33543-55-4

Basic information

• Product Name: p-Nitrophenoxyamine
• Synonyms: p-Nitrophenoxyamine;O-(4-nitrophenyl)hydroxylaMine;O-(4-Nitrophenyl)
• CAS NO: 33543-55-4
• Molecular Formula: C₆H₆N₂O₃
• Molecular Weight: 154.124
• EINECS: 1312995-182-4
• Mol File: 33543-55-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 126-127℃
• Boiling Point: 313.246 °C at 760 mmHg
• Flash Point: 143.246 °C
• Appearance: /
• Density: 1.371 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.598
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.32±0.70(Predicted)
• CAS DataBase Reference: p-Nitrophenoxyamine(CAS DataBase Reference)
• NIST Chemistry Reference: p-Nitrophenoxyamine(33543-55-4)
• EPA Substance Registry System: p-Nitrophenoxyamine(33543-55-4)

Safety Data

• Hazardous Substances Data: 33543-55-4(Hazardous Substances Data)

Usage

General Description

p-Nitrophenoxyamine is a chemical compound that is commonly used as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, dyes, and pesticides. It is a yellowish crystalline solid with a molecular formula of C6H4N2O3. p-Nitrophenoxyamine is known for its combustion and explosive properties, making it a potential hazard in terms of safety if mishandled. It has been studied for its toxicological effects, particularly its potential to cause skin irritation and eye damage. Overall, p-Nitrophenoxyamine is an important chemical in the production of various industrial and commercial products, but its handling and use should be done with caution and adherence to safety protocols.

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

Synthetic route

ethyl O-(4-nitrophenyl)acetohydroxamate (83077-00-3) → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
Stage #1: ethyl O-(4-nitrophenyl)acetohydroxamate With hydrogenchloride; water at 25 - 32℃; for 1h; Stage #2: With sodium hydroxide In water at 33℃; Product distribution / selectivity;	99.9%
Stage #1: ethyl O-(4-nitrophenyl)acetohydroxamate With hydrogenchloride; water at 25 - 32℃; for 1.83333h; Stage #2: With sodium hydroxide In water at 33℃;	99.9%
Stage #1: ethyl O-(4-nitrophenyl)acetohydroxamate With hydrogenchloride; water In acetonitrile at 25 - 30℃; for 2h; Stage #2: With sodium hydroxide In water; acetonitrile	94%

4-nitro-phenol (100-02-7) + O-(p-nitrophenyl)benzohydroximoyl chloride (344266-15-5) → p-nitrophenoxyamine (33543-55-4) + p-nitrophenylbenzoate (959-22-8)

Conditions	Yield
With antimonypentachloride In benzene at 180℃; for 5h;	A 73% B 80 % Chromat.

N-(4'-nitrophenyloxy)-5-norborene-2,3-dicarboximide → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
With hydrazine hydrate In dichloromethane Substitution; Heating;	72%

C11H11F3N2O4 → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
With hydrogenchloride; water at 20℃; for 2.83333h; Sonication;	72%

4-nitro-phenol (100-02-7) → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
Stage #1: 4-nitro-phenol With potassium tert-butylate In methanol Stage #2: With mesitylenesulfonylhydroxylamine In N,N-dimethyl-formamide at 0℃; for 0.5h;	57%
Stage #1: 4-nitro-phenol With sodium methylate In methanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: With mesitylenesulfonylhydroxylamine In dichloromethane at 0℃; for 1h; Inert atmosphere; Cooling with ice;

4-Fluoronitrobenzene (350-46-9) → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
Stage #1: 4-Fluoronitrobenzene With tert-Butyl N-hydroxycarbamate; potassium hydroxide In ethanol at 23 - 60℃; for 72h; Inert atmosphere; Stage #2: With trifluoroacetic acid In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 23℃;	52%
Multi-step reaction with 2 steps 1: 92 percent / K2CO3 / dimethylformamide / 50 °C 2: 72 percent / hydazine monohydrate / CH2Cl2 / Heating View Scheme
Multi-step reaction with 2 steps 1: 53 percent / potassium hydroxide / ethanol / 6 h / Ambient temperature 2: 41 percent / trifluoromethanesulfonic acid / dioxane; H2O / 4 h / Ambient temperature View Scheme

ethyl O-(4-nitrophenyl)acetohydroxamate (83077-00-3) → 4-nitro-phenol (100-02-7) + p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
With hydrogenchloride; water at 20℃; for 2.33333h; Sonication;	A n/a B 50%

