Product Name

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  • Name

    4-Nitroaniline

  • EINECS 202-810-1
  • CAS No. 100-01-6
  • Article Data828
  • CAS DataBase
  • Density 1.333 g/cm3
  • Solubility 0.8 g/L (20 °C) in water
  • Melting Point 147 °C
  • Formula C6H6N2O2
  • Boiling Point 333.1 °C at 760 mmHg
  • Molecular Weight 138.126
  • Flash Point 165 °C
  • Transport Information UN 1661
  • Appearance Yellow solid with a mild odor
  • Safety 28-36/37-45-61-28A-16-1/2-7
  • Risk Codes 23/24/25-33-52/53-39/23/24/25-11
  • Molecular Structure Molecular Structure of 100-01-6 (4-Nitroaniline)
  • Hazard Symbols ToxicT,FlammableF
  • Synonyms Aniline,p-nitro- (8CI);1-Amino-4-nitrobenzene;4-Amino-1-nitrobenzene;4-Aminonitrobenzene;4-Nitro-1-aminobenzene;
  • PSA 71.84000
  • LogP 2.28140

Synthetic route

para-dinitrobenzene
100-25-4

para-dinitrobenzene

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With formic acid In acetonitrile at 20℃; for 1h; Irradiation;100%
In water at 25℃; for 0.333333h; Sonication;99%
With sodium tetrahydroborate In water at 95℃; for 0.333333h; Green chemistry;98%
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; tetrabutylammonium perchlorate In N,N-dimethyl-formamide electrolytic reduction at a Pt gauze electrode at a potential of -0.30 V;100%
With Decaborane; palladium on activated charcoal In methanol at 20℃; for 0.25h;99%
With triethylsilane; indium(III) chloride In acetonitrile at -20℃; for 0.25h;99%
(4-nitro-phenyl)-m-tolyl sulfone
77853-01-1

(4-nitro-phenyl)-m-tolyl sulfone

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

Toluene-3-thiosulfonic acid; compound with ammonia
77853-09-9

Toluene-3-thiosulfonic acid; compound with ammonia

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;A 43%
B 100%
C 40%
...Expand
1-methoxy-4-((4-nitrophenyl)sulfonyl)benzene
22865-57-2

1-methoxy-4-((4-nitrophenyl)sulfonyl)benzene

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

4-Methoxy-benzenethiosulfonic acid; compound with ammonia
77853-03-3

4-Methoxy-benzenethiosulfonic acid; compound with ammonia

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;A 56%
B 100%
C 32%
With sulfur; ammonia at 100℃; for 2h; Product distribution; titanium autoclave; various reactions temp. and amounts of S8;
...Expand
p-nitrophenyl isocyanide
1984-23-2

p-nitrophenyl isocyanide

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With graphitic carbon nitride; hydrazine hydrate In water at 70℃; for 8h; Time; Darkness; Sealed tube; Green chemistry; chemoselective reaction;100%
4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With ammonium hydroxide at 120 - 190℃; under 45004.5 - 46504.7 Torr; for 4h; Temperature; Pressure;99.31%
With ammonium hydroxide; copper(l) iodide at 200℃; for 6.5h; Reagent/catalyst; Temperature; Time; Autoclave; Green chemistry;97%
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 4h;96%
tert-butyl N-(4-nitrophenyl)carbamate
18437-63-3

tert-butyl N-(4-nitrophenyl)carbamate

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With EPZG clay In dichloromethane for 1.5h; deacylation; Heating;99%
With H-β zeolite In dichloromethane for 4h; Heating;98%
With water at 150℃; for 10h; Subcritical conditions;97%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; Kinetics; liquid NH3;99%
With ammonium hydroxide; copper(l) iodide; phosphate potassium salt In N,N-dimethyl-formamide at 20℃; for 36h; Inert atmosphere;98%
Stage #1: p-nitrobenzene iodide With copper(l) iodide; D-glucosamine hydrochloride; potassium carbonate In water; acetone at 90℃; for 0.166667h;
Stage #2: With ammonia In water; acetone at 90℃; for 28h;		98%
para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
Stage #1: para-nitrophenyl bromide With copper(l) iodide; D-glucosamine hydrochloride; potassium carbonate In water; acetone at 90℃; for 0.166667h;
Stage #2: With ammonia In water; acetone at 90℃; for 28h;		98%
With ammonium hydroxide at 20℃; for 3h; Catalytic behavior;98%
With ammonia; triethylamine In water at 20℃; for 2.5h;98%
L-methionine
63-68-3

