100-01-6

Basic information

• Product Name: 4-Nitroaniline
• Synonyms: C.I. 37035; C.I. Azoic Diazo Component 37; C.I. Developer 17; p-Nitroaniline; fast red GG base; Para Nitro Aniline; Paranitroaniline; Azoic Diazo Component 37; 1-Amino-4-nitrobenzene; 4-nitroaniline hydrochloride (1:1); mercury bis[(4-nitrophenyl)azanide]; 4-Nitroaniline(NH2=1)
• CAS NO: 100-01-6
• Molecular Formula: C₆H₆N₂O₂
• Molecular Weight: 138.124
• EINECS: 202-810-1
• Product Categories: Aniline;Functional Materials;Organic Nonlinear Optical Materials;Anilines, Aromatic Amines and Nitro Compounds;Organics;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);amine | nitro-compound;Building Blocks;C6;Chemical Synthesis;Materials Science;Nitrogen Compounds;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;Organic and Printed Electronics;C2 to C6Stains and Dyes;Nitrogen Compounds;Stains&Dyes, A to;C2 to C6Photonic and Optical Materials;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;Organic Building Blocks;Photonic and Optical Materials;Dyestuff Intermediates
• Mol File: 100-01-6.mol
• Article Data: 828

Chemical Properties

• Melting Point: 147-151℃
• Boiling Point: 333.051°C at 760 mmHg
• Flash Point: 165°C
• Density: 1.334g/cm³
• Vapor Density: 4.77 (vs air)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: Store at R.T.
• Solubility: ethanol: soluble25mg/mL, slightly hazy, yellow to brownish-yellow
• PKA: 1(at 25℃)
• Water Solubility: 0.8 g/L (20℃)
• Stability: Stable. Incompatible with sodium hydroxide, strong oxidizing agents, strong reducing agents. May attack some plastics, rubber and coatings. May decompose explosively in the presence of initiators. Moisture sensitive. May be light and air-sensitive.
• Merck: 14,6584
• BRN: 508690
• CAS DataBase Reference: 4-Nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitroaniline(100-01-6)
• EPA Substance Registry System: 4-Nitroaniline(100-01-6)

Safety Data

• Hazard Codes: T:Toxic
• Statements: R23/24/25:; R33:; R52/53:
• Safety Statements: S28A:; S36/37:; S45:; S61:
• RIDADR: UN 1661 6.1/PG 2
• WGK Germany: 2
• RTECS: BY7000000
• F: 8
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 100-01-6(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 100-01-6 differently. You can refer to the following data:
1. Yellow fine crystals
2. p-Nitroaniline consists of yellow crystals with a pungent, faint ammonia-like odor.

Physical properties

Bright yellow crystalline powder or flakes with a faint, ammonia-like, slightly pungent odor. Combustible.

Uses

Different sources of media describe the Uses of 100-01-6 differently. You can refer to the following data:
1. Product of chromogenic reactions.
2. 4-Nitroaniline is used in the synthesis of photorefractive polymers, as novel chromophores in analytical study. As well, due to the absorption spectrum associated with 4-Nitroaniline, it is used to de termine catechol derivatives in syntheses.
3. Dyestuff intermediate.

Definition

ChEBI: A nitroaniline carrying a nitro group at position 4.

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 4114, 1994 DOI: 10.1021/jo00094a021Synthetic Communications, 20, p. 293, 1990 DOI: 10.1080/00397919008052297

General Description

Yellow solid with a mild odor. Sinks in water.

Air & Water Reactions

4-Nitroaniline may be sensitive to prolonged exposure to air and light. Insoluble in water. 4-Nitroaniline is sensitive to moisture.

Reactivity Profile

P-NITROANILINE may react vigorously with sulfuric acid above 392° F. 4-Nitroaniline may also react with sodium hydroxide at 266° F. Under pressure, 4-Nitroaniline may produce an explosive compound. 4-Nitroaniline is incompatible with strong oxidizers and strong reducing agents. 4-Nitroaniline is capable of explosive decomposition with strong initiators. 4-Nitroaniline will attack some forms of plastics, rubber and coatings.

Hazard

Explosion risk. Toxic when absorbed by skin. Methemoglobinemia, liver damage and eye irritant. Questionable carcinogen.