N-(4-nitrophenoxy)pyridinium tetrafluoroborate → 4-nitro-phenol (100-02-7) + p-nitrophenoxyamine (33543-55-4) + p-nitrophenylbenzoate (959-22-8) + 5-nitro-2-phenylbenzo[d]oxazole (891-43-0)

Conditions	Yield
With benzonitrile at 180℃; for 72h;	A 26.5% B n/a C 13% D 35%

N-(4-nitrophenoxy)pyridinium tetrafluoroborate + benzonitrile (100-47-0) → 4-nitro-phenol (100-02-7) + p-nitrophenoxyamine (33543-55-4) + p-nitrophenylbenzoate (959-22-8) + 5-nitro-2-phenylbenzo[d]oxazole (891-43-0)

Conditions	Yield
at 180℃; for 72h; Further byproducts given;	A 26.5% B n/a C 13% D 35%

N-(4-nitrophenoxy)pyridinium tetrafluoroborate + benzonitrile (100-47-0) → p-nitrophenoxyamine (33543-55-4) + p-nitrophenylbenzoate (959-22-8) + 5-nitro-2-phenylbenzo[d]oxazole (891-43-0) + benzamide (55-21-0)

Conditions	Yield
at 180℃; for 72h; Further byproducts given;	A n/a B 13% C 35% D 0.032 g

N-Boc-O-(4-nitrophenyl)hydroxylamine (33543-54-3) → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
With trifluoroacetic acid
With trifluoroacetic acid In dichloromethane

O-(p-nitrophenyl)benzohydroximoyl chloride (344266-15-5) → p-nitrophenoxyamine (33543-55-4) + p-nitrophenylbenzoate (959-22-8)

Conditions	Yield
With 4-nitro-phenol; antimonypentachloride In benzene at 180℃; for 5h;	A 73 % Chromat. B 80 % Chromat.

p-nitrophenyl benzohydroxamate (41828-26-6) → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 3 h / Heating 2: 73 percent Chromat. / p-nitrophenol, SbCl5 / benzene / 5 h / 180 °C View Scheme

methoxybenzene (100-66-3) + (+-)-<4-methoxy-phenyl>-succinic acid-anhydride → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 25.4 percent / 5 h / 180 °C 2: 73 percent / SbCl5 / benzene / 5 h / 180 °C View Scheme

4-chlorobenzonitrile (100-00-5) → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / t-BuOK / dimethylformamide / 0.5 h / 0 °C 2: 70 percent / HClO4 / H2O / 2 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: potassium hydroxide / N,N-dimethyl-formamide / 24 h / 10 - 20 °C 2: hydrogenchloride / acetonitrile; water / 2 h / 20 °C 3: sodium hydroxide / water; dichloromethane View Scheme

4-chlorobenzonitrile (100-00-5) → 4-nitro-phenol (100-02-7) + p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / N,N-dimethyl-formamide / 30 - 42 °C / Sonication 2: hydrogenchloride; water / 2.33 h / 20 °C / Sonication View Scheme

5-chloro-2-nitrotrifluoromethylbenzene (118-83-2) → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / N,N-dimethyl-formamide / 1.5 h / 30 °C / Sonication 2: hydrogenchloride; water / 2.83 h / 20 °C / Sonication View Scheme

C15H12N2O5 → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
With methanol; hydrazine hydrate In chloroform at 20℃;

O-(4-nitrophenyl)hydroxylamine hydrochloride → p-nitrophenoxyamine (33543-55-4)

Conditions	Yield
With sodium hydroxide In dichloromethane; water	45.5 g

p-nitrophenoxyamine (33543-55-4) + acetone (67-64-1) → propan-2-one O-(4-nitrophenyl)oxime (13680-03-0)