L-methionine

3,5-dinitro-1-(4-nitrophenyl)-4-pyridone
74197-40-3

3,5-dinitro-1-(4-nitrophenyl)-4-pyridone

A

4-nitro-aniline
100-01-6

4-nitro-aniline

B

(S)-2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-4-methylsulfanyl-butyric acid
92782-41-7

(S)-2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-4-methylsulfanyl-butyric acid

Conditions
ConditionsYield
In pyridine; water for 3h; Ambient temperature;A n/a
B 98%
...Expand
α-naphthol
90-15-3

α-naphthol

4'-nitrobenzenesulfenanilide
64168-52-1

4'-nitrobenzenesulfenanilide

A

2-phenylthio-1-naphthol
68143-73-7

2-phenylthio-1-naphthol

B

4-(phenylthio)naphthalen-1-ol
19133-53-0

4-(phenylthio)naphthalen-1-ol

C

4-nitro-aniline
100-01-6

4-nitro-aniline

D

2,4-bis(phenylthio)naphthalen-1-ol
103929-98-2

2,4-bis(phenylthio)naphthalen-1-ol

Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 0.166667h; Ambient temperature; Further byproducts given;A 42%
B 33%
C 98%
D 10%
...Expand
α-naphthol
90-15-3

α-naphthol

4'-nitrobenzenesulfenanilide
64168-52-1

4'-nitrobenzenesulfenanilide

A

2-phenylthio-1-naphthol
68143-73-7

2-phenylthio-1-naphthol

B

4-(phenylthio)naphthalen-1-ol
19133-53-0

4-(phenylthio)naphthalen-1-ol

C

4-nitro-aniline
100-01-6

4-nitro-aniline

D

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 0.166667h; Ambient temperature; Further byproducts given;A 42%
B 33%
C 98%
D 14%
...Expand
α-naphthol
90-15-3

α-naphthol

4'-nitrobenzenesulfenanilide
64168-52-1

4'-nitrobenzenesulfenanilide

A

2-phenylthio-1-naphthol
68143-73-7

2-phenylthio-1-naphthol

B

4-(phenylthio)naphthalen-1-ol
19133-53-0

4-(phenylthio)naphthalen-1-ol

C

4-nitro-aniline
100-01-6

4-nitro-aniline

D

2,4-bis(phenylthio)naphthalen-1-ol
103929-98-2

2,4-bis(phenylthio)naphthalen-1-ol

E

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With trifluoroacetic acid In benzene for 0.166667h; Product distribution; Mechanism; 1.5 eqiv. TFA;A 42%
B 33%
C 98%
D 10%
E 14%
...Expand
4'-nitrobenzenesulfenanilide
64168-52-1

4'-nitrobenzenesulfenanilide

A

S-Phenyl benzenethiosulfonate
1212-08-4

S-Phenyl benzenethiosulfonate

B

4-nitro-aniline
100-01-6

4-nitro-aniline

C

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With trifluoroacetic acid In benzene at 25℃; Product distribution; Mechanism; further sulfenanilide;A 32%
B 98%
C 56%
...Expand
trifluoroacetic acid
76-05-1

trifluoroacetic acid

S,S-di-n-butyl-N-(4-nitrophenyl)imino-λ4-sulfane

S,S-di-n-butyl-N-(4-nitrophenyl)imino-λ4-sulfane

A

butyl sulfoxide
2168-93-6

butyl sulfoxide

B

2,2,2-trifluoro-N-(4-nitrophenyl)acetamide
404-27-3

2,2,2-trifluoro-N-(4-nitrophenyl)acetamide

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
at 72℃; for 72h; Elimination; acylation; retro-Pummerer reaction;A 79%
B 98%
C 2%
...Expand
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With ammonium iodide; hydrazine hydrate In ethanol at 60℃; for 42h; Inert atmosphere; Sealed tube;97%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1h; Product distribution; Further Variations:; Solvents; reaction time; Heating;96%
With 40% potassium fluoride/alumina at 85℃; for 0.0666667h; Microwave irradiation; Neat (no solvent);94%
p-nitrobenzanilide
3393-96-2

p-nitrobenzanilide

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1.5h; Product distribution; Further Variations:; Solvents; reaction time; Heating;97%
In methanol
4-Nitro-N-phenylhydroxylamine
16169-16-7

