3209-22-1

Basic information

• Product Name: 2,3-Dichloronitrobenzene
• Synonyms: 1,2-dichloro-3-nitro-benzen;2,3-Dichloro-1-nitrobenzene;3-nitro-o-dichlorobenzene;1,2-DICHLORO-3-NITROBENZENE;2,3-DICHLORONITROBENZENE;2,3-DICHLORONITROBENZENE PESTANAL, 250 M;1,2-Dichloro-3-nitrobenzene,97%;1,2-dichlor-3-nitrobenzene
• CAS NO: 3209-22-1
• Molecular Formula: C₆H₃Cl₂NO₂
• Molecular Weight: 192
• EINECS: 221-717-7
• Product Categories: alkyl chloride| nitro-compound
• Mol File: 3209-22-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 60 °C
• Boiling Point: 270 °C
• Flash Point: 255 °F
• Appearance: light yellow to light brown crystalline powder
• Density: 1.449 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0233mmHg at 25°C
• Refractive Index: 1.5929 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 66.8mg/l
• Water Solubility: 67 mg/L
• BRN: 2048029
• CAS DataBase Reference: 2,3-Dichloronitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dichloronitrobenzene(3209-22-1)
• EPA Substance Registry System: 2,3-Dichloronitrobenzene(3209-22-1)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-51/53-20/22
• Safety Statements: 60-61-37
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: CZ5240000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 3209-22-1(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to light brown crystalline powder

General Description

Light yellow crystals or yellow crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Can react vigorously with oxidizing materials.

Health Hazard

ACUTE/CHRONIC HAZARDS: 2,3-Dichloronitrobenzene may cause irritation on contact.

Fire Hazard

2,3-Dichloronitrobenzene is combustible.

InChI:InChI=1/C6H3Cl2NO2/c7-4-2-1-3-5(6(4)8)9(10)11/h1-3H

Synthetic route

2,3-dichlorobenzeneboronic acid (151169-74-3) → 1,2-Dichloro-3-nitrobenzene (3209-22-1)

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; 2-nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide at 60℃; for 19h; Inert atmosphere; Schlenk technique;	96%

1,2-dichloro-benzene (95-50-1) → 3,4-dichloronitrobenzene (99-54-7) + 1,2-Dichloro-3-nitrobenzene (3209-22-1)

Conditions	Yield
With nitric acid at 50℃; for 3h;	A 90.2% B 9.8%
With Iron(III) nitrate nonahydrate; phosphorus pentoxide In neat (no solvent) at 20℃; for 6h; Milling; Green chemistry;	A 87% B 13%
With Nitrogen dioxide; ozone In dichloromethane at 0 - 5℃; for 2h; Product distribution; reactions of polyhalogenobenzenes under var. conditions;

2,3-dinitroaniline (602-03-9) → 1,2-Dichloro-3-nitrobenzene (3209-22-1)

Conditions	Yield
With hydrogenchloride; copper(l) chloride Diazotization;
Diazotization.Behandeln mit Kupfer(I)-chlorid;
(i) NaNO2, aq. HCl, (ii) CuCl, Cu, aq. HCl; Multistep reaction;

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;

2-chloro-6-nitroaniline (769-11-9) → 1,2-Dichloro-3-nitrobenzene (3209-22-1)

Conditions	Yield
(i) NaNO2, aq. HCl, (ii) CuCl, aq. HCl; Multistep reaction;

3-Chloronitrobenzene (121-73-3) → 3,4-dichloronitrobenzene (99-54-7) + 1,2-Dichloro-3-nitrobenzene (3209-22-1) + 2,5-dichloronitrobenzene (89-61-2)

Conditions	Yield
With chlorine; iron(III) chloride at 90℃; Product distribution; relative rates;

nitrobenzene (98-95-3) → 3,4-dichloronitrobenzene (99-54-7) + 3-Chloronitrobenzene (121-73-3) + 1,2-Dichloro-3-nitrobenzene (3209-22-1) + 4-chlorobenzonitrile (100-00-5) + 2-Chloronitrobenzene (88-73-3) + 2,5-dichloronitrobenzene (89-61-2)

Conditions	Yield
With chlorine; iron(III) chloride at 60 - 120℃; Product distribution; Kinetics; relative rates of each steps;

2-Chloronitrobenzene (88-73-3) → 1,2-Dichloro-3-nitrobenzene (3209-22-1) + 1-chloro-2,6-dinitrobenzene (606-21-3) + 1-chloro-2,4-dinitro-benzene (97-00-7) + 2,5-dichloronitrobenzene (89-61-2)

Conditions	Yield
With hydrogenchloride; sulfuric acid; nitric acid at 25℃; Product distribution;	A 0.2 % Chromat. B 6.7 % Chromat. C 94.8 % Chromat. D 0.3 % Chromat.

