611-06-3

Basic information

• Product Name: 2,4-Dichloronitrobenzene
• Synonyms: 2,4-DICHLORO-1-NITROBENZENE;2,4-DICHLORONITROBENZENE;ASYM-NITRO-M-DICHLOROBENZENE;4-Nitro-m-dichlorobenzene;2,4-DICHLORONITROBENZENE PESTANAL, 250 M;2,4-DCNB;Benzene, 2,4-dichloro-1-nitro-;1,3-Dichlor-4-nitrobenzol
• CAS NO: 611-06-3
• Molecular Formula: C₆H₃Cl₂NO₂
• Molecular Weight: 192
• EINECS: 210-248-3
• Product Categories: Chlorobenzene Series;Benzene derivates;Building Blocks;Chemical Synthesis;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 611-06-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 29-32 °C(lit.)
• Boiling Point: 258 °C(lit.)
• Flash Point: >230 °F
• Appearance: Yellow-brown/Crystalline Low Melting Solid
• Density: 1.479
• Vapor Pressure: 0.0221mmHg at 25°C
• Refractive Index: 1.5512 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 188g/l
• Water Solubility: 188 mg/L (20 ºC)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
• BRN: 1451655
• CAS DataBase Reference: 2,4-Dichloronitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloronitrobenzene(611-06-3)
• EPA Substance Registry System: 2,4-Dichloronitrobenzene(611-06-3)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-51/53-43-21/22
• Safety Statements: 26-36-61-36/37-24
• RIDADR: 2811
• WGK Germany: 3
• RTECS: CZ5420000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 611-06-3(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystals

Uses

2,4-Dichloro-1-nitrobenzene is used as a reagent in the synthesis of the hepatitis C virus polymerase inhibitor, Deleobuvir (BI 207127).

General Description

Light yellow needles or amber crystalline solid.

Air & Water Reactions

Insoluble in water.

Fire Hazard

2,4-Dichloronitrobenzene is combustible.

Synthetic route

1,3-Dichlorobenzene (541-73-1) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
With sulfuric acid; nitric acid at 10 - 15℃; for 3h; Temperature;	97.2%
With sulfuric acid; nitric acid at 60℃; for 1h;	95.4%
With nitric acid; acetic anhydride In tetrachloromethane	65.3%

5-chloro-2-nitrobenzoic acid (2516-95-2) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
With copper(l) iodide; oxygen; copper(l) chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 30h; Schlenk technique; Sealed tube;	93%
With oxygen; silver carbonate; potassium hydroxide; copper dichloride In dimethyl sulfoxide; N,N-dimethyl-formamide at 130 - 140℃;	80%
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique;	66%
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper diacetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 20h; Schlenk technique;	64%

2,4-dichlorophenylboronic acid (68716-47-2) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
With zirconium(IV) oxynitrate hydrate; iodine In toluene at 20℃; for 18h; Inert atmosphere;	85%

2,4-Dichloroaniline (554-00-7) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
With sulfuric acid; acetic acid; tetra-n-propylammonium bromate for 1.5h; Heating;	81%
With tert.-butylhydroperoxide; potassium iodide In water; acetonitrile at 80℃; for 15h;	52%
Multi-step reaction with 2 steps 1: ethyl nitrite 2: durch Nitrieren View Scheme
Multi-step reaction with 2 steps 1: ethyl nitrite 2: water; nitric acid View Scheme

aniline hydrochloride (142-04-1) → 2,4-dichloronitrobenzene (611-06-3) + 4-chlorobenzonitrile (100-00-5) + 2-Chloronitrobenzene (88-73-3)

Conditions	Yield
With 3,3-dimethyldioxirane In acetone at 20℃;	A 12% B 36% C 23%

2,6-dichloro-3-nitrobenzaldehyde (5866-97-7) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
With potassium hydroxide at 100℃;

2,6-dichloro-3-nitroaniline (13785-48-3) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
With ethyl nitrite; ethanol

2-nitro-3,5-dichloroacetanilide (342043-37-2) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
With sulfuric acid at 110℃; Kochen des Reaktionsgemisches mit NaNO2 in Aethanol;

2-Chloronitrobenzene (88-73-3) → 2,4-dichloronitrobenzene (611-06-3) + 1,2-Dichloro-3-nitrobenzene (3209-22-1)

Conditions	Yield
With antimonypentachloride beim Chlorieren;

nitrobenzene (98-95-3) → 2,4-dichloronitrobenzene (611-06-3) + 3-Chloronitrobenzene (121-73-3) + Quintozene (82-68-8) + 2-Chloronitrobenzene (88-73-3)

Conditions	Yield
With chlorine fluorosulfate In 1,1,2-Trichloro-1,2,2-trifluoroethane at -25℃;	A 16.5 % Chromat. B 8.5 % Chromat. C 2 g D 2.8 % Chromat.

