89-63-4

Basic information

• Product Name: 4-Chloro-2-nitroaniline
• Synonyms: fastred2ncsalt;fastred3glspecialbase;fastred3glspecialsalt;FastRed3GLSpecid;fastredbase;fastredbase3glspecial;fastredbase3jl;fastredsalt3jl
• CAS NO: 89-63-4
• Molecular Formula: C₆H₅ClN₂O₂
• Molecular Weight: 172.57
• EINECS: 201-925-4
• Product Categories: Intermediates of Dyes and Pigments;Anilines, Aromatic Amines and Nitro Compounds;Organics;Amines;Aromatics;Mutagenesis Research Chemicals;Dyestuff Intermediates
• Mol File: 89-63-4.mol
• Article Data: 42

Chemical Properties

• Melting Point: 117-119 °C(lit.)
• Boiling Point: 200°C (rough estimate)
• Flash Point: 191 °C
• Appearance: Orange/Crystalline Powder or Chunks
• Density: 1.37
• Vapor Pressure: 0.000667mmHg at 25°C
• Refractive Index: 1.6460 (estimate)
• Storage Temp.: room temp
• Solubility: 0.5g/l (anhydrous substance)
• PKA: pK1: 1.10(+1) (25°C)
• Water Solubility: INSOLUBLE
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 512436
• CAS DataBase Reference: 4-Chloro-2-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2-nitroaniline(89-63-4)
• EPA Substance Registry System: 4-Chloro-2-nitroaniline(89-63-4)

Safety Data

• Hazard Codes: T+,N,T
• Statements: 26/27/28-33-51/53
• Safety Statements: 28-36/37-45-61-28A
• RIDADR: UN 2237 6.1/PG 3
• WGK Germany: 2
• RTECS: BX1575000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 89-63-4(Hazardous Substances Data)

Usage

Chemical Properties

bright orange powder

Uses

Different sources of media describe the Uses of 89-63-4 differently. You can refer to the following data:
1. A nitro-aromatic amine with mutagenicity and carcinogenicity
2. 4-Chloro-2-nitroaniline is used almost exclusively as an intermediate in the synthesis of pigments. The greatest potential for human exposure to 4-chloro-2- nitroaniline is in production and use of pigments made from the compound.
3. 4-Chloro-2-nitroaniline is used as pharmaceutical intermediate.

Preparation

4-Chloro-2-nitrobenzenamine of chlorine.

General Description

Bright orange powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-Chloro-2-nitroaniline forms explosive products on reaction with nitric acid. Can react with oxidizing agents.

Hazard

Toxic by ingestion and inhalation.

Fire Hazard

4-Chloro-2-nitroaniline is probably combustible.

Purification Methods

Crystallise the aniline from hot H2O (m 115.8-116o), EtOH, EtOH/H2O or *C6H6, and dry it for 10hours at 60o in vacuo. It has m 115.5-116o after sublimation. [Beilstein 12 H 729, 12 I 355, 12 II 396, 12 III 1649, 12 IV 1669.]

InChI:InChI=1/C6H5ClN2O2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H,8H2

Synthetic route

2-nitro-aniline (88-74-4) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.0833333h; Green chemistry;	99.2%
With copper dichloride; 1-hexyl-3-methylimidazol-1-ium chloride at 40℃; for 16h; regioselective reaction;	85%
With N-chloro-succinimide In acetonitrile for 10h; Heating;	57%
Multi-step reaction with 2 steps 1: diethyl ether; hypochlorous acid / 20 °C 2: hydrochloric acid; diethyl ether / -20 °C View Scheme

3,4-dinitro-chlorobenzene (610-40-2) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With sodium tetrahydroborate In ethanol; water at 20℃; for 4h; Green chemistry;	90%

4-chloro-aniline (106-47-8) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 3h;	92%
Multi-step reaction with 3 steps 1: acetic acid / 0.25 h / Heating 2: 60percent nitric acid, conc. sulfuric acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min 3: conc. sulfuric acid / 0.25 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane 2: nitric acid; acetic anhydride / dichloromethane 3: hydrogenchloride / water / Reflux View Scheme

N-(4-chloro-2-nitrophenyl) pyrimidin-2-amine → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
Stage #1: N-(4-chloro-2-nitrophenyl) pyrimidin-2-amine With triethylsilane; trifluoroacetic acid at 50℃; Inert atmosphere; Stage #2: With acetic acid; hydrazine In methanol at 20℃; Inert atmosphere; regioselective reaction;	80%