4-Nitro-N-phenylhydroxylamine

C11H14N2O4
88867-70-3

C11H14N2O4

A

4-nitrosonitrobenzene
4485-08-9

4-nitrosonitrobenzene

B

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With iron(II) chloride In water; acetonitrile at 40℃; pH=4.7, ionic strength=0.5 M;A 39%
B 95%
With iron(II) chloride In water; acetonitrile at 40℃; Mechanism; pH=4.7, ionic strength=0.5 M;
...Expand
C11H14N2O4
88867-70-3

C11H14N2O4

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With iron(II) chloride In water; acetonitrile at 40℃; pH=4.7, ionic strength=0.5 M;95%
With FeCl2 or CuCl In water; acetonitrile at 40℃; Product distribution; Mechanism; pH=4.7, ionic strength=0.5 M;
3-methyl-1-(4-nitrophenyl)-5-nitrouracil
108047-30-9

3-methyl-1-(4-nitrophenyl)-5-nitrouracil

methylamine
74-89-5

methylamine

A

1,3-dimethyl-5-nitrouracil
41613-26-7

1,3-dimethyl-5-nitrouracil

B

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
In methanol for 0.5h; Ambient temperature;A 95%
B n/a
...Expand
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

diethyl malonate
105-53-3

diethyl malonate

A

1,3-diethyl 2-diazopropanedioate
5256-74-6

1,3-diethyl 2-diazopropanedioate

B

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With tetrabutylammonium perchlorate In N,N-dimethyl-formamide electrolytic reduction at a Pt gauze electrode at a potential of -0.30 V;A 95%
B 101 %
...Expand
ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate
78596-42-6

ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With ethylenediamine In ethanol at 20℃; for 2.3h;95%
pyridine
110-86-1

pyridine

3,5-dinitro-1-(4-nitrophenyl)-4-pyridone
74197-40-3

3,5-dinitro-1-(4-nitrophenyl)-4-pyridone

A

4-nitro-aniline
100-01-6

4-nitro-aniline

B

1-Hydroxy-3,5-dinitro-1H-pyridin-4-one; compound with pyridine
139055-63-3

1-Hydroxy-3,5-dinitro-1H-pyridin-4-one; compound with pyridine

Conditions
ConditionsYield
With hydroxylamine hydrochloride at 20℃; for 2h;A 94%
B 83%
...Expand
C14H13NO5S
77863-74-2

C14H13NO5S

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

3-Ethoxy-benzenethiosulfonic acid; compound with ammonia
77853-06-6

3-Ethoxy-benzenethiosulfonic acid; compound with ammonia

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;A 47%
B 94%
C 40%
...Expand
C11H14N2O4
88867-70-3

C11H14N2O4

N-(4-chlorophenyl)hydroxylamine
823-86-9

N-(4-chlorophenyl)hydroxylamine

A

1-chloro-4-nitroso-benzene
932-98-9

1-chloro-4-nitroso-benzene

B

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With iron(II) chloride In water; acetonitrile at 40℃; pH=4.7, ionic strength=0.5 M;A 53%
B 94%
With iron(II) chloride In water; acetonitrile at 40℃; Mechanism; pH=4.7, ionic strength=0.5 M;
...Expand
nitrobenzene
98-95-3