1,3-Dichlorobenzene (541-73-1) → 2,4-dichloronitrobenzene (611-06-3) + 3,5-dichloro-1-nitrobenzene (618-62-2) + 2,6-dichloronitrobenzene (601-88-7)

Conditions	Yield
With Nitrogen dioxide; ozone In dichloromethane at 0 - 5℃; for 1h; Yield given;
With Nitrogen dioxide; ozone In dichloromethane at 0 - 5℃; for 1h; Yield given. Yields of byproduct given;

5-chloro-2-nitroaniline (1635-61-6) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
(i) (diazotization), (ii) CuCl; Multistep reaction;

antimonypentachloride (7647-18-9) + 2-Chloronitrobenzene (88-73-3) → 2,4-dichloronitrobenzene (611-06-3) + 2,5-dichloronitrobenzene (89-61-2) + 2.3-dichloro-1-nitrobenzene

Conditions	Yield
at 100℃; durch Chlorierung;

nitric acid (7697-37-2) + 1,3-Dichlorobenzene (541-73-1) → 2,4-dichloronitrobenzene (611-06-3)

nitric acid (7697-37-2) + 1,3-Dichlorobenzene (541-73-1) → 2,4-dichloronitrobenzene (611-06-3) + 2,6-dichloronitrobenzene (601-88-7)

2,6-dichloro-3-nitrobenzaldehyde (5866-97-7) + aqueous KOH-solution → formic acid (64-18-6) + 2,4-dichloronitrobenzene (611-06-3)

diazotized 2-nitro-5-chloro-aniline → 2,4-dichloronitrobenzene (611-06-3) + 5,5'-dichloro-2,2'-dinitro-1,1'-biphenyl (19036-42-1)

Conditions	Yield
With hydrogenchloride; copper dichloride

3-nitro-aniline (99-09-2) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; calcium hypochlorite / 40 - 60 °C 2: ethyl nitrite; absolute alcohol View Scheme

3-Chloronitrobenzene (121-73-3) → 2,4-dichloronitrobenzene (611-06-3) + 2,6-dichloronitrobenzene (601-88-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorine / 190 °C / Large scale 2: sulfuric acid; nitric acid / 135 °C / Large scale View Scheme

1,3-Dichlorobenzene (541-73-1) → 2,4-dichloronitrobenzene (611-06-3) + 2,6-dichloronitrobenzene (601-88-7)

Conditions	Yield
With sulfuric acid; nitric acid at 135℃; Temperature; Large scale; Overall yield = 525.2 kg;

C8H8ClNO3 → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
With 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; silver(l) oxide In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 36h; Autoclave;	62 %Chromat.

5-chloro-2-nitroacetophenone (18640-60-3) → 2,4-dichloronitrobenzene (611-06-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0 °C 2: potassium carbonate; copper dichloride; 1,10-Phenanthroline; oxygen; silver(l) oxide / dimethyl sulfoxide / 36 h / 140 °C / 3750.38 Torr / Autoclave View Scheme

2,4-dichloronitrobenzene (611-06-3) → 2,4-Difluoronitrobenzene (446-35-5)

Conditions	Yield
With trihexyl (tetradecyl) phosphonium tetrafluoroborate; potassium fluoride In dimethyl sulfoxide at 180℃; for 1.8h;	100%
With potassium fluoride; bis(tricyclohexylphosphine)nickel(II) dichloride; tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 150℃; for 8h; Inert atmosphere;	99.3%
With potassium fluoride In sulfolane; methanol at 100 - 180℃; for 8h; Product distribution / selectivity;	90%