3-chloro-aniline (108-42-9) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With nitric acid In sulfuric acid; acetic acid at 20 - 25℃; for 10.5h; Temperature;

3-Chloronitrobenzene (121-73-3) → 2-chloro-6-nitroaniline (769-11-9) + 4-Chloro-2-nitroaniline (89-63-4) + 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
With 2,4,6-trichlorosulfenamide; potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 0.333333h;	A 26% B 7% C 38%
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide for 1h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide In dimethyl sulfoxide Ambient temperature; Yield given. Yields of byproduct given;
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride In N,N-dimethyl-formamide at 20℃; Substitution; Amination; Title compound not separated from byproducts;

N-(2-nitro-4-chlorophenyl)benzamide (52010-24-9) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With potassium hydroxide In methanol at 20℃; for 12h;	99%

N-(4-chloro-2-nitrophenyl)-acetamide (881-51-6) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With sulfuric acid
With hydrogenchloride
With sodium methylate

o-azidonitrobenzene (1516-58-1) → 2-chloro-6-nitroaniline (769-11-9) + 2-nitro-aniline (88-74-4) + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With boron trichloride In benzene Ambient temperature;	A 17% B 3% C 64%
With boron trichloride In benzene at 50℃; for 6h;	A 3% B 3% C 64%
With boron trichloride In benzene at 50℃; for 6h;	A 17% B 3% C 64%

N-(4-chlorophenyl)acetamide (539-03-7) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With nitric acid Kochen des Reaktionsproduktes mit Natronlauge;
With nitric acid at -10℃; durch Erwaermen des Reaktionsprodukts mit etwas konz. Schwefelsaeure auf 100grad;
Multi-step reaction with 2 steps 1: 60percent nitric acid, conc. sulfuric acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min 2: conc. sulfuric acid / 0.25 h / 100 °C View Scheme

2-nitro-aniline (88-74-4) → 2-chloro-6-nitroaniline (769-11-9) + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With trichloroisocyanuric acid; brilliant green carbocation In acetonitrile at 20℃; for 1.5h; Irradiation; Overall yield = 94 %; Overall yield = 81.1 mg; regioselective reaction;

2-(4-chloro-2-nitrophenylamino)ethanol (59320-13-7) + methanesulfonyl chloride (124-63-0) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
In pyridine; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate

2,5-dichloronitrobenzene (89-61-2) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With ammonia; water at 175℃; im Eisen-Autoklaven;
With ethanol; ammonia at 165℃;
With ethanol; ammonia at 200 - 220℃;
With NH2

(4-chloro-phenyl)-pyrimidin-2-yl-amine → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: palladium diacetate; silver(I) nitrite; dipotassium peroxodisulfate; acetic acid / 1,2-dichloro-ethane / 80 °C / Inert atmosphere 2.1: trifluoroacetic acid; triethylsilane / 50 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere View Scheme

4-Chloro-1,2-phenylenediamine (95-83-0) → 5-chloro-2-nitroaniline (1635-61-6) + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h; Overall yield = 93 %;	A 49 %Chromat. B 51 %Chromat.

1-azido-4-methyl-2-nitrobenzene (89284-67-3) → 4-Chloro-2-nitroaniline (89-63-4) + 6-chlorobenzo[c][1,2,5]oxadiazole 1-oxide (39060-31-6) + 1-(4-Chloro-2-nitro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (210989-45-0)

Conditions	Yield
With diethyl acetylmalonate; sodium ethanolate In ethanol for 5h; Ambient temperature;	A 35% B 27% C 25%

N-(4-chlorophenyl)acetamide (539-03-7) → N-(4-chloro-2-nitrophenyl)-acetamide (881-51-6) + N-(4-chloro-3-nitrophenyl)acetamide (5540-60-3) + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With sodium nitrate; sulfuric acid for 3h; Ambient temperature;	A 62% B 9% C 21%

1-azido-4-methyl-2-nitrobenzene (89284-67-3) + diethyl 1,3-acetonedicarboxylate (105-50-0) → 4-Chloro-2-nitroaniline (89-63-4) + 6-chlorobenzo[c][1,2,5]oxadiazole 1-oxide (39060-31-6) + 1-(4-Chloro-2-nitro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (210989-45-0)