nitrobenzene

A

4-nitrosoaniline
659-49-4

4-nitrosoaniline

B

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With pyrene; tetramethyl ammoniumhydroxide; benzamide; potassium carbonate In dimethyl sulfoxide at 90℃; for 2.08333 - 2.16667h; Conversion of starting material;A 94%
B 6%
With potassium hydroxide; pyrene; potassium carbonate; urea In dimethyl sulfoxide at 90℃; for 2.08333 - 2.16667h; Conversion of starting material;A 87%
B 12%
With urea, monopotassium salt; urea In dimethyl sulfoxide at 90℃; for 2h;A 56%
B 5.5%
aniline
62-53-3

aniline

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With Vilsmeier reagent; potassium nitrate In neat (no solvent) at 100℃; under 1500.15 Torr; Reagent/catalyst; Temperature; Microwave irradiation;93%
With nitric acid; sodium dodecyl-sulfate In water at 25℃; for 0.333333h; Micellar solution; Green chemistry; regioselective reaction;86%
With nitric acid; sodium dodecyl-sulfate In acetonitrile at 24.84℃; for 3h; Micellar solution; regioselective reaction;85%
pyridine
110-86-1

pyridine

3,5-dinitro-1-(4-nitrophenyl)-4-pyridone
74197-40-3

3,5-dinitro-1-(4-nitrophenyl)-4-pyridone

A

4-nitro-aniline
100-01-6

4-nitro-aniline

B

4-aci-Nitro-4H-isoxazol-5-one; compound with pyridine

4-aci-Nitro-4H-isoxazol-5-one; compound with pyridine

Conditions
ConditionsYield
With hydroxylamine hydrochloride at 20℃; for 2h;A 93%
B 88%
...Expand
para-dinitrobenzene
100-25-4

para-dinitrobenzene

A

4-Nitro-N-phenylhydroxylamine
16169-16-7

4-Nitro-N-phenylhydroxylamine

B

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With 1,2-bis(mercaptomethyl)benzene; (Et4N) In acetonitrile at 26℃; for 1.5h;A 93%
B 2%
With D-glucose; bakers' yeast In phosphate buffer; ethanol at 30℃; for 0.5h; pH=6.5; Product distribution; Further Variations:; time;A 83%
B n/a
With sodium tetrahydroborate; selenium In ethanol at 23 - 26℃; for 0.25h;A 81%
B 16%
With 1,2-bis(mercaptomethyl)benzene; (Et4N) In acetonitrile at 26℃; for 1.5h; Product distribution;
1,3-Dichloro-5-(4-nitro-benzenesulfonyl)-benzene
77853-02-2

1,3-Dichloro-5-(4-nitro-benzenesulfonyl)-benzene

A

di(p-nitrophenyl) disulfide
100-32-3

di(p-nitrophenyl) disulfide

B

3,5-Dichloro-benzenethiosulfonic acid; compound with ammonia
77853-10-2

3,5-Dichloro-benzenethiosulfonic acid; compound with ammonia

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;A 42%
B 93%
C 40%
...Expand
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitro-aniline
100-01-6

4-nitro-aniline

N-(4-nitrobenzylidene)-4-nitroaniline
10480-05-4

N-(4-nitrobenzylidene)-4-nitroaniline

Conditions
ConditionsYield
at 60℃; for 2h;100%
at 83 - 85℃;100%
With sulfuric acid In neat (no solvent) Microwave irradiation; Sealed tube; Green chemistry;72%
benzaldehyde
100-52-7

benzaldehyde

4-nitro-aniline
100-01-6

4-nitro-aniline

4-nitro-N-(phenylmethylene)benzenamine
785-81-9, 1613-94-1, 40339-44-4

4-nitro-N-(phenylmethylene)benzenamine

Conditions
ConditionsYield
In toluene at 120℃; for 24h;100%
With aqueous extract of pericarp of Sapindus trifoliatus fruits at 20℃; for 0.0333333h;98%
sodium hydrogen sulfate; silica gel at 52 - 54℃; for 0.0222222h; microwave irradiation;95%
4-nitro-aniline
100-01-6

4-nitro-aniline

butyryl chloride
141-75-3

butyryl chloride

N-(4'-nitrophenyl)butyramide
54191-12-7

N-(4'-nitrophenyl)butyramide

Conditions
ConditionsYield
With NMM In dichloromethane100%
With triethylamine In dichloromethane at 20℃;71%
With sodium hydroxide; acetone
4-nitro-aniline
100-01-6