Conditions	Yield
With trifluoroacetic acid In ethanol at 20℃;	100%

p-nitrophenoxyamine (33543-55-4) + acetophenone (98-86-2) → 1-phenylethan-1-one O-(4-nitrophenyl) oxime (16237-47-1)

Conditions	Yield
With trifluoroacetic acid In ethanol at 20℃;	100%

p-nitrophenoxyamine (33543-55-4) + 1-ethoxy-2,2-difluoroethanol (148992-43-2) → C8H6F2N2O3

Conditions	Yield
at 50℃; for 24h; Sealed tube; Acidic conditions;	93%

p-nitrophenoxyamine (33543-55-4) + benzaldehyde (100-52-7) → (E)-benzaldehyde O-(4-nitrophenyl)oxime (75735-30-7)

Conditions	Yield
In ethanol at 20℃;	90%
With hydrogenchloride In ethanol Heating;

1-(4-hydroxy-phenyl)-heptane-1,3-dione (1137261-89-2) + p-nitrophenoxyamine (33543-55-4) → 1-(4-hydroxyphenyl)heptane-1,3-dione-3-[O-(4-nitrophenyl)oxime] (1137261-95-0)

Conditions	Yield
With acetic acid at 20℃; for 3h; Product distribution / selectivity;	88%

1-(4-hydroxy-phenyl)-heptane-1,3-dione (1137261-89-2) + p-nitrophenoxyamine (33543-55-4) → 1-(4-hydroxy-phenyl)-heptane-1,3-dione 3-[O-(4-nitro-phenyl)-oxime] (1253293-38-7)

Conditions	Yield
In acetic acid at 20℃; for 3h; Product distribution / selectivity;	88%
With acetic acid at 20℃; Industry scale;	88%
With acetic acid In dichloromethane at 20℃; for 16h; Product distribution / selectivity;	85%
With acetic acid In water at 0℃; for 0.25h; Product distribution / selectivity;
In dichloromethane at 20℃; for 16h; Product distribution / selectivity;

1-(4-hydroxy-phenyl)-heptane-1,3-dione (1137261-89-2) + p-nitrophenoxyamine (33543-55-4) → 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran (141645-16-1)

Conditions	Yield
With acetic acid at 70 - 100℃; for 25h; Product distribution / selectivity;	80%
In acetic acid at 70 - 100℃; for 25h; Product distribution / selectivity;	80%
With acetic acid at 70 - 100℃; for 17h; Product distribution / selectivity;	80%
With hydrogen bromide; acetic acid at 20℃; for 1h;

2,4-dinitrobenzaldehyde (528-75-6) + p-nitrophenoxyamine (33543-55-4) → (E)-O-p-nitrophenyl-2,4-dinitrobenzaldoxime

Conditions	Yield
With hydrogenchloride Condensation;	70%
With hydrogenchloride In water	68%

1-(4-methoxyphenyl)-1,3-heptanedione (1137261-90-5) + p-nitrophenoxyamine (33543-55-4) → (2-butyl-5-nitrobenzofuran-3-yl)(4-methoxyphenyl)methanone (141627-42-1)

Conditions	Yield
With acetic acid at 70 - 100℃; for 17h;	70%
With acetic acid at 70 - 100℃; for 17h; Product distribution / selectivity;	70%

2,4,6-trinitrobenzaldehyde (606-34-8) + p-nitrophenoxyamine (33543-55-4) → C13H7N5O9 (1334065-25-6)

Conditions	Yield
With hydrogenchloride	68%

2,2,2-trifluoro-1,1-ethanediol (421-53-4) + p-nitrophenoxyamine (33543-55-4) → C8H5F3N2O3

Conditions	Yield
at 60℃; for 24h; Sealed tube; Acidic conditions;	67%

1-cyclopropyl-6,7-difluoro-8-methoxyquinazoline-2,4(1H,3H)-dione (351367-87-8) + p-nitrophenoxyamine (33543-55-4) → 3-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1H-quinazoline-2,4-dione (351368-41-7) + C18H15FN4O6