Conditions	Yield
With sodium ethanolate In ethanol for 5h; Ambient temperature;	A 35% B 27% C 25%

N,N-dichloro-2-nitroaniline (59483-70-4) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With hydrogenchloride; diethyl ether at -20℃;

2,5-dichloronitrobenzene (89-61-2) + ammonium carbonate → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With basic copper carbonate powder; ethylene glycol at 130 - 140℃;

N-(4-chlorophenyl)benzamide (2866-82-2) → 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid; copper(II) nitrate hydrate; oxygen / acetonitrile; water / 12 h / 100 °C / 760.05 Torr 2: potassium hydroxide / methanol / 12 h / 20 °C View Scheme

4-chloro-aniline (106-47-8) → 4-Chloro-3-nitroaniline (635-22-3) + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With sulfuric acid; nitric acid at -20℃;

3,4-dinitro-chlorobenzene (610-40-2) → 5-chloro-2-nitroaniline (1635-61-6) + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With titanium(III) chloride In methanol; water Title compound not separated from byproducts;	A 19.10 % Chromat. B 15.90 % Chromat.

tert-butylhypochlorite (507-40-4) + 2-nitro-aniline (88-74-4) → 2-chloro-6-nitroaniline (769-11-9) + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
With tert-butyl alcohol; benzene
With acetic acid; benzene
With benzene
With tert-butyl alcohol
With acetic acid

dibutyl ether (142-96-1) + 4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid → 1-Butoxy-butane; compound with trifluoro-methanesulfonic acid + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔH, ΔS;

1,1,3,3-Tetramethyldisiloxane (3277-26-7) + 4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid → Trifluoro-methanesulfonic acid; compound with 1,1,3,3-tetramethyl-disiloxane + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔS, ΔH;

Hexamethyldisiloxane (107-46-0) + 4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid → 1,1,1,3,3,3-Hexamethyl-disiloxane; compound with trifluoro-methanesulfonic acid + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔH, ΔS;

Octamethyltrisiloxane (107-51-7) + 4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid → C8H24O2Si3*CHF3O3S + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔH, ΔS;

Hexamethylcyclotrisiloxane (541-05-9) + 4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid → 2,2,4,4,6,6-Hexamethyl-[1,3,5,2,4,6]trioxatrisilinane; compound with trifluoro-methanesulfonic acid + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔH, ΔS;

methyltrimethicone (17928-28-8) + 4-Chloro-2-nitro-phenylamine; compound with trifluoro-methanesulfonic acid → C10H30O3Si4*CHF3O3S + 4-Chloro-2-nitroaniline (89-63-4)

Conditions	Yield
In benzene at 26.9℃; Equilibrium constant; Thermodynamic data; ΔG, ΔH, ΔG;

4-Chloro-2-nitroaniline (89-63-4) + dimethyl sulfate (77-78-1) → 4-chloro-N-methyl-2-nitroaniline (15950-17-1)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; toluene at 20℃; Methylation;	100%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water; toluene at 20℃;	94%

4-Chloro-2-nitroaniline (89-63-4) → 2-bromo-4-chloro-6-nitrobenzenamine (827-25-8)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile Reflux;	100%
With bromine; acetic acid at 0 - 20℃; for 1h;	100%
With bromine; acetic acid at 0 - 20℃; for 1h; Cooling with ice;	100%

(3R)-4-[2-chloro-6-(1-methanesulfonylcyclopropyl)pyrimidin-4-yl]-3-methylmorpholine (1233339-68-8) + 4-Chloro-2-nitroaniline (89-63-4) → (R)-N-(4-chloro-2-nitrophenyl)-4-(3-methylmorpholino)-6-(1-(methylsulfonyl)cyclopropyl)pyrimidin-2-amine

Conditions	Yield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃; for 1h; Buchwald-Hartwig Coupling; Microwave irradiation; Sealed tube; Inert atmosphere;	100%

thiophene boronic acid (6165-68-0) + 4-Chloro-2-nitroaniline (89-63-4) → 2-nitro-4-thiophen-2-yl-phenylamine (405170-93-6)

Conditions	Yield
With potassium phosphate; (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate In 1,4-dioxane; water for 20h; Sealed tube; Schlenk technique; Inert atmosphere;	100%

4-Chloro-2-nitroaniline (89-63-4) → 4-Chloro-1,2-phenylenediamine (95-83-0)

