121-87-9

Basic information

• Product Name: 2-Chloro-4-nitroaniline
• Synonyms: 2-chloro-4-nitro-anilin;2-chloro-4-nitro-benzenamin;Benzenamine,2-chloro-4-nitro-;LABOTEST-BB LT00030789;2-Chloro-4-nitrobenzenamine;2-CHLORO-4-NITRO-PHENYLAMINE;2-CHLORO-4-NITROANILINE;1-AMINO-2-CHLORO-4-NITROBENZENE
• CAS NO: 121-87-9
• Molecular Formula: C6H5ClN2O2
• Molecular Weight: 172.57
• EINECS: 204-502-2
• Product Categories: Intermediates of Dyes and Pigments;pharmacetical;Functional Materials;Organic Nonlinear Optical Materials
• Mol File: 121-87-9.mol
• Article Data: 39

Chemical Properties

• Melting Point: 107 °C
• Boiling Point: 320℃
• Flash Point: 205 °C
• Appearance: yellow crystalline powder
• Density: 1.5000
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6460 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 0.23g/l
• PKA: -1.05±0.10(Predicted)
• Water Solubility: 0.23 g/L (20 ºC)
• Stability: Stable. Incompatible with strong oxidizing agents, strong bases, strong acids.
• BRN: 638657
• CAS DataBase Reference: 2-Chloro-4-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-nitroaniline(121-87-9)
• EPA Substance Registry System: 2-Chloro-4-nitroaniline(121-87-9)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-51/53
• Safety Statements: 22-24-61
• RIDADR: UN 2237 6.1/PG 3
• WGK Germany: 2
• RTECS: BX1400000
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 121-87-9(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

Uses

Intermediate in manufacture of dyes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 5039, 1986 DOI: 10.1021/jo00375a062

General Description

Yellow crystalline powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Chloro-4-nitroaniline can react with oxidizing materials.

Hazard

Toxic by ingestion and inhalation.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

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

Synthetic route

2-Chlor-4-nitrophenylazid → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
With methyltriphenylphosphonium tetrahydroborate In dichloromethane Reduction; Heating;	100%
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran for 1h; Reduction;	100%
With butyltriphenylphosphonium tetrahydroborate In dichloromethane at 20℃; for 0.0333333h;	98%
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In tetrahydrofuran for 0.58h; Heating;	92%
Stage #1: 2-Chlor-4-nitrophenylazid With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; tert-butyl alcohol In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With sodium t-butanolate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; chemoselective reaction;	86%

3,4-dichloronitrobenzene (99-54-7) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
With ammonium hydroxide; tetrabutylammomium bromide; copper(l) chloride In water at 140℃; under 24002.4 Torr; Reagent/catalyst; Temperature; Pressure;	99.45%
With ethanol; ammonia at 210℃;
With ammonium hydroxide at 160℃;

4-nitro-aniline (100-01-6) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
With sulfuric acid; chlorine at 35℃; under 1500.15 Torr; for 2.5h; Temperature; Flow reactor;	98.4%
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; Reagent/catalyst; Solvent; Temperature; Green chemistry;	98.5%
With sodium periodate; sulfuric acid; sodium dodecyl-sulfate; acetic acid; sodium chloride In water at 25℃; for 1h;	95%

3-Chloronitrobenzene (121-73-3) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
With 4-amino-1,2,4-triazole; potassium tert-butylate In dimethyl sulfoxide for 4h; Ambient temperature;	91%
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h;	86%
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h;	86%

4-nitro-aniline (100-01-6) → 4-nitro-2,6-dichloroaniline (99-30-9) + 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In 1,4-dioxane at 20 - 25℃; Solvent; Green chemistry;	A n/a B 50%
With hydrogenchloride; sodium chlorate In water; acetic acid at 20℃; for 40h;	A 9% B 32%
Chlorierung;
With methanol; chlorine

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;

tert-butylhypochlorite (507-40-4) + 4-nitro-aniline (100-01-6) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
With benzene

