Conditions	Yield
With hydrogenchloride In ethanol	97%
In ethanol for 12h; Reflux;	97%
In methanol for 6h; Reflux;	94%

2,2'-dipyridyl carbonate (1659-31-0) + 2-hydroxy-5-nitroaniline (99-57-0) → 5-nitro-3H-benzooxazol-2-one (3889-13-2)

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	96%

tris(tert-butylthio)cyclopropenylium perchlorate + 2-hydroxy-5-nitroaniline (99-57-0) → (Z)-2-<1',2',-bis(tert-butylthio)vinyl>-5-nitrobenzoxazole (124552-85-8)

Conditions	Yield
In methanol for 2h; Ambient temperature;	96%

benzoyl chloride (98-88-4) + 2-hydroxy-5-nitroaniline (99-57-0) → 5-nitro-2-phenylbenzo[d]oxazole (891-43-0)

Conditions	Yield
With Al-Cu-Cl- hydrotalcite at 60℃; for 1h;	96%
Heating;	94%
In 1,4-dioxane at 210℃; for 0.25h; microwave;	90%

acetic anhydride (108-24-7) + 2-hydroxy-5-nitroaniline (99-57-0) → 2-methyl-5-nitro-1,3-benzoxazole (32046-51-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 100℃; Acetylation; cyclization;	96%
With toluene-4-sulfonic acid In toluene at 50 - 120℃; for 3h;
Stage #1: acetic anhydride; 2-hydroxy-5-nitroaniline In toluene for 1h; Reflux; Stage #2: With toluene-4-sulfonic acid In toluene for 5h; Dean-Stark;	8 g

2-hydroxy-5-nitroaniline (99-57-0) + S-tert-butyl cyclohexylcarbamoylthioacetate (339274-36-1) → N-cyclohexyl-malonamic acid 2-(2-cyclohexylcarbamoyl-acetylamino)-4-nitro-phenyl ester

Conditions	Yield
With silver trifluoroacetate In tetrahydrofuran at 20℃;	96%

2-hydroxy-5-nitroaniline (99-57-0) + 2,4-Dihydroxybenzaldehyde (95-01-2) → 4-{(E)-[(2-hydroxy-5-nitrophenyl)imino]methyl}benzene-1,3-diol

Conditions	Yield
In methanol at 20℃;	96%

oxalic acid diethyl ester (95-92-1) + 2-hydroxy-5-nitroaniline (99-57-0) → 5-nitrobenzo[d]oxazole-2-carboxylic acid ethyl ester

Conditions	Yield
With sodium docusate In water at 60℃; for 2.5h; Reagent/catalyst;	96%

acetic anhydride (108-24-7) + 2-hydroxy-5-nitroaniline (99-57-0) → 2-acetamido-4-nitrophenol (97-60-9)

Conditions	Yield
In water at 60℃;	95%
With toluene-4-sulfonic acid In toluene at 100℃;	82%
for 0.00277778h; Green chemistry;	56%
With acetic acid
at 25℃;

potassium ethyl xanthogenate (140-89-6) + 2-hydroxy-5-nitroaniline (99-57-0) → 4-nitro-1,3-benzoaxazolidine-2-thione (22876-21-7)

Conditions	Yield
With acetic acid In ethanol for 4.5h; pH=5; Reflux;	95%
In ethanol Reflux;	95%
In pyridine at 120℃; for 16h;	84%
Stage #1: potassium ethyl xanthogenate; 2-hydroxy-5-nitroaniline In pyridine for 1h; Heating / reflux; Stage #2: With hydrogenchloride In pyridine; water	79%

butyryl chloride (141-75-3) + 2-hydroxy-5-nitroaniline (99-57-0) → 2-butyrylamino-4-nitrophenylbutanoate (477559-71-0)

Conditions	Yield
With triethanolamine In CH2C2; dichloromethane	95%

orthoformic acid triethyl ester (122-51-0) + 2-hydroxy-5-nitroaniline (99-57-0) → 5-nitro-benzooxazole (70886-33-8)

Conditions	Yield
at 160℃; for 4h;	95%
With 1,1'-((ethane-1,2-diylbis(oxy))bis(ethane-2,1-diyl))bis(3-propyl-1H-imidazol-3-ium) bromide In neat (no solvent) for 0.333333h; Heating;	92%
at 150℃; for 6h;	85%

titanium(IV) isopropylate (546-68-9) + salicylaldehyde (90-02-8) + 2-hydroxy-5-nitroaniline (99-57-0) → Ti(C6H3(NO2)(O)NCHC6H4(O))2 (104453-12-5)

Conditions	Yield
byproducts: (CH3)2CHOH, H2O; extn. (THF); elem. anal.;	94.4%

(Z)-2-hydroxy-4-oxo-4-phenylbut-2-enoic acid (103344-70-3) + 2-hydroxy-5-nitroaniline (99-57-0) → (Z)-6-nitro-3-(2-oxo-2-phenylethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one

Conditions	Yield
In isopropyl alcohol for 2.5h; Heating;	94%

4-chlorobenzoyl chloride (586-75-4) + 2-hydroxy-5-nitroaniline (99-57-0) → 2-(4-bromophenyl)-5-nitro-1,3-benzoxazole (112606-72-1)