2,4-dichloronitrobenzene (611-06-3) + methylamine (74-89-5) → 4-chloro-2-methylaminonitrobenzene (35966-84-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 40℃; for 22h; Product distribution / selectivity;	100%
With triethylamine In tetrahydrofuran at 40℃; for 22h; Inert atmosphere;	100%
In water; dimethyl sulfoxide at 27 - 37℃; for 6h;	90%

2,4-dichloronitrobenzene (611-06-3) → 2,4-Dichloroaniline (554-00-7)

Conditions	Yield
With hydrogen In ethanol; water at 25℃; under 760.051 Torr; for 3h; Autoclave;	99.9%
With hydrogen In tetrahydrofuran; water at 120℃; under 22502.3 Torr; for 4h; Autoclave;	99%
Stage #1: 2,4-dichloronitrobenzene With 2.0%Pt-0.5%Rh/C In methanol for 0.0833333h; Stage #2: With hydrogen In methanol at 30℃; under 760.051 Torr; for 2.5h; Catalytic behavior; Reagent/catalyst;	98.9%

2,4-dichloronitrobenzene (611-06-3) + 1-amino-3-(dimethylamino)propane (109-55-7) → N1-(5-chloro-2-nitrophenyl)-N3,N3-dimethylpropane-1,3-diamine (92547-10-9)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Inert atmosphere; Reflux;	97%
With potassium carbonate In acetonitrile for 24h; Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;	97%
at 100℃; for 3h; Neat (no solvent);	97%

2,4-dichloronitrobenzene (611-06-3) + 2,4-dichlorophenol (120-83-2) → 2,4-bis(2,4-dichlorophenoxy)-nitrobenzene (57532-59-9)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 140℃; for 8.5h;	96.5%

2,4-dichloronitrobenzene (611-06-3) → 2,4,5-Trichloronitrobenzene (89-69-0)

Conditions	Yield
With N-chloro-succinimide; acetic acid at 8℃; Large scale;	96%
With antimonypentachloride durch Chlorierung;

2,4-dichloronitrobenzene (611-06-3) + p-Chlorothiophenol (106-54-7) → 2,4-bis[(4-chlorophenyl)thio]-1-nitrobenzene

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 1h; Sonication;	96%

2,4-dichloronitrobenzene (611-06-3) + ethanolamine (141-43-5) → 2-<(5-chloro-2-nitro)phenylamino>ethanol (50610-29-2)

Conditions	Yield
In ethanol at 75 - 80℃; for 4h;	95%
With potassium carbonate In ethanol Reflux;	89%
With potassium carbonate In butan-1-ol Heating;	84%

2,4-dichloronitrobenzene (611-06-3) + 4-amino-2-(methylthio)pyrimidine (2183-66-6) → C11H9ClN4O2S (1429658-37-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃;	95%

2,4-dichloronitrobenzene (611-06-3) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-(5-chloro-2-nitrophenyl)-2-cyanoacetate (62567-91-3)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; palladium diacetate; sodium carbonate; 1,2-bis-(diphenylphosphino)ethane; potassium iodide In N,N-dimethyl-formamide at 130℃; for 22h; Inert atmosphere;	93%
(i) NaOEt, DMSO, (ii) /BRN= 1451655/; Multistep reaction;
With potassium tert-butylate In tetrahydrofuran for 48h; Reflux;

2,4-dichloronitrobenzene (611-06-3) + 9-Phenylfluorene (789-24-2) → 9-(3-chloro-4-nitrophenyl)-9-phenylfluorene (124233-18-7)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dimethyl sulfoxide at 45 - 50℃; for 4h;	92%

N-methylcyclohexylamine (626-67-5) + 2,4-dichloronitrobenzene (611-06-3) → 2-chloro-4-piperidinonitrobenzene

Conditions	Yield
In tetrahydrofuran at 80℃; under 5625450 Torr; for 20h;	91.9%

2,4-dichloronitrobenzene (611-06-3) + thiophenol (108-98-5) → 2-chloro-4-phenylthio nitrobenzene

Conditions	Yield
With potassium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Solvent; Reagent/catalyst; Reflux;	91.4%

2,4-dichloronitrobenzene (611-06-3) + malonic acid dimethyl ester (108-59-8) → 2-(4-chloro-2-nitro-phenyl)-malonic acid dimethyl ester (582305-49-5)