N-chloroacetanilide (579-11-3) + 4-nitro-aniline (100-01-6) → Acetanilid (103-84-4) + 2-Chloro-4-nitroaniline (121-87-9)

acetic acid-(2,4,N-trichloro-anilide) (112160-74-4) + 4-nitro-aniline (100-01-6) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
With chloroform

2-amino-5-sulhpoamoylnaphthalene-azo-(2'-chloro-4'-nitrobenzene) (3874-84-8) → 5,6-Diamino-naphthalene-1-sulfonic acid amide (118876-56-5) + 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
In methanol; water Product distribution; potential -300 mV; constant potential coulometry, acid medium; -750 mV in alkaline medium;

4-nitro alcohol → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
With hydrogenchloride; chlorine bei Siedetemperatur;

hydrogenchloride (7647-01-0) + 4-nitro-aniline (100-01-6) + potassium chlorate → 4-nitro-2,6-dichloroaniline (99-30-9) + 2-Chloro-4-nitroaniline (121-87-9)

3,4-dichloronitrobenzene (99-54-7) + ammonia (7664-41-7) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
at 210℃;

N-(2-chlorophenyl)acetamide (533-17-5) + nitric acid (7697-37-2) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → N-(2-chloro-6-nitrophenyl)acetanilide (72487-80-0) + 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
at -5℃; und Behandeln des danach isolierten Reaktionsprodukts mit wss.-aethanol. Kalilauge;

1-chloro-2,4-dinitrobenzene (619-16-9) + ammonia (7664-41-7) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
at 25℃; Kinetics;

1-chloro-2,4-dinitrobenzene (619-16-9) + ammonia (7664-41-7) → 2,4-diaminonitrobenzene (5131-58-8) + 2,5-dinitroaniline (619-18-1) + 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
at 100℃;

N-tosyl-2-chloroaniline (6380-05-8) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; acetic acid; nitric acid 2: aqueous sulfuric acid View Scheme
Multi-step reaction with 2 steps 1: acetic acid; water; nitric acid 2: aqueous sulfuric acid View Scheme

2-Chloroaniline (95-51-2) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous acetic acid 2: acetic acid; acetic acid anhydride; nitric acid / Behandeln des Reaktionsprodukts mit wss.-aethanol.Kalilauge View Scheme

Niclosamide (50-65-7) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
With sodium hydroxide In methanol at 80℃; for 6h; Kinetics; Concentration; Temperature;

1,2-dichloro-benzene (95-50-1) → 2-Chloro-4-nitroaniline (121-87-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; sulfur trioxide; nitric acid / water / 30 - 60 °C 2: tetrabutylammomium bromide; copper(l) chloride; ammonium hydroxide / water / 140 °C / 24002.4 Torr View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / 0 - 5 °C / Green chemistry 2: ammonia / water / Autoclave; Heating; Green chemistry View Scheme

2-Chloro-4-nitroaniline (121-87-9) → 2-chloro-p-phenylenediamine (615-66-7)

Conditions	Yield
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction;	100%
With hydrogen In ethanol; water at 25℃; under 760.051 Torr; for 2.5h; Autoclave;	99.9%
With hydrazine hydrate In ethanol at 85℃; for 4h;	99.2%

2-Chloro-4-nitroaniline (121-87-9) + Acetic formic anhydride (2258-42-6) → 2-chloro-4-nitroformanilide (16135-32-3)

Conditions	Yield
In tetrahydrofuran at 25℃; for 3h;	100%

di-tert-butyl dicarbonate (24424-99-5) + 2-Chloro-4-nitroaniline (121-87-9) → tert-butyl N-[(tert-butoxy)carbonyl]-N-(2-chloro-4-nitrophenyl)carbamate (252019-65-1)

Conditions	Yield
With dmap In tetrahydrofuran at 25℃; for 3h;	100%
With dmap In tetrahydrofuran at 20℃;	100%
With dmap In tetrahydrofuran at 20℃; for 16h;
With dmap In tetrahydrofuran for 1h; Reflux;
With dmap In tetrahydrofuran for 1h; Reflux;

4-methoxy-6-hydroxybenzofuran-5-carboxylic acid (88258-42-8) + 2-Chloro-4-nitroaniline (121-87-9) → 6-hydroxy-4-methoxy-benzofuran-5-carboxylic acid (2-chloro-4-nitro-phenyl)-amide (914485-64-6)