Health Hazard

Inhalation or ingestion causes headache, drowsiness, shortness of breath, nausea, methemoglobinemia, and unconsciousness; fingernails, lips, and ears become bluish; prolonged and excessive exposures may also cause liver damage. Contact with eyes causes irritation and possible corneal damage. Contact with skin causes irritation; continued exposure may cause same symptoms as inhalation or ingestion.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Moderately toxic by intramuscular route. Mutation data reported. Acute symptoms of exposure are headache, nausea, vomiting, weakness and stupor, cyanosis and methemoglobinemia. Chronic exposure can cause liver damage. Experimental reproductive effects. Combustible when exposed to heat or flame. See NITRATES for explosion and disaster hazards. To fight fire, use water spray or mist, foam, dry chemical, CO2. Vigorous reaction with sulfuric acid above 200°C. Reaction with sodium hydroxide at 13O°C under pressure may produce the explosive sodium-4-nitrophenoxide. When heated to decomposition it emits toxic fumes of NOx. See also m- NITROANILINE, o-NITROANILINE, NITRO COMPOUNDS OF AROMATIC HYDROCARBONS, and ANILINE DYES.

Potential Exposure

p-Nitroaniline is used as an intermediate in the manufacture of dyes; antioxidants, pharmaceuticals, antiozonants, colors, pigments and pesticides.

Carcinogenicity

p-Nitroaniline has been tested in several strains of S. typhimurium. It was mutagenic in strain TA98 but not in strains TA97, TA100, TA1535, and TA1537, with and without S9. It caused gene mutation in mouse lymphoma cells and chromosomal aberrations in CHO cells in the presence of S9.

Environmental fate

Biological. A Pseudomonas sp. strain P6, isolated from a Matapeake silt loam, was grown using a yeast extract. After 8 d, 4-nitroaniline degraded completely to carbon dioxide (Zeyer and Kearney, 1983). In activated sludge inoculum, following a 20-d adaptation period, no degradation was observed (Pitter, 1976). Chemical/Physical: Spacek et al. (1995) investigated the photodegradation of 4-nitroaniline using titanium dioxide-UV light and Fenton’s reagent (hydrogen peroxide:substance – 10:1; Fe2+ 2.5 x 10-4 mol/L). Both experiments were conducted at 25 °C. The decomposition rate of 4-nitroaniline was very high by the photo-Fenton reaction in comparison to titanium dioxide-UV light (λ = 365 nm). Decomposition products identified in both reactions were nitrobenzene, pbenzoquinone, hydroquinone, oxalic acid, and resorcinol. Oxalic acid, hydroquinone, and pbenzoquinone were identified as intermediate products using HPLC. At influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacities were 250, 140, 74, and 40 mg/g, respectively (Dobbs and Cohen, 1980).

Shipping

UN1661 Nitroanilines (m-, o-, p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

It also crystallises from acetone. It is freed from o-and m-isomers by zone melting and sublimation. [Beilstein 12 IV 1613.]

Incompatibilities

A combustible liquid. A strong oxidizer. Incompatible with strong acids; sulfur, combustibles, organics, and other easily oxidizable materials. Will accelerate the burning of combustible materials. If large quantities are involved in a fire or the combustible material is finely divided, an explosion may result. Prolonged exposure to fire or heat may result in an explosion.

Waste Disposal

Incineration (982℃, 2.0 seconds minimum) with scrubbing for nitrogen oxides abatement. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

Synthetic route

para-dinitrobenzene (100-25-4) → 4-nitro-aniline (100-01-6)

Conditions	Yield
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-nitro-aniline (100-01-6)

Conditions	Yield
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) → di(p-nitrophenyl) disulfide (100-32-3) + Toluene-3-thiosulfonic acid; compound with ammonia (77853-09-9) + 4-nitro-aniline (100-01-6)

Conditions	Yield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;	A 43% B 100% C 40%

1-methoxy-4-((4-nitrophenyl)sulfonyl)benzene (22865-57-2) → di(p-nitrophenyl) disulfide (100-32-3) + 4-Methoxy-benzenethiosulfonic acid; compound with ammonia (77853-03-3) + 4-nitro-aniline (100-01-6)

Conditions	Yield
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;

p-nitrophenyl isocyanide (1984-23-2) → 4-nitro-aniline (100-01-6)

Conditions	Yield
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-nitro-aniline (100-01-6)

Conditions	Yield
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) → 4-nitro-aniline (100-01-6)

Conditions	Yield
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) → 4-nitro-aniline (100-01-6)

Conditions	Yield
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) → 4-nitro-aniline (100-01-6)

Conditions	Yield
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) + 3,5-dinitro-1-(4-nitrophenyl)-4-pyridone (74197-40-3) → 4-nitro-aniline (100-01-6) + (S)-2-(3,5-Dinitro-4-oxo-4H-pyridin-1-yl)-4-methylsulfanyl-butyric acid (92782-41-7)