Conditions	Yield
Stage #1: 1-cyclopropyl-6,7-difluoro-8-methoxyquinazoline-2,4(1H,3H)-dione With sodium hydride In 1,4-dioxane; N,N-dimethyl-formamide; mineral oil at 2 - 72℃; Stage #2: p-nitrophenoxyamine In 1,4-dioxane; N,N-dimethyl-formamide; mineral oil at 72℃; for 20h; Reagent/catalyst; Temperature; Time;	A 65% B n/a

1-(4-benzyloxyphenyl)-heptane-1,3-dione (1137261-88-1) + p-nitrophenoxyamine (33543-55-4) → 2-n-butyl-3-(4-hydroxybenzoyl)-5-nitrobenzofuran (141645-16-1)

Conditions	Yield
With hydrogen bromide; acetic acid at 20℃; for 6h; Product distribution / selectivity;	59%

1-cyclopropyl-6,7-difluoro-8-methoxyquinazoline-2,4(1H,3H)-dione (351367-87-8) + p-nitrophenoxyamine (33543-55-4) → 3-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1H-quinazoline-2,4-dione (351368-41-7)

Conditions	Yield
With potassium carbonate In 1,4-dioxane; N,N-dimethyl-formamide at 70 - 72℃; for 20h;	57%

(3E)-4-phenyl-3-buten-1-ol (937-58-6, 20047-19-2, 770-36-5) + p-nitrophenoxyamine (33543-55-4) → (2R*,3S*)-2-phenyltetrahydrofuran-3-amine

Conditions	Yield
Stage #1: (3E)-4-phenyl-3-buten-1-ol; p-nitrophenoxyamine In 2,2,2-trifluoroethanol for 0.25h; Inert atmosphere; Stage #2: With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In 2,2,2-trifluoroethanol at 20 - 65℃; for 76.5h; Inert atmosphere;	55%

p-nitrophenoxyamine (33543-55-4) + methoxybenzene (100-66-3) → 4-nitro-phenol (100-02-7) + 2-methoxy-phenylamine (90-04-0) + 4-methoxy-aniline (104-94-9)

Conditions	Yield
trifluoroacetic acid at 35 - 40℃; for 20h; Mechanism;	A 49% B 2.5% C 2.5%

p-nitrophenoxyamine (33543-55-4) → potassium N-nitro-O-(4-nitrophenyl)hydroxylaminide

Conditions	Yield
With potassium nitrite; iodosylbenzene In methanol at 0℃; for 0.166667h;	41%

Indole-3-carboxaldehyde (487-89-8) + p-nitrophenoxyamine (33543-55-4) → 1H-indole-3-carbaldehyde O-(4-nitrophenyl)oxime

Conditions	Yield
In ethanol at 20℃;	40%

p-nitrophenoxyamine (33543-55-4) + 4-chlorobenzaldehyde (104-88-1) → O-(4-Nitrophenyl)-4-chlorbenzaldoxim (38100-36-6)

Upstream product

• 33543-54-3 N-Boc-O-(4-nitrophenyl)hydroxylamine 
• 100-02-7 4-nitro-phenol 
• 344266-15-5 O-(p-nitrophenyl)benzohydroximoyl chloride 
• 83077-00-3 ethyl O-(4-nitrophenyl)acetohydroxamate 
• 100-47-0 benzonitrile 
• 350-46-9 4-Fluoronitrobenzene 
• 41828-26-6 p-nitrophenyl benzohydroxamate 
• 100-66-3 methoxybenzene 
• 100-00-5 4-chlorobenzonitrile 
• 118-83-2 5-chloro-2-nitrotrifluoromethylbenzene 

Downstream Products

• 38100-36-6 O-(4-Nitrophenyl)-4-chlorbenzaldoxim 
• 75735-27-2 E-O-p-nitrophenyl-p-nitrobenzaldoxime 
• 75735-30-7 (E)-benzaldehyde O-(4-nitrophenyl)oxime 
• 100-02-7 4-nitro-phenol 
• 90-04-0 2-methoxy-phenylamine 
• 104-94-9 4-methoxy-aniline 
• 83076-99-7 N-(4'-nitrophenoxy)-4-methylbenzenesulfonamide 
• 64584-52-7 (5S,8R,9S,10S,13S,14S,17R)-17-Ethynyl-17-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one O-(4-nitro-phenyl)-oxime 

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