Conditions	Yield
Stage #1: malonic acid dimethyl ester With sodium hydride In 1-methyl-pyrrolidin-2-one at 30℃; Stage #2: 2,4-dichloronitrobenzene In 1-methyl-pyrrolidin-2-one at 65℃;	91%

2,4-dichloronitrobenzene (611-06-3) + 1-(1-chloroethyl)phenyl sulfone (13557-25-0) → 1-(3,5-dichloro-2-nitrophenyl)ethyl phenyl sulphone (117508-91-5)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at -40 - -30℃;	90%

2,4-dichloronitrobenzene (611-06-3) + diethylamine (109-89-7) → N,N-diethyl-5-chloro-2-nitro-aniline (133387-29-8) + N1,N1,N3,N3-Tetraethyl-4-nitro-benzene-1,3-diamine (133387-32-3)

Conditions	Yield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h;	A 90% B 10%

pyrrolidine (123-75-1) + 2,4-dichloronitrobenzene (611-06-3) → 4-chloro-2-(1-pyrrolidinyl)nitrobenzene (133387-30-1)

Conditions	Yield
With potassium hydrogencarbonate; cobalt(II) chloride In para-xylene at 140℃; for 1h; Inert atmosphere; regioselective reaction;	90%

2,4-dichloronitrobenzene (611-06-3) + thiophenol (108-98-5) → 2-nitro-5-phenylthioaniline (43156-47-4)

Conditions	Yield
With ammonia In isopropyl alcohol	89.5%

pyrrolidine (123-75-1) + 2,4-dichloronitrobenzene (611-06-3) → 2-chloro-4-(1-pyrrolidinyl)nitrobenzene (133387-31-2) + 4-chloro-2-(1-pyrrolidinyl)nitrobenzene (133387-30-1) + 2,4-di(1-pyrrolidinyl)nitrobenzene (133387-33-4)

Conditions	Yield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h;	A 3% B 89% C 2%

2,4-dichloronitrobenzene (611-06-3) + 2-Mercaptobenzothiazole (149-30-4) → 2-(3-Chloro-4-nitro-phenylsulfanyl)-benzothiazole

Conditions	Yield
With potassium hydroxide In ethanol for 2h; Heating;	89%

2,4-dichloronitrobenzene (611-06-3) + p-Chlorothiophenol (106-54-7) → 4-chloro-2-(4-chlorophenylthio)nitrobenzene (105945-59-3)

Conditions	Yield
With potassium carbonate In m-xylene at 160℃; for 15h;	89%

2,4-dichloronitrobenzene (611-06-3) + n-Octylamine (111-86-4) → N-octyl-2-nitro-5-chloroaniline (1156057-44-1)

Conditions	Yield
In dimethyl sulfoxide at 20 - 60℃; Inert atmosphere;	88%

2,4-dichloronitrobenzene (611-06-3) → aniline (62-53-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrazine hydrate In methanol at 120℃; for 0.25h; Microwave irradiation;	88%

morpholine (110-91-8) + 2,4-dichloronitrobenzene (611-06-3) → 4-(3-chloro-4-nitrophenyl)morpholine (65976-65-0) + 4-(5-chloro-2-nitrophenyl)morpholine (65976-63-8) + 4-[3-(morpholin-4-yl)-4-nitrophenyl]morpholine (133387-34-5)

Conditions	Yield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h;	A 2% B 86% C 11%

2,4-dichloronitrobenzene (611-06-3) → 5-chlorobenzofurazan-1-oxide (17348-69-5)

Conditions	Yield
With sodium azide; N-ethyl-N-methylpyrrolidinium tetrafluoroborate; tetrabutylammomium bromide In water at 110℃; for 8h;	86%

1,2,3,4-tetrahydroisoquinoline (91-21-4) + 2,4-dichloronitrobenzene (611-06-3) → 9-chloro-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline

Conditions	Yield
at 130℃; for 24h; Inert atmosphere;	86%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 2,4-dichloronitrobenzene (611-06-3) → 1-(2,4-dichlorophenyl)-1H-pyrrole (383137-35-7)

Conditions	Yield
With tin(II) chloride dihdyrate In water at 55℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Green chemistry;	86%
With tin(II) chloride dihdyrate In water at 55℃; for 0.5h; Reagent/catalyst; Solvent;	85%