Conditions	Yield
In 1,4-dioxane at 210℃; for 0.25h; microwave;	94%
Stage #1: 4-chlorobenzoyl chloride; 2-hydroxy-5-nitroaniline In 1,4-dioxane at 210℃; for 0.25h; Irradiation; Stage #2: With sodium hydroxide In 1,4-dioxane; water at 20℃;

benzaldehyde (100-52-7) + 2-hydroxy-5-nitroaniline (99-57-0) → 5-nitro-2-phenylbenzo[d]oxazole (891-43-0)

Conditions	Yield
With tin dioxide In ethanol at 20℃; for 0.216667h; Green chemistry;	94%
In neat (no solvent) at 140℃; for 6h;	90%
Stage #1: benzaldehyde; 2-hydroxy-5-nitroaniline In m-xylene at 120℃; for 0.5h; Inert atmosphere; Stage #2: With oxygen; 4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical In m-xylene at 120℃; for 10h;	89%

Upstream product

• 51-28-5 2,4-Dinitrophenol 
• 369-36-8 6-fluoro-3-nitroaniline 
• 606-21-3 1-chloro-2,6-dinitrobenzene 
• 59-49-4 2-Benzoxazolinone 
• 81900-93-8 4-amino-2-benzoxazolone 
• 28955-71-7 4-nitrobenzo[d]oxazol-2(3H)-one 
• 573-56-8 2,6-dinitrophenol 
• 603-87-2 2-amino-6-nitrophenol 
• 17508-17-7 O-(2,4-dinitrophenyl)hydroxylamine 
• 60506-35-6 2-(2,4-dinitrophenoxy)-1H-isoindole-1,3(2H)-dione 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 1011-73-0 sodium 2,4-dinitrophenoxide 
• 1604034-83-4 C₆H₇BN₂O₄ 
• 99-56-9 4-Nitrophenylene-1,2-diamine 

Downstream Products

• 32624-06-9 8-nitro-1,2,4-trichloro-3H-phenoxazin-3-one 
• 137592-35-9 benzoic acid-(2-hydroxy-5-nitro-anilide) 
• 875876-02-1 carbamoylsulfanyl-acetic acid-(2-hydroxy-5-nitro-anilide) 
• 35588-39-7 N-Chloracetyl-4-nitro-2-amino-phenol 
• 31039-95-9 4-Nitro-2-phenylazo-phenol 
• 52829-25-1 2,9-dinitro-triphenodioxazine 
• 4008-48-4 nitroxoline 
• 97-60-9 2-acetamido-4-nitrophenol 
• 3889-13-2 5-nitro-3H-benzooxazol-2-one 
• 1433-78-9 glyoxal-bis-(2-hydroxy-5-nitro-phenylimine) 
• 78749-98-1 5-nitro-N-phenyl-1,3-benzoxazol-2-amine 
• 74032-78-3 N-(2-hydroxyethyl)-2-hydroxy-5-nitroaniline 
• 22876-21-7 4-nitro-1,3-benzoaxazolidine-2-thione 
• 856633-95-9 2-hydroxy-5-nitro-benzenediazonium betaine 

Relevant articles and documents

Ferredoxin-stimulated photoreduction of 2,4-dinitrophenol with solubilized chlorophyll a.

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A Common, Facile and Eco-Friendly Method for the Reduction of Nitroarenes, Selective Reduction of Poly-Nitroarenes and Deoxygenation of N-Oxide Containing Heteroarenes Using Elemental Sulfur

A transition metal-free, environment-friendly and practical protocol was developed either for the reduction of nitroarenes or for the deoxygenation of N-oxide containing heteroarenes. The reaction proceeded with the use of a non-toxic and cheap feedstock as elemental sulfur in aqueous methanol under relatively mild conditions. Green chemistry credentials were widely favorable compared to traditional and industrial protocols with good E-factors and a low production of waste. The strategy allowed the efficient reduction of a large variety of substituted-nitroarenes including various o-nitroanilines as well as selective reduction of various poly-nitroarenes in excellent yields with a broad substrate scope. The protocol was successfully extended to the deoxygenation of some N-oxide containing heteroarenes, like benzofuroxans, phenazine N,N'-dioxides, pyridine N-oxides, 2H-indazole N1-oxides, quinoxaline N1,N4-dioxides and benzo[d]imidazole N1,N3-dioxides. A gram-scale example for the synthesis of luminol, in green conditions, was reported. A solid mechanism of reaction was proposed from experimental evidences.

Method for synthesizing benzoxazole compound by using nitration by-products of aromatic hydrocarbon and application of benzoxazole compound

The invention discloses a method for synthesizing a benzoxazole compound by using nitration by-products of aromatic hydrocarbon and application of the benzoxazole compound. The method comprises the main process: performing step-by-step crystallization on nitration products of a 2,4-dinitrochlorobenzene production enterprise so as to obtain 2,4-dinitrochlorobenzene, 2,6-dinitrochlorobenzene (I) anda small amount of residues, adopting the obtained 2,6-dinitrochlorobenzene (I) as the main starting material, and performing hydrolysis, selective catalytic hydrogenation reduction, cyclization, halogenation, carbon-carbon coupling and other processes so as to synthesize the benzoxazole compound, wherein the obtained compound can be used as a main raw material to synthesize a series of chemical intermediates with important application, and the chemical intermediates include o-aminophenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol and hydrochloride of o-aminophenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol. Through the method, the industrial by-products are converted into high value-added aromatic aminophenol products, industrial hazardous waste of the 2,4-dinitrochlorobenzene production enterprise is reduced, the scope of products of the enterprise is widened, and the economic benefits of enterprise are increased.