4-nitro-aniline

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-(4-nitrophenyl)-4-methylbenzenesulfonamide
734-25-8

N-(4-nitrophenyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 4℃;100%
With (Na1752K0.144Ca0365Mg0.065)(Al2044Si2774O96)*19.16H2O In ethanol at 25 - 30℃; for 2h; Sonication; Green chemistry;96%
With pyridine In dichloromethane at 20℃; for 12h;94%
4-nitro-aniline
100-01-6

4-nitro-aniline

2-chloropropionyl chloride
625-36-5

2-chloropropionyl chloride

3-chloro-N-(4-nitrophenyl)propanamide
19313-88-3

3-chloro-N-(4-nitrophenyl)propanamide

Conditions
ConditionsYield
at 0 - 50℃; Neat (no solvent);100%
at 20 - 50℃;100%
at 50℃; for 16h;97%
4-nitro-aniline
100-01-6

4-nitro-aniline

diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate
78596-42-6

ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate

Conditions
ConditionsYield
at 120℃; for 3h; Heating / reflux;100%
for 0.025h; Gould-Jacob reaction; Irradiation;98%
In ethanol at 28℃; for 6h;95%
4-nitro-aniline
100-01-6

4-nitro-aniline

p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

Conditions
ConditionsYield
With potassium iodide; 10-camphorsulfonic acid; sodium nitrite In acetic acid at 20℃; for 24h; Time;100%
With Nitrogen dioxide; sodium iodide In acetonitrile at -20℃; for 10h;98%
Stage #1: 4-nitro-aniline With toluene-4-sulfonic acid In water at 20℃;
Stage #2: With potassium iodide In water at 20℃; for 1.5h;		95%
4-nitro-aniline
100-01-6

4-nitro-aniline

4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

Conditions
ConditionsYield
Stage #1: 4-nitro-aniline With toluene-4-sulfonic acid; sodium nitrite In water at 20℃; for 0.333333h;
Stage #2: With sodium azide In water at 20℃; Reagent/catalyst;		100%
Stage #1: 4-nitro-aniline With trifluoroacetic acid; sodium nitrite In water at 0℃; for 0.166667h;
Stage #2: With sodium azide In water at 20℃; for 5h;		99%
Stage #1: 4-nitro-aniline With hydrogenchloride In water at 0℃;
Stage #2: With sodium nitrite In water for 0.166667h; Further stages;		99%
4-nitro-aniline
100-01-6

4-nitro-aniline

4-nitrobenzenediazonium chloride
100-05-0

4-nitrobenzenediazonium chloride

Conditions
ConditionsYield
With nitrosylchloride under 750.075 Torr; for 24h;100%
With sodium nitrite In hydrogenchloride; water at 0.2℃; Rate constant;
With hydrogenchloride; sodium nitrite In hydrogenchloride; water at 25℃; Rate constant;
4-nitro-aniline
100-01-6

4-nitro-aniline

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

Conditions
ConditionsYield
With t-butyl thionitrite; copper dichloride In acetonitrile at 25℃; for 2h;100%
With t-butyl thionitrite; copper dichloride In acetonitrile at 25℃; for 0.0333333h; Product distribution; Mechanism; var. temperature, var. time, other copper(II) halides, other reagents, other substituted aniline derivatives;98%
Stage #1: 4-nitro-aniline With tert.-butylnitrite In acetonitrile at 20℃; Sandmeyer Reaction; Flow reactor;
Stage #2: With copper dichloride In ethylene glycol; acetonitrile at 82℃; Sandmeyer Reaction; Flow reactor;		91%
4-nitro-aniline
100-01-6

4-nitro-aniline

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With palladium diacetate; carbon monoxide; triphenylphosphine In water; acetic acid at 56℃; under 532 Torr; for 11h;100%
With triethylsilane; palladium dichloride In ethanol at 20℃; for 1h; Inert atmosphere;100%
With 10% palladium on activated charcoal; hydrogen for 2h;100%
4-nitro-aniline
100-01-6