Conditions	Yield
In pyridine; water for 3h; Ambient temperature;	A n/a B 98%

α-naphthol (90-15-3) + 4'-nitrobenzenesulfenanilide (64168-52-1) → 2-phenylthio-1-naphthol (68143-73-7) + 4-(phenylthio)naphthalen-1-ol (19133-53-0) + 4-nitro-aniline (100-01-6) + 2,4-bis(phenylthio)naphthalen-1-ol (103929-98-2)

Conditions	Yield
With trifluoroacetic acid In benzene for 0.166667h; Ambient temperature; Further byproducts given;	A 42% B 33% C 98% D 10%

α-naphthol (90-15-3) + 4'-nitrobenzenesulfenanilide (64168-52-1) → 2-phenylthio-1-naphthol (68143-73-7) + 4-(phenylthio)naphthalen-1-ol (19133-53-0) + 4-nitro-aniline (100-01-6) + diphenyldisulfane (882-33-7)

Conditions	Yield
With trifluoroacetic acid In benzene for 0.166667h; Ambient temperature; Further byproducts given;	A 42% B 33% C 98% D 14%

α-naphthol (90-15-3) + 4'-nitrobenzenesulfenanilide (64168-52-1) → 2-phenylthio-1-naphthol (68143-73-7) + 4-(phenylthio)naphthalen-1-ol (19133-53-0) + 4-nitro-aniline (100-01-6) + 2,4-bis(phenylthio)naphthalen-1-ol (103929-98-2) + diphenyldisulfane (882-33-7)

Conditions	Yield
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%

4'-nitrobenzenesulfenanilide (64168-52-1) → S-Phenyl benzenethiosulfonate (1212-08-4) + 4-nitro-aniline (100-01-6) + diphenyldisulfane (882-33-7)

Conditions	Yield
With trifluoroacetic acid In benzene at 25℃; Product distribution; Mechanism; further sulfenanilide;	A 32% B 98% C 56%

trifluoroacetic acid (76-05-1) + S,S-di-n-butyl-N-(4-nitrophenyl)imino-λ4-sulfane → butyl sulfoxide (2168-93-6) + 2,2,2-trifluoro-N-(4-nitrophenyl)acetamide (404-27-3) + 4-nitro-aniline (100-01-6)

Conditions	Yield
at 72℃; for 72h; Elimination; acylation; retro-Pummerer reaction;	A 79% B 98% C 2%

N-(4-Nitrophenyl)acetamide (104-04-1) → 4-nitro-aniline (100-01-6)

Conditions	Yield
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) → 4-nitro-aniline (100-01-6)

Conditions	Yield
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) + C11H14N2O4 (88867-70-3) → 4-nitrosonitrobenzene (4485-08-9) + 4-nitro-aniline (100-01-6)

Conditions	Yield
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;

C11H14N2O4 (88867-70-3) → 4-nitro-aniline (100-01-6)

Conditions	Yield
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) + methylamine (74-89-5) → 1,3-dimethyl-5-nitrouracil (41613-26-7) + 4-nitro-aniline (100-01-6)

Conditions	Yield
In methanol for 0.5h; Ambient temperature;	A 95% B n/a

4-nitrophenyl azide (1516-60-5) + diethyl malonate (105-53-3) → 1,3-diethyl 2-diazopropanedioate (5256-74-6) + 4-nitro-aniline (100-01-6)

Conditions	Yield
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 %

ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate (78596-42-6) → 4-nitro-aniline (100-01-6)

Conditions	Yield
With ethylenediamine In ethanol at 20℃; for 2.3h;	95%

pyridine (110-86-1) + 3,5-dinitro-1-(4-nitrophenyl)-4-pyridone (74197-40-3) → 4-nitro-aniline (100-01-6) + 1-Hydroxy-3,5-dinitro-1H-pyridin-4-one; compound with pyridine (139055-63-3)

Conditions	Yield
With hydroxylamine hydrochloride at 20℃; for 2h;	A 94% B 83%

C14H13NO5S (77863-74-2) → di(p-nitrophenyl) disulfide (100-32-3) + 3-Ethoxy-benzenethiosulfonic acid; compound with ammonia (77853-06-6) + 4-nitro-aniline (100-01-6)

Conditions	Yield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;	A 47% B 94% C 40%

C11H14N2O4 (88867-70-3) + N-(4-chlorophenyl)hydroxylamine (823-86-9) → 1-chloro-4-nitroso-benzene (932-98-9) + 4-nitro-aniline (100-01-6)

Conditions	Yield
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;

nitrobenzene (98-95-3) → 4-nitrosoaniline (659-49-4) + 4-nitro-aniline (100-01-6)

Conditions	Yield
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) → 4-nitro-aniline (100-01-6)