Conditions	Yield
With phosphorus trichloride In chlorobenzene for 3h; Heating;	100%

chloroformic acid ethyl ester (541-41-3) + 2-Chloro-4-nitroaniline (121-87-9) → (2-Chloro-4-nitro-phenyl)-carbamic acid ethyl ester

Conditions	Yield
With magnesium oxide In acetonitrile for 24h; Heating / reflux;	100%

trimethylsilyl ester of hydrocinnamic acid (21273-15-4) + 2-Chloro-4-nitroaniline (121-87-9) → 2'-chloro-4'-nitro-3-phenylpropananilide

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%

2-Chloro-4-nitroaniline (121-87-9) + β-naphthol (135-19-3) → 1-[(2-chloro-4-nitrophenyl)azo]-2-naphthol (2814-77-9)

Conditions	Yield
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Stage #2: β-naphthol In water at 20℃; for 0.666667h;	99%
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Green chemistry; Stage #2: β-naphthol In water at 20℃; for 0.166667h; Green chemistry;	99%
With hydrogenchloride; sodium nitrite 1.) H2O; Multistep reaction;
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride In water at 70℃; for 1h; Stage #2: With sodium nitrite In water for 1.5h; Stage #3: β-naphthol Further stages;

2-Chloro-4-nitroaniline (121-87-9) → 1,2-dibromo-3-chloro-5-nitro-benzene (73557-65-0)

Conditions	Yield
With tert.-butylnitrite; bromine; copper(ll) bromide In acetonitrile at 50℃; for 0.5h;	99%
Multi-step reaction with 2 steps 1: durch Bromierung View Scheme

2-Chloro-4-nitroaniline (121-87-9) → 1,2-bis(2-chloro-4-nitrophenyl)disulfane (20201-04-1)

Conditions	Yield
Stage #1: 2-Chloro-4-nitroaniline With tetrafluoroboric acid; sodium nitrite In water; acetone at -20 - 0℃; for 0.333333h; Stage #2: With carbon disulfide; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In dimethyl sulfoxide at 20℃; for 6h; Concentration; Irradiation;	99%
Multi-step reaction with 2 steps 1: (i) (diazotization), (ii) aq. AcOH, SO2, CuCl2, NaNO3 2: aq. HI View Scheme
Multi-step reaction with 2 steps 1: aqueous H2SO4 / Diazotization.Behandlung der Diazoniumsalz-Loesung mit Kaliumthiocyanat und FeCl3 2: ethanolic (NH4)2 S View Scheme

trimethylsilyl isobutyrate (16883-61-7) + 2-Chloro-4-nitroaniline (121-87-9) → 2'-chloro-2-methyl-4'-nitroapropananilide

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%

3-methylbutyric acid trimethylsilyl ester (55557-13-6) + 2-Chloro-4-nitroaniline (121-87-9) → 2'-chloro-3-methyl-4'-nitroabutananilide

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%

o-benzenedisulfonimide (4482-01-3) + 2-Chloro-4-nitroaniline (121-87-9) → 2-chloro-4-nitrobenzenediazonium o-benzenedisulfonimide

Conditions	Yield
With acetic acid; isopentyl nitrite at 0 - 5℃;	98%

N,N-dimethyl-aniline (121-69-7) + 2-Chloro-4-nitroaniline (121-87-9) → N,N-dimethyl-4-(2-chloro-4-nitrophenylazo)aniline (3150-84-3)

Conditions	Yield
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride In water at 0 - 5℃; for 0.0833333h; Stage #2: N,N-dimethyl-aniline In water for 0.0833333h;	98%
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride In water at 0 - 20℃; for 0.166667h; Stage #2: N,N-dimethyl-aniline In water at 0 - 5℃; for 0.166667h;	86%

2-Chloro-4-nitroaniline (121-87-9) → 1-amino-2-bromo-4-nitro-6-chlorobenzene (99-29-6)