4-nitro-aniline

β-naphthol
135-19-3

β-naphthol

para red
6410-10-2

para red

Conditions
ConditionsYield
With potassium hydrogensulfate; water; sodium nitrite for 0.0333333h; Diazotization; coupling; microwave irradiation;100%
With hydrogenchloride; sodium nitrite In water at 20℃; for 1h; Time;99%
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.0833333h; Reagent/catalyst; Temperature; Green chemistry;99%
4-nitro-aniline
100-01-6

4-nitro-aniline

phenol
108-95-2

phenol

4-(4'-hydroxyphenylazo)nitrobenzene
1435-60-5, 81944-71-0

4-(4'-hydroxyphenylazo)nitrobenzene

Conditions
ConditionsYield
Stage #1: 4-nitro-aniline With hydrogenchloride; sodium nitrite In water at 2℃; for 1.5h;
Stage #2: phenol With sodium hydroxide In water at 2 - 20℃; for 4h;		100%
Stage #1: 4-nitro-aniline With carboxyl- and nitrite- functionalized graphene quantum dots at 20℃; for 0.0833333h;
Stage #2: phenol In water at 20℃; for 0.166667h;		96%
Stage #1: 4-nitro-aniline With hydrogenchloride In water; acetone at 0℃; Inert atmosphere;
Stage #2: With sodium nitrite In water; acetone at 0℃; for 1h; Inert atmosphere;
Stage #3: phenol With sodium carbonate; sodium hydroxide In water; acetone at 0 - 20℃; for 3h; Inert atmosphere;		92%
ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
3652-48-0

ethyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate

4-nitro-aniline
100-01-6

4-nitro-aniline

ethyl 5-methyl-3-(4-nitrophenylazo)-2-phenylpyrrole-4-carboxylate

ethyl 5-methyl-3-(4-nitrophenylazo)-2-phenylpyrrole-4-carboxylate

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate; sodium nitrite In acetic acid at 0℃; for 1h;100%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

4-nitro-aniline
100-01-6

4-nitro-aniline

N-(4-methoxybenzylidene)-4-nitroaniline
15450-66-5

N-(4-methoxybenzylidene)-4-nitroaniline

Conditions
ConditionsYield
With pyrrolidine In dichloromethane at 20℃; for 16h; Molecular sieve;100%
With TiO2 nanotubes at 20℃; for 8h; Neat (no solvent); Sunlight;98%
sodium hydrogen sulfate; silica gel at 64 - 66℃; for 0.025h; microwave irradiation;96%
6,7-dideoxy-α,β-D-galacto-hept-6-enopyranose
117452-48-9, 117475-50-0

6,7-dideoxy-α,β-D-galacto-hept-6-enopyranose

4-nitro-aniline
100-01-6

4-nitro-aniline

N-p-nitrophenyl-6,7-dideoxy-L-galacto-hept-6-enosylamine
128357-86-8

N-p-nitrophenyl-6,7-dideoxy-L-galacto-hept-6-enosylamine

Conditions
ConditionsYield
In methanol; acetic acid at 110℃; for 0.166667h;100%
4-nitro-aniline
100-01-6

4-nitro-aniline

phenylacetyl chloride
103-80-0

phenylacetyl chloride

N-(4-nitrophenyl)-2-phenylacetamide
13140-77-7

N-(4-nitrophenyl)-2-phenylacetamide

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 0 - 20℃; for 2h;100%
With potassium phosphate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;95%
In dichloromethane at 20℃; for 1h;70%
4-nitro-aniline
100-01-6

4-nitro-aniline

Acetic formic anhydride
2258-42-6

Acetic formic anhydride

p-nitroformanilide
16135-31-2

p-nitroformanilide

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 0.25h;100%
In tetrahydrofuran at 20℃; for 3h; Schlenk technique; Inert atmosphere;77%
In tetrahydrofuran
4-nitro-aniline
100-01-6