Conditions	Yield
With samarium; 1,1’-di-n-octyl-4,4’-bipyridinium dibromide In methanol at 20℃; for 5.5h;	99%
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; for 0.133333h; Microwave irradiation; chemoselective reaction;	98%
With palladium/alumina; hydrogen In ethanol at 125℃; for 8h; Flow reactor;	96%

trimethylsilyl acetate (2754-27-0) + 4-Chloro-2-nitroaniline (89-63-4) → N-(4-chloro-2-nitrophenyl)-acetamide (881-51-6)

Conditions	Yield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	99%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	99%

trimethylsilyl isobutyrate (16883-61-7) + 4-Chloro-2-nitroaniline (89-63-4) → 4'-chloro-2-methyl-2'-nitropropananilide (86569-53-1)

Conditions	Yield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	99%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	99%

trimethylsilyl 2,2-dimethylpropionate (37170-49-3) + 4-Chloro-2-nitroaniline (89-63-4) → 4'-chloro-2,2-dimethyl-2'-nitropropananilide

Conditions	Yield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	99%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	99%

3-methylbutyric acid trimethylsilyl ester (55557-13-6) + 4-Chloro-2-nitroaniline (89-63-4) → 4'-chloro-3-methyl-2'-nitrobutananilide

Conditions	Yield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	99%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	99%

4-Chloro-2-nitroaniline (89-63-4) + β-naphthol (135-19-3) → 1-(4'-chloro-2'-nitrophenylazo)-2-naphthol (6410-13-5)

Conditions	Yield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Stage #2: β-naphthol In water at 60℃; for 1h;	99%
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Green chemistry; Stage #2: β-naphthol In water at 60℃; for 1h; Green chemistry;	99%
With hydrogenchloride; sodium nitrite 1.) -10 deg C - 0 deg C, 5 min, 2.) EtOH, H2O; Yield given. Multistep reaction;
With hydrogenchloride; Amberlite-IR 120 (Na(1+) form); sodium nitrite 1.) 0-5 deg C, 2.) water, ethanol, RT, 30 min; Yield given. Multistep reaction;

2,5-dimethyl-2,3-dihydrofuran-3-one (14400-67-0) + 4-Chloro-2-nitroaniline (89-63-4) → 2,5-dimethyl-2-(4-chloro-2-nitrophenylazo)-3-oxo-2,3-dihydrofuran

Conditions	Yield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite at 20℃; for 1h; Stage #2: 2,5-dimethyl-2,3-dihydrofuran-3-one In water at 20℃; for 1h;	99%

di-tert-butyl dicarbonate (24424-99-5) + 4-Chloro-2-nitroaniline (89-63-4) → tert-butyl N-[(tert-butoxy)carbonyl]-N-(4-chloro-2-nitrophenyl)carbamate (1040363-35-6)

Conditions	Yield
dmap In tetrahydrofuran at 90℃; for 1h;	99%
With dmap In tetrahydrofuran at 25 - 90℃; for 6h;	58%

4-Chloro-2-nitroaniline (89-63-4) + isobutyraldehyde (78-84-2) → 4-chloro-2-nitro-N-(2-methyl-1-propen-1-yl)benzenamine (424799-62-2)

Conditions	Yield
With 4 A molecular sieve In benzene at 20℃; for 26h;	99%
Molecular sieve;
With magnesium sulfate In dichloromethane Schlenk technique; Inert atmosphere; Reflux; Sealed tube;

2'-methoxyacetoacetanilide (92-15-9) + 4-Chloro-2-nitroaniline (89-63-4) → pigment yellow 73 (13515-40-7)

Conditions	Yield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Stage #2: 2'-methoxyacetoacetanilide In water at 60℃; for 1h;	99%

5-acetoacetylamino-2-benzimidazolone + 4-Chloro-2-nitroaniline (89-63-4) → pigment orange 36

Conditions	Yield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.416667h; Stage #2: 5-acetoacetylamino-2-benzimidazolone In water at 60℃; for 2h; Time;	99%

N-phenylacetoacetamide (102-01-2) + 4-Chloro-2-nitroaniline (89-63-4) → pigment yellow 6 (4106-76-7)