Conditions	Yield
With sodium chlorate; sulfuric acid; hydrogen bromide In water at 35 - 65℃;	97.62%
With acetic acid; potassium bromide In water at 30℃; for 1h;	95%
durch Bromierung;

trimethylsilyl 2,2-dimethylpropionate (37170-49-3) + 2-Chloro-4-nitroaniline (121-87-9) → 2'-chloro-2,2-dimethyl-4'-nitroapropananilide

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%

aniline (62-53-3) + 2-Chloro-4-nitroaniline (121-87-9) → C12H9ClN4O2

Conditions	Yield
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 2.75h; Stage #2: aniline With sodium hydroxide In water at 0 - 5℃; for 3h; pH=6; Concentration; Solvent;	95.7%
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 2.5h; Stage #2: aniline With sodium hydroxide In water at 0 - 5℃; for 3h; pH=6;	94.2%

trimethylsilyl acetate (2754-27-0) + 2-Chloro-4-nitroaniline (121-87-9) → N-(2-chloro-4-nitrophenyl)acetamide (881-87-8)

Conditions	Yield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	95%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	95%

trimethylsilyl 2-methylbenzoate (55557-15-8) + 2-Chloro-4-nitroaniline (121-87-9) → 2'-chloro-2-methyl-4'-nitrobenzanilide

Conditions	Yield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	95%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;	95%

formic acid (64-18-6) + 2-Chloro-4-nitroaniline (121-87-9) → 2-chloro-4-nitroformanilide (16135-32-3)

Conditions	Yield
With 4-(trifluoromethyl)benzoic anhydride; ytterbium(III) triflate In dichloromethane; water for 6h; Heating;	95%

N1-ethyl-N1-(3-methylphenyl)-1,2-ethanediamine (19248-13-6) + 2-Chloro-4-nitroaniline (121-87-9) → C17H20ClN5O2

Conditions	Yield
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride; urea; sodium nitrite In 1,4-dioxane; water at 0 - 5℃; for 2h; Stage #2: N1-ethyl-N1-(3-methylphenyl)-1,2-ethanediamine In 1,4-dioxane at 0 - 5℃; for 3h; pH=6; Solvent;	94.19%

urea (57-13-6) + 1-amino-3-methylbenzene (108-44-1) + 2-Chloro-4-nitroaniline (121-87-9) → C13H11ClN4O2

Conditions	Yield
Stage #1: 2-Chloro-4-nitroaniline With hydrogenchloride In water at 0 - 5℃; for 2.5h; Sonication; Stage #2: urea In water for 0.25h; Stage #3: 1-amino-3-methylbenzene With sodium hydroxide In water at 0 - 5℃; for 4h; pH=6;	92.25%

diethyl 2-ethoxymethylenemalonate (87-13-8) + 2-Chloro-4-nitroaniline (121-87-9) → 2-[(2-Chloro-4-nitro-phenylamino)-methylene]-malonic acid diethyl ester (103976-17-6)

Conditions	Yield
for 1h; Heating;	92%

2-Chloro-4-nitroaniline (121-87-9) → 3-Chloronitrobenzene (121-73-3)

Conditions	Yield
With tetrahydrofuran; tert.-butylnitrite; dimethyl sulfoxide at 30℃; for 1h; Green chemistry;	92%
Stage #1: 2-Chloro-4-nitroaniline With Nitrogen dioxide In acetonitrile at -20℃; Diazotization; Stage #2: With calcium bis(hypophosphite); Fe2SO4*7H2O In methanol; acetonitrile at 20℃; Dediazonation;	87%
With sulfuric acid; ethyl acetate; sodium nitrite In water at 50 - 55℃; for 0.5h;	50%
Multi-step reaction with 3 steps 1: 98 percent / i-pentyl nitrite; HOAc / 0 - 5 °C 2: 91 percent / aq. NaOH / 0.5 h / 0 - 5 °C 3: 9 percent / aq. HBr / acetonitrile / 0.5 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1: 98 percent / i-pentyl nitrite; HOAc / 0 - 5 °C 2: 91 percent / aq. NaOH / 0.5 h / 0 - 5 °C 3: 2 percent / aq. HI; HBF4 / acetonitrile / 0.5 h / 60 °C View Scheme