4-nitro-aniline

p-nitrobenzene diazonium nitrate

p-nitrobenzene diazonium nitrate

Conditions
ConditionsYield
With Nitrogen dioxide In 1,4-dioxane at 10 - 40℃;100%
With Nitrogen dioxide at 0℃; for 6h;92%
With Nitrogen dioxide; N,N-dimethyl-formamide In N,N-dimethyl-formamide for 0.0833333h;91%
With tributyl phosphate-NO2 In various solvent(s) at 10 - 15℃;90%
With polyethylene glycol - NO2 In various solvent(s)84%
dichloromethylenedimethyliminium chloride
33842-02-3, 529510-96-1

dichloromethylenedimethyliminium chloride

4-nitro-aniline
100-01-6

4-nitro-aniline

[Chloro-(4-nitro-phenylamino)-methylene]-dimethyl-ammonium; chloride

[Chloro-(4-nitro-phenylamino)-methylene]-dimethyl-ammonium; chloride

Conditions
ConditionsYield
at -20℃; for 1h; ball mill;100%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-nitro-aniline
100-01-6

4-nitro-aniline

(4-chlorobenzylidene)(4-nitrophenyl)amine
5340-14-7

(4-chlorobenzylidene)(4-nitrophenyl)amine

Conditions
ConditionsYield
for 36h; Ambient temperature;100%
In neat (no solvent) at 20℃; for 72h;80%
In ethanol for 2h; Reflux;76%
p-Anisaldehyde dimethyl acetal
2186-92-7

p-Anisaldehyde dimethyl acetal

4-methoxy-aniline
104-94-9

4-methoxy-aniline

4-nitro-aniline
100-01-6

4-nitro-aniline

(E)-N-(4-methoxybenzylidene)-4-nitroaniline
97221-15-3

(E)-N-(4-methoxybenzylidene)-4-nitroaniline

Conditions
ConditionsYield
In dichloromethane Condensation; Heating;100%
...Expand
acetophenone dimethyl acetal
4316-35-2

acetophenone dimethyl acetal

4-nitro-aniline
100-01-6

4-nitro-aniline

(4-nitrophenyl)(1-phenylethylidene)amine

(4-nitrophenyl)(1-phenylethylidene)amine

Conditions
ConditionsYield
In dichloromethane Condensation; Heating;100%
4-nitro-aniline
100-01-6

4-nitro-aniline

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

N-isopropylidene-4-nitro-aniline
22104-23-0

N-isopropylidene-4-nitro-aniline

Conditions
ConditionsYield
In dichloromethane Condensation; Heating;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

tert-butyl 4-aminobenzoate
18144-47-3

tert-butyl 4-aminobenzoate

4-nitro-aniline
100-01-6

4-nitro-aniline

1-(4'-nitrophenyl)-3-(4''-tert-butylcarboxyphenyl)urea
301317-92-0

1-(4'-nitrophenyl)-3-(4''-tert-butylcarboxyphenyl)urea

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; 4-nitro-aniline With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 0.833333h; Substitution;
Stage #2: tert-butyl 4-aminobenzoate In tetrahydrofuran at 20℃; for 42h; Substitution;		100%
...Expand
4-nitro-aniline
100-01-6

4-nitro-aniline

4-chloro-5-methoxy-2-methyl-2H-pyridazin-3-one
14628-57-0

4-chloro-5-methoxy-2-methyl-2H-pyridazin-3-one

5-methoxy-2-methyl-4-(4-nitro-phenylamino)-2H-pyridazin-3-one

5-methoxy-2-methyl-4-(4-nitro-phenylamino)-2H-pyridazin-3-one

Conditions
ConditionsYield
With potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene at 120℃; for 7h; Substitution; Amination;100%