Conditions	Yield
Stage #1: 4-Chloro-2-nitroaniline With hydrogenchloride; sodium nitrite In water for 0.666667h; Stage #2: N-phenylacetoacetamide In water at 20℃; for 0.166667h;	99%

trimethylsilyl 2-methylbenzoate (55557-15-8) + 4-Chloro-2-nitroaniline (89-63-4) → 4'-chloro-2-methyl-2'-nitrobenzanilide

Conditions	Yield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	98%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	98%

4-Chloro-2-nitroaniline (89-63-4) + ethyl chlorocarbonylacetate (36239-09-5) → ethyl 3-((4-chloro-2-nitrophenyl)amino)-3-oxopropanoate (143948-68-9)

Conditions	Yield
In dichloromethane at 20℃;	98%
In toluene for 24h; Heating;	63%

1,2-dibromo-1,2-diphenylethane (13440-24-9) + 4-Chloro-2-nitroaniline (89-63-4) → 2,3-diphenyl-6-chloroquinoxaline (36305-60-9)

Conditions	Yield
With N-hexylpyridine hexafluorophosphate; cisplatine; 4,7-Dimethyl-1,10-phenanthroline; diisopropanolamine In dimethyl sulfoxide at 80℃; for 12h; Reagent/catalyst; Inert atmosphere;	97.3%

4-Chloro-2-nitroaniline (89-63-4) + chloroacetyl chloride (79-04-9) → N-(4-chloro-2-nitrophenyl)-2-chloroacetamide (40930-49-2)

Conditions	Yield
In N,N-dimethyl-formamide Cooling with ice;	97%

trimethylsilyl ester of hydrocinnamic acid (21273-15-4) + 4-Chloro-2-nitroaniline (89-63-4) → 4'-chloro-2'-nitro-3-phenylpropananilide

Conditions	Yield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	97%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	97%

4-Chloro-2-nitroaniline (89-63-4) + 2,6-difluorobenzoylchloride (18063-02-0) → N,N-bis-(2,6-difluorobenzoyl)-4-chloro-6-nitroaniline (212503-94-1)

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃;	97%

formic acid (64-18-6) + 4-Chloro-2-nitroaniline (89-63-4) → N-(4-Chloro-2-nitro-phenyl)-formamide

Conditions	Yield
With Hexamethyldisiloxane; MS-5Angstroem; 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	96%

4-Chloro-2-nitroaniline (89-63-4) → 3-Chloronitrobenzene (121-73-3)

Conditions	Yield
With tetrahydrofuran; tert.-butylnitrite; dimethyl sulfoxide at 30℃; for 1h; Green chemistry;	96%

benzyl bromide (100-39-0) + 4-Chloro-2-nitroaniline (89-63-4) → N-benzyl-4-chloro-2-nitrobenzenamine (10066-18-9)

Conditions	Yield
In water at 100℃; for 1.5h;	95%
In water at 100℃;	85%
In water at 100℃; for 2h; Green chemistry;	85%

nitratocarbonylbis(triphenylphosphine)rhodium (22654-78-0, 99664-53-6) + 4-Chloro-2-nitroaniline (89-63-4) → RhCO(P(C6H5)3)2HNC6H3ClNO2

Conditions	Yield
With KOH In methanol; acetone to an acetone soln. of Rh complex were added equimolar quantity of nitroaniline (in acetone) and KOH in MeOH; solvents were evpd. in vac., red residue extd. with benzene and filtered from KNO3; solvent removed in vac., crystals pptd. with hexane, filtered, washed with hexane and dried in air; elem. anal.;	95%

4-hydroxy-benzaldehyde (123-08-0) + 4-Chloro-2-nitroaniline (89-63-4) + phosphonic acid diethyl ester (762-04-9) → diethyl (4-chloro-2-nitrophenylamino)(4-hydroxyphenyl)methylphosphonate (1296865-37-6)

Conditions	Yield
With ethylammonium nitrate at 20℃; for 4h;	95%

4-Chloro-2-nitroaniline (89-63-4) + 2.3-butanediol (513-85-9) → 6-chloro-2,3-dimethyl-quinoxaline (17911-93-2)

Conditions	Yield
With cesiumhydroxide monohydrate; C17H14Br2CoN4 In toluene at 150℃; for 24h; Sealed tube; Inert atmosphere;	95%
With sodium hydroxide In toluene at 120℃; for 3h; Inert atmosphere; Sealed tube; Green chemistry;	77%
With dodecacarbonyl-triangulo-triruthenium; cesiumhydroxide monohydrate; 1,3-bis-(diphenylphosphino)propane In tert-Amyl alcohol at 150℃; for 8h; Schlenk technique; Inert atmosphere;	68%
With 1,10-Phenanthroline; cesiumhydroxide monohydrate; nickel dibromide In toluene at 150℃; for 24h; Inert atmosphere; Sealed tube;	64%
With cobalt supported on N,P co-doped porous carbon In toluene at 140℃; for 12h; Sealed tube; Inert atmosphere;	81 %Chromat.