2-Chloro-4-nitroaniline (121-87-9) + cyclohexanecarbaldehyde (2043-61-0) → N-(2-chloro-4-nitrophenyl)cyclohexanecarboxamide (541533-64-6)

Conditions	Yield
Stage #1: 2-Chloro-4-nitroaniline With tert.-butylnitrite; trimethylsilylazide In tetrahydrofuran at 0℃; Stage #2: cyclohexanecarbaldehyde With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; sodium t-butanolate In tetrahydrofuran at -25℃;	92%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6) + orthoformic acid triethyl ester (122-51-0) + 2-Chloro-4-nitroaniline (121-87-9) → 5-[[(2-chloro-4-nitrophenyl)amino]methylene]-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Conditions	Yield
In butan-1-ol for 4h; Reflux;	91%

4-nitro-benzoyl chloride (122-04-3) + 2-Chloro-4-nitroaniline (121-87-9) → N-(2-chloro-4-nitrophenyl)-4-nitrobenzamide (14105-73-8)

Conditions	Yield
In chlorobenzene at 130 - 132℃; for 2.5h;	90%
With N-ethyl-N,N-diisopropylamine In toluene at 100℃; for 0.5h; Microwave irradiation;	71%

Upstream product

• 619-16-9 1-chloro-2,5-dinitrobenzene 
• 507-40-4 tert-butylhypochlorite 
• 100-01-6 4-nitro-aniline 
• 579-11-3 N-chloroacetanilide 
• 112160-74-4 acetic acid-(2,4,N-trichloro-anilide) 
• 121-73-3 3-Nitrochlorobenzene 
• 99-54-7 3,4-dichloronitrobenzene 
• 7664-41-7 ammonia 
• 881-87-8 N-(2-chloro-4-nitrophenyl)acetamide 
• 533-17-5 N-(2-chlorophenyl)acetamide 
• 95-50-1 1,2-dichloro-benzene 
• 50-65-7 Niclosamide 
• 95-51-2 o-chloroaniline 
• 6380-05-8 N-tosyl-2-chloroaniline 

Downstream Products

• 881-87-8 N-(2-chloro-4-nitrophenyl)acetamide 
• 96461-96-0 N,N'-bis-(2-chloro-4-nitro-phenyl)-urea 
• 121465-04-1 8-chloro-6-nitroquinoline 
• 53393-27-4 (2-Chloro-4-nitro-phenyl)-(2,6-dinitro-4-trifluoromethyl-phenyl)-amine 
• 30359-54-7 4-Nitro-β,β,β,2-tetrachlor-ethylbenzol 
• 57729-84-7 (2-Chloro-4-nitro-phenyl)-(2,4-dinitro-6-trifluoromethyl-phenyl)-amine 
• 68125-14-4 (2-Chloro-4-nitro-phenyl)-(2,4-dinitro-naphthalen-1-yl)-amine 
• 25205-30-5 N,N'-Bis-(2-chlor-4-nitrophenyl)-N',N'''-(4-methylphenyl)-hexandiimidamid 
• 35563-41-8 N-<2-Chlor-4-nitro-phenyl>-2-oxo-cyclopentan-carbonsaeure-(1)-amid 
• 128654-09-1 N-(6-carboxypicolinyl)-2-chloro-4-nitroaniline 
• 114688-43-6 4-Oxo-4H-chromene-2-carboxylic acid (2-chloro-4-nitro-phenyl)-amide 
• 74448-41-2 N-(2-Chloro-4-nitro-phenyl)-2-methylene-succinamic acid 
• 20201-03-0 2-chloro-4-nitrobenzenesulfonyl chloride 
• 178970-18-8 N-(2-Chloro-4-nitro-phenyl)-4-methoxy-benzamide 

Related news

Gas liquid chromatographic analysis of 2-Chloro-4-nitroaniline (cas 121-87-9) on a support based on a non-extractable layer of polyethylene glycol succinate on chromosorb p09/06/2019