Conditions	Yield
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) + 3,5-dinitro-1-(4-nitrophenyl)-4-pyridone (74197-40-3) → 4-nitro-aniline (100-01-6) + 4-aci-Nitro-4H-isoxazol-5-one; compound with pyridine

Conditions	Yield
With hydroxylamine hydrochloride at 20℃; for 2h;	A 93% B 88%

para-dinitrobenzene (100-25-4) → 4-Nitro-N-phenylhydroxylamine (16169-16-7) + 4-nitro-aniline (100-01-6)

Conditions	Yield
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) → di(p-nitrophenyl) disulfide (100-32-3) + 3,5-Dichloro-benzenethiosulfonic acid; compound with ammonia (77853-10-2) + 4-nitro-aniline (100-01-6)

Conditions	Yield
With sulfur; ammonia at 100℃; for 2h; titanium autoclave;	A 42% B 93% C 40%

4-nitrobenzaldehdye (555-16-8) + 4-nitro-aniline (100-01-6) → N-(4-nitrobenzylidene)-4-nitroaniline (10480-05-4)

Conditions	Yield
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) + 4-nitro-aniline (100-01-6) → 4-nitro-N-(phenylmethylene)benzenamine (785-81-9, 1613-94-1, 40339-44-4)

Conditions	Yield
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) + butyryl chloride (141-75-3) → N-(4'-nitrophenyl)butyramide (54191-12-7)

Conditions	Yield
With NMM In dichloromethane	100%
With triethylamine In dichloromethane at 20℃;	71%
With sodium hydroxide; acetone

4-nitro-aniline (100-01-6) + p-toluenesulfonyl chloride (98-59-9) → N-(4-nitrophenyl)-4-methylbenzenesulfonamide (734-25-8)

Conditions	Yield
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) + 2-chloropropionyl chloride (625-36-5) → 3-chloro-N-(4-nitrophenyl)propanamide (19313-88-3)

Conditions	Yield
at 0 - 50℃; Neat (no solvent);	100%
at 20 - 50℃;	100%
at 50℃; for 16h;	97%

4-nitro-aniline (100-01-6) + diethyl 2-ethoxymethylenemalonate (87-13-8) → ethyl α-ethoxycarbonyl-β-(4-nitroanilino)acrylate (78596-42-6)

Conditions	Yield
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) → p-nitrobenzene iodide (636-98-6)

Conditions	Yield
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-nitrophenyl azide (1516-60-5)

Conditions	Yield
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-nitrobenzenediazonium chloride (100-05-0)

Conditions	Yield
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-chlorobenzonitrile (100-00-5)

Conditions	Yield
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) → 1,4-phenylenediamine (106-50-3)

Conditions	Yield
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) + β-naphthol (135-19-3) → para red (6410-10-2)

Conditions	Yield
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) + phenol (108-95-2) → 4-(4'-hydroxyphenylazo)nitrobenzene (1435-60-5, 81944-71-0)

Conditions	Yield
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) + 4-nitro-aniline (100-01-6) → ethyl 5-methyl-3-(4-nitrophenylazo)-2-phenylpyrrole-4-carboxylate

Conditions	Yield
With hydrogenchloride; sodium acetate; sodium nitrite In acetic acid at 0℃; for 1h;	100%

4-methoxy-benzaldehyde (123-11-5) + 4-nitro-aniline (100-01-6) → N-(4-methoxybenzylidene)-4-nitroaniline (15450-66-5)

Conditions	Yield
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) + 4-nitro-aniline (100-01-6) → N-p-nitrophenyl-6,7-dideoxy-L-galacto-hept-6-enosylamine (128357-86-8)

Conditions	Yield
In methanol; acetic acid at 110℃; for 0.166667h;	100%

4-nitro-aniline (100-01-6) + phenylacetyl chloride (103-80-0) → N-(4-nitrophenyl)-2-phenylacetamide (13140-77-7)

Conditions	Yield
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) + Acetic formic anhydride (2258-42-6) → p-nitroformanilide (16135-31-2)

Conditions	Yield
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) → p-nitrobenzene diazonium nitrate

Conditions	Yield
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) + 4-nitro-aniline (100-01-6) → [Chloro-(4-nitro-phenylamino)-methylene]-dimethyl-ammonium; chloride

Conditions	Yield
at -20℃; for 1h; ball mill;	100%

4-chlorobenzaldehyde (104-88-1) + 4-nitro-aniline (100-01-6) → (4-chlorobenzylidene)(4-nitrophenyl)amine (5340-14-7)