Upstream product

• 345-18-6 2-fluoro-5-chloronitrobenzene 
• 71331-67-4 4-chloroanilinium nitrate 
• 108-24-7 acetic anhydride 
• 88-74-4 2-nitro-aniline 
• 631-61-8 ammonium acetate 
• 89-61-2 2,5-dichloronitrobenzene 
• 556-67-2 octamethylcyclotetrasiloxane 
• 141-63-9 dodecamethylpentasiloxane 
• 3555-47-3 1,1,1,5,5,5-hexamethyl-3,3-bis(trimethylsiloxy)trisiloxane 
• 541-02-6 decamethylcyclopentasiloxane 
• 92884-98-5 Acetic acid (4-chloro-2-nitro-phenylcarbamoyl)-phenyl-methyl ester 
• 69732-97-4 4-chloro-N-nitro-aniline 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 

Downstream Products

• 85142-54-7 4-Chloro-2-nitrofumaranilic acid 
• 94210-21-6 2-(4-chloro-2-nitrophenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 10066-18-9 N-benzyl-4-chloro-2-nitrobenzenamine 
• 52010-24-9 N-(2-nitro-4-chlorophenyl)benzamide 
• 66367-04-2 N-4-chloro-2-nitrophenylglycine 
• 7153-86-8 (4-chloro-2-nitro-phenyl)-urea 
• 2955-16-0 bis(4-chloro-2-nitroanilino)methane 
• 680579-53-7 3-bromo-butyric acid-(4-chloro-2-nitro-anilide) 
• 18671-92-6 7-chloro-1-oxido-1,2,4-benzotriazin-1-ium-3-amine 
• 183543-61-5 3-Bromo-6-chloro-8-nitroquinoline 
• 104968-22-1 2-(4-chloro-2-nitro-anilino)-benzophenone 
• 17348-69-5 5-chlorobenzofurazan-1-oxide 
• 857468-11-2 N,N'-bis-(4-chloro-2-nitro-phenyl)-p-phenylenediamine 
• 40930-49-2 N-(4-chloro-2-nitrophenyl)-2-chloroacetamide 

Relevant articles and documents

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Fenbendazole production process and production device

The invention discloses a fenbendazole production process and a production device, the production process comprises a nitration reaction, a condensation reaction, a reduction reaction and a cyclization reaction, and finally the fenbendazole is obtained through centrifugation and drying. The production device comprises a plurality of reaction kettles, a distillation device and a distillation recovery device, the reaction kettles are respectively a nitration reaction kettle, a condensation reaction kettle, a cyclization reaction kettle and a reduction reaction kettle, and the nitration reactionkettle, the condensation reaction kettle, the cyclization reaction kettle, the distillation device and the reduction reaction kettle are sequentially communicated through feeding pipes. According to the process, the product purity can be improved; few types of chemical reagents are adopted, and methanol and methylbenzene are recycled so that reagent consumption is reduced, waste is avoided, and the process is economical and environmentally friendly; the process route is simple, the production period is shortened, and the production efficiency is improved; according to the production device, automatic feeding is achieved through the feeding mechanism, the automation degree is high, manual operation is reduced, and efficiency is improved.

Amplification of Trichloroisocyanuric Acid (TCCA) Reactivity for Chlorination of Arenes and Heteroarenes via Catalytic Organic Dye Activation

Heteroarenes and arenes that contain electron-withdrawing groups are chlorinated in good to excellent yields (scalable to gram scale) using trichloroisocyanuric acid (TCCA) and catalytic Brilliant Green (BG). Visible-light activation of BG serves to amplify the electrophilic nature of TCCA, providing a mild alternative approach to acid-promoted chlorination of deactivated (hetero)aromatic substrates. The utility of the TCCA/BG system is demonstrated through comparison to other chlorinating reagents and by the chlorination of pharmaceuticals including caffeine, lidocaine, and phenazone.