2,4-dichloronitrobenzene (611-06-3) + sodium methylate (124-41-4) → 3-chloro-4-nitroanisole (28987-59-9)

Conditions	Yield
In methanol at 68℃;	85.5%

Upstream product

• 5866-97-7 2,6-dichloro-3-nitrobenzaldehyde 
• 541-73-1 1,3-Dichlorobenzene 
• 98-95-3 nitrobenzene 
• 7697-37-2 nitric acid 
• 88-73-3 2-Chloronitrobenzene 
• 13785-48-3 2,6-dichloro-3-nitroaniline 
• 18640-60-3 5-chloro-2-nitroacetophenone 
• 121-73-3 3-Nitrochlorobenzene 
• 68716-47-2 2,4-dichlorophenylboronic acid 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 99-09-2 3-nitro-aniline 
• 554-00-7 2,4-Dichloroaniline 
• 142-04-1 aniline hydrochloride 
• 7647-18-9 antimonypentachloride 

Downstream Products

• 32816-66-3 N-(5-chloro-2-nitrophenyl)-N-(4-chlorophenyl)amine 
• 50610-29-2 2-<(5-chloro-2-nitro)phenylamino>ethanol 
• 133387-29-8 N,N-diethyl-5-chloro-2-nitro-aniline 
• 78213-37-3 1-(5-chloro-2-nitro-anilino)-propan-2-ol 
• 56223-80-4 N'-(5-chloro-2-nitrophenyl)-N,N-diethyl-ethane-1,2-diamine 
• 28093-68-7 (5-chloro-2-nitro-phenyl)-(3-chloro-phenyl)-amine 
• 162140-41-2 (5-chloro-2-nitro-phenyl)-(2-chloro-phenyl)-amine 
• 254747-56-3 3-(5-chloro-2-nitrophenylamino)-1-propanol 
• 62597-54-0 2-(3-Chloro-4-nitro-phenyl)-1,2-diphenyl-ethanone 
• 62567-93-5 2-(5-Chloro-2-nitro-phenyl)-1,2-diphenyl-ethanone 
• 62567-88-8 5,7-dichloro-3-phenyl-benzo[c]isoxazole 
• 32861-89-5 C₁₅H₉Cl₂NO₄ 
• 32861-88-4 C₁₅H₁₁Cl₂NO₄ 
• 62567-91-3 ethyl 2-(5-chloro-2-nitrophenyl)-2-cyanoacetate 

Relevant articles and documents

Novel preparation method of 2, 4, 5-trifluorophenylacetic acid

The invention discloses a novel preparation method of 2, 4, 5-trifluorophenylacetic acid, which belongs to the technical field of preparation of medical intermediates, and comprises the following preparation steps: carrying out nitration reaction on sulfuric acid and m-dichlorobenzene to obtain an intermediate II; adding the intermediate II, a phase transfer catalyst and potassium fluoride into an aprotic solvent to obtain an intermediate III; performing hydrogenation reaction on the intermediate III to obtain an intermediate IV; carrying out diazotization reaction on the intermediate IV, nitrosyl sulfuric acid and sodium fluoborate to obtain an intermediate V; performing cracking reaction on the intermediate V to obtain an intermediate VI; carrying out reduction reaction on the intermediate VI, and then carrying out bromination reaction on the intermediate VI and liquid bromine to obtain an intermediate VII; subjecting the intermediate VII to a substitution reaction with diethyl malonate, and obtaining 2, 4, 5-trifluorophenylacetic acid after hydrolysis and purification. A novel synthesis route is provided, the problem that technological operation is tedious is solved, the requirements for reaction and operation conditions are low, anhydrous and oxygen-free reaction conditions are not needed, the method is suitable for industrial production, and the yield and purity are greatly improved.

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The method is characterized by comprising the following steps: taking m-chloronitrobenzene as a raw material, carrying out high-temperature chlorination reaction, nitration reaction and fluorination reaction to obtain 2,4 - 2,4 -difluorobenzene and carrying out a methoxylation reaction with m-difluorobenzene as a raw material and carrying out methoxylation reaction to obtain m-fluorobenzyl ether; and the hydrogenation catalyst is a porous alumina loaded NiO-Co222O3-MoOO3 composite catalyst. The method disclosed by the invention is simple in process and high in product yield. (by machine translation)