Conditions	Yield
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) + 4-methoxy-aniline (104-94-9) + 4-nitro-aniline (100-01-6) → (E)-N-(4-methoxybenzylidene)-4-nitroaniline (97221-15-3)

Conditions	Yield
In dichloromethane Condensation; Heating;	100%

acetophenone dimethyl acetal (4316-35-2) + 4-nitro-aniline (100-01-6) → (4-nitrophenyl)(1-phenylethylidene)amine

Conditions	Yield
In dichloromethane Condensation; Heating;	100%

4-nitro-aniline (100-01-6) + 2,2-dimethoxy-propane (77-76-9) → N-isopropylidene-4-nitro-aniline (22104-23-0)

Conditions	Yield
In dichloromethane Condensation; Heating;	100%

bis(trichloromethyl) carbonate (32315-10-9) + tert-butyl 4-aminobenzoate (18144-47-3) + 4-nitro-aniline (100-01-6) → 1-(4'-nitrophenyl)-3-(4''-tert-butylcarboxyphenyl)urea (301317-92-0)

Conditions	Yield
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%

4-nitro-aniline (100-01-6) + 4-chloro-5-methoxy-2-methyl-2H-pyridazin-3-one (14628-57-0) → 5-methoxy-2-methyl-4-(4-nitro-phenylamino)-2H-pyridazin-3-one

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

Upstream product

• 10001-55-5 3-propyl-1,2,3-benzotriazin-4(3H)-one 
• 10001-54-4 3-isopropyl-1,2,3-benzotriazin-4(3H)-one 
• 1000152-84-0 2,6-DibroMo-4-(trifluoroMethyl)pyridine 
• 1000152-83-9 5-Nitro-4-trifluoromethyl-pyridin-2-ylamine 
• 10001-52-2 5-ethyl-5-(5H-purin-6-ylsulfanyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 100015-12-1 (E)-2-Hydroxymethyl-2-butenoic acid (E)-2-[[[(3aR)-2,3,3aβ,4,5,6,6aβ,7,9aβ,9bα-decahydro-7α-hydroxy-9-methyl-3,6-bismethylene-2-oxoazuleno[4,5-b]furan-4α-yl]oxy]carbonyl]-2-butenyl ester 
• 100014-94-6 (2S,4R,9beta,16alpha,23E)-2,16,20-trihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-5,23-dien-25-yl acetate - (4R,9beta,16alpha,23E)-2,16,20-trihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl a 
• 10001-46-4 1,3-dimethyl-5,8-dihydropyrido[2,3-d]pyrimidine-2,4,7(1H,3H,6H)-trione 
• 10001-43-1 Pimefylline 
• 10001-35-1 6,7-DiMethoxy-1,4-phthalazinediol 
• 100013-07-8 LITHIUM B-ISOPINOCAMPHEYL-9-BORABICYCLO[3.3.1]NONYL HYDRIDE 
• 100012-45-1 6-CHLORO-2-[2-(3-[(6-CHLORO-1-ETHYLBENZ[C,D,]INDOLE-2[1H]-YLIDENE)ETHYLIDENE]-2-PHENYL-1-CYCLOPENTEN-1-YL)ETHENYL]-1-ETHYLBENZ[C,D]INDOLIUM TETRAFLUOROBORATE 
• 100011-37-8 (η-cumene)-(η-cyclopentadienyl)iron(II) hexafluoroantimonate 
• 10001-13-5 Pexantel 

Downstream Products

• 1000160-74-6 2-(benzo[b]thiophen-7-yl)-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane 
• 1000160-75-7 Benzo[b]thiophen-4-ylboronic acid pinacol ester 
• 1000162-78-6 Benzoic acid, 2-fluoro-5-iodo-4-Methoxy- 
• 1000-16-4 diethyl [(dibutylamino)methyl]phosphonate 
• 1000164-43-1 FMOC-SER(TBU)-SER(PSIME,MEPRO)-OH 
• 100016-62-4 CALCITONIN, CHICKEN 
• 1000166-82-4 (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone 
• 100016-73-7 caustinerf 
• 1000169-10-7 3-(2-(3-PYRIDYL)VINYL)HYDROQUINOXALIN-2-ONE 
• 100016-94-2 SESAMOLINOL 
• 1000171-05-0 2′-Dicyclohexylphosphino-2,4,6-trimethoxybiphenyl 
• 100017-18-3 (2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE 
• 1000181-36-1 Spiro[4H-1-benzazepine-4,1'-[2]cyclopentene]-3'-carboxylic acid, 1,2,3,5-tetrahydro-, ethyl ester 
• 10001-82-8 AMpicillin EP IMpurity I 

Recommend Products

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• 100-25-4  para-dinitrobenzene 
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