Using a non-extractable layer of polyethylene glycol succinate (PEGS) on Chromosorb P, additionally coated with a PEGS stationary phase in a short column, a rapid and successful analysis of 2-chloro-4-nitroaniline was achieved. Chromosorb P AW (0.015% Fe) after coating with PEGS has undergone th...detailed

Mutagenic activity of 2-Chloro-4-nitroaniline (cas 121-87-9) and 5-chlorosalicylic acid in Salmonella typhimurium: two possible metabolites of niclosamide09/05/2019

Niclosamide is an antihelmintic drug susceptible to being metabolized into a bacterial mutagen by the action of enzymes present in the S9 activation mixture. Additional results from genotoxic studies in rodents and humans suggest that the drug is absorbed from the gastrointestinal tract, and mut...detailed

Relevant articles and documents

Kinetic study and mechanism of Niclosamide degradation

A spectrophotometric kinetic study of Niclosamide alkaline degradation as a function of drug concentration, alkaline concentration and temperature has been established utilizing double divisor-ratio spectra spectrophotometric method. The developed method allowed determination of Niclosamide in presence of its alkaline degradation products; namely; 2-chloro-4-nitro aniline (DEG I) and 5-chloro salicylic acid (DEG II) with characterization of its degradation mechanism. It was found that degradation kinetic of Niclosamide followed pseudo-first order under the established experimental conditions with a degradation rate constant (k) of 0.0829 mol/h and half life (t1/2) of 8.35 h. The overall degradation rate constant as a function of the temperature under the given conditions obeyed Arrhenius equation where the activation energy was calculated to be 3.41 kcal/mol.

Sodium lauryl sulfate-catalyzed oxidative chlorination of aromatic compounds

Chlorination of commercially important aromatic compounds using sodium chloride as chlorine source and sodium periodate as oxidant in acidic medium catalyzed by sodium lauryl sulfate (SLS) led to the chloro-substituted aromatics in good yields and purity. Addition of sodium lauryl sulfate led to increased chlorination rate, better yield, excellent purity, and better quality of end product. The advantages of the present method are greater yield, excellent purity, and shorter reaction time at room temperature. Also dichlorinated product can be obtained by increasing the amount of sodium chloride and sodium periodate at slightly higher temperature (40C).

Activator free, expeditious and eco-friendly chlorination of activated arenes by N-chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI)

N-Chloro-N-(phenylsulfonyl)benzene sulfonamide (NCBSI) has been explored for the first time as a chlorinating reagent for direct chlorination of various activated arenes and heterocycles without any activator. A comparative in-silico study was performed to determine the electrophilic character for NCBSI and commercially available N-chloro reagents to reveal the reactivity on a theoretical viewpoint. The reagent was prepared by an improved method avoiding the use of hazardous t-butyl hypochlorite. This reagent was proved to be very reactive compared to other N-chloro reagents. The precursor of the reagent N-(phenylsulfonyl)benzene sulfonamide was recovered from aqueous spent, which can be recycled to synthesize NCBSI. The eco-friendly protocol was equally applicable for the synthesis of industrially important chloroxylenol as an antibacterial agent.

Environment-friendly preparation method of 2-chloro-4-nitro-6-bromoaniline

A preparation method of 2-chloro-4-nitro-6-bromoaniline comprises the following steps: (a) carrying out mixed acid nitration on o-dichlorobenzene, and continuing to apply the generated waste acid to anext nitration reaction; (b) purifying the obtained nitration product in an alcohol solvent to obtain 3,4-dichloronitrobenzene, and continuously applying the recovered alcohol solvent to a next purification process; (c) carrying out ammonolysis on the 3,4-dichloronitrobenzene in a water phase by adopting a specific catalyst to prepare o-chloro-p-nitroaniline, and continuously applying the recycled liquid ammonia to a next ammonolysis reaction; and (d) brominating o-chloro-p-nitroaniline in a hydrogen bromide and oxidant system, and recycling brominated waste acid liquid and bromine for a nextbromination reaction. The product obtained by the method is good in yield, high in purity and high in quality; and two waste acids and bromine in the product are recycled, so that the amount of wastewater is reduced. Compared with traditional processes, the method has obvious quality and environmental protection advantages, and has high production safety.