4-Nitroaniline Specification

The 4-Nitroaniline with CAS registry number of 100-01-6 is also known as 1-Amino-4-nitrobenzene. The IUPAC name and product name are the same. It belongs to product categories of Anilines, Aromatic Amines and Nitro Compounds; Organics; Aniline; Functional Materials; Organic Nonlinear Optical Materials; NA - NI; Alpha Sort; Amines; AromaticsVolatiles/ Semivolatiles; Chemical Class; N; N-OAlphabetic; Analytical Standards; AromaticsChemical Class; NA - NIAnalytical Standards; Nitro Compounds; Indicators for non-aqueous titrationsTitration;Metal Titration Indicators; Indicators; Titration; I-N, Puriss p.a.Spectroscopy; Analytical Reagents for General Use; Mass Spectrometry (MS)&LC-MS; Puriss p.a.; Reagents for Mass Spectrometry (MS); C2 to C6Photonic and Optical Materials; NLO Chromophores and Intermediates; Non-Linear Optical (NLO) Materials; C2 to C6Stains and Dyes; Nitrogen Compounds; Stains&Dyes, A to. Its EINECS registry number is 202-810-1. In addition, the formula is C6H6N2O2 and the molecular weight is 138.12. This chemical is a yellow solid with a mild odor and should be sealed in ventilated, cool room away from fire and heat. Besides, it is slightly soluble in cold water, soluble in boiling water, ethanol, ether, benzene and acid.

Physical properties about 4-Nitroaniline are: (1)ACD/LogP: 1.20; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.195; (4)ACD/LogD (pH 7.4): 1.195; (5)ACD/BCF (pH 5.5): 4.769; (6)ACD/BCF (pH 7.4): 4.769; (7)ACD/KOC (pH 5.5): 106.469; (8)ACD/KOC (pH 7.4): 106.472; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.634; (13)Molar Refractivity: 37.034 cm3; (14)Molar Volume: 103.555 cm3; (15)Surface Tension: 60.318 dyne/cm; (16)Density: 1.334 g/cm3; (17)Flash Point: 165 °C; (18)Enthalpy of Vaporization: 57.588 kJ/mol; (19)Boiling Point: 333.051 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of 4-Nitroaniline: it is prepared by nitration, hydrolysis reaction of acetanilide.

C6H4ClNO2 + 2 NH3 → NH4Cl + C6H6N2O2

Uses of 4-Nitroaniline. This chemical is commonly used as an intermediate in the synthesis of dyes, antioxidants, pharmaceuticals and gasoline, in gum inhibitors, poultry medicines, and as a corrosion inhibitor. What's more, it can be used to produce 1-(4-nitro-phenyl)-pyrrole-2-carbaldehyde by reaction with furfural. The reaction occurs with reagent 2n-HCl and solution ethanol with other condition of heating for 2 hours. The yield is about 90%.

4-Nitroaniline can be used to produce 1-(4-nitro-phenyl)-pyrrole-2-carbaldehyde by reaction with furfural.

When you are using this chemical, please be cautious about it. As a chemical, it is harmful to aquatic organisms that may cause long-term adverse effects in the aquatic environment. Beside, it has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. Furthermore, it has danger of cumulative effects and it is highly flammable. During using it, wear suitable protective clothing, gloves and keep away from sources of ignition. In case of accident or if you feel unwell seek medical advice immediately. After contact with skin, wash immediately. Afer using it, keep container tightly closed, locked up and out of the reach of children. Avoid release to the environment.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC(=CC=C1N)[N+](=O)[O-]
2. InChI: InChI=1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2
3. InChIKey: TYMLOMAKGOJONV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 75mg/kg (75mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
guinea pig LD50 oral 450mg/kg (450mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Voprosy Kommunal'noi Gigieny. Problems of Communal Hygiene. Vol. 6, Pg. 89, 1966.
guinea pig LD50 skin > 500mg/kg (500mg/kg)   National Technical Information Service. Vol. OTS0572389,
mammal (species unspecified) LDLo intravenous 40mg/kg (40mg/kg) BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 34, 1941.
mouse LD50 intramuscular 800mg/kg (800mg/kg)   Igiena. Vol. 15, Pg. 151, 1966.
mouse LD50 intraperitoneal 250mg/kg (250mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 oral 810mg/kg (810mg/kg)   Toxicology and Applied Pharmacology. Vol. 42, Pg. 417, 1977.
quail LD50 oral 1gm/kg (1000mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
rat LD50 oral 750mg/kg (750mg/kg)   Ceskoslovenska Hygiena. Czechoslovak Hygiene. Vol. 23, Pg. 168, 1978.
rat LDLo intraperitoneal 600mg/kg (600mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 92, 1982.

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