2-Chloronitrobenzene (88-73-3) → 1,2-Dichloro-3-nitrobenzene (3209-22-1) + 2,5-dichloronitrobenzene (89-61-2)

Conditions	Yield
With chlorine; iron(III) chloride at 90℃; Product distribution; relative rates;

nitric acid (7697-37-2) + 1,2-dichloro-benzene (95-50-1) → 3,4-dichloronitrobenzene (99-54-7) + 1,2-Dichloro-3-nitrobenzene (3209-22-1)

Conditions	Yield
at 0℃;

sulfuric acid (7664-93-9) + nitric acid (7697-37-2) + 1,2-dichloro-benzene (95-50-1) → 3,4-dichloronitrobenzene (99-54-7) + 1,2-Dichloro-3-nitrobenzene (3209-22-1)

Conditions	Yield
at 60℃;

antimony(III) chloride (10025-91-9) + chlorine (7782-50-5) + nitrobenzene (98-95-3) → 1,2-Dichloro-3-nitrobenzene (3209-22-1) + 2-Chloronitrobenzene (88-73-3) + 2,5-dichloronitrobenzene (89-61-2)

2-Chloronitrobenzene (88-73-3) → 1,2-Dichloro-3-nitrobenzene (3209-22-1) + 2.4-dichloro-1-nitro-benzene; 2.5-dichloro-1-nitro-benzene

Conditions	Yield
With antimonypentachloride beim Chlorieren;

3-Chloronitrobenzene (121-73-3) + antimony chloride → 1,2-Dichloro-3-nitrobenzene (3209-22-1) + 2,5-dichloronitrobenzene (89-61-2)

Conditions	Yield
bei der Chlorierung;

N-(3-nitrophenyl)acetanilide (122-28-1) → 1,2-Dichloro-3-nitrobenzene (3209-22-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: HNO3, H2SO4 2: H2SO4 / 110 °C 3: (i) NaNO2, aq. HCl, (ii) CuCl, Cu, aq. HCl View Scheme

N-(2,3-dinitrophenyl)acetamide (60956-27-6) → 1,2-Dichloro-3-nitrobenzene (3209-22-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4 / 110 °C 2: (i) NaNO2, aq. HCl, (ii) CuCl, Cu, aq. HCl View Scheme

2-Chloroaniline (95-51-2) → 1,2-Dichloro-3-nitrobenzene (3209-22-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) Ac2O, (ii) HNO3, (iii) aq. H2SO4 2: (i) NaNO2, aq. HCl, (ii) CuCl, aq. HCl View Scheme

pyrrolidine (123-75-1) + 1,2-Dichloro-3-nitrobenzene (3209-22-1) → 1-(2-chloro-6-nitrophenyl)pyrrolidine (59504-30-2)

Conditions	Yield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h;	100%

morpholine (110-91-8) + 1,2-Dichloro-3-nitrobenzene (3209-22-1) → 4-(2-chloro-6-nitro-phenyl)-morpholine (65152-10-5)

Conditions	Yield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h;	100%

1,2-Dichloro-3-nitrobenzene (3209-22-1) → 2,3-dichloroaniline (608-27-5)

Conditions	Yield
With hydrogen In ethanol; water at 25℃; under 760.051 Torr; for 3h; Autoclave;	99.9%
With BiFeO3; isopropyl alcohol; potassium hydroxide for 2.66667h; Heating;	97%
With nickel(II) oxide; ethanol; potassium hydroxide for 1.33333h; Reflux;	96%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + ethanolamine (141-43-5) → 2-(2-chloro-6-nitro-anilino)-ethanol (65976-54-7)

Conditions	Yield
In ethanol for 20h; Heating / reflux;	99%
With butan-1-ol

1,2-Dichloro-3-nitrobenzene (3209-22-1) + 2-methyl 6-mercapto aniline (76462-17-4) → 2-(2-chloro-6-nitro-phenylsulfanyl)-6-methyl-phenylamine (500898-54-4)

Conditions	Yield
With sodium acetate In ethanol for 3h; Heating;	99%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + diethylamine (109-89-7) → N,N-diethyl-2-chloro-6-nitro-aniline (133387-28-7)

Conditions	Yield
In tetrahydrofuran at 50℃; under 4500360 Torr; for 20h;	98%
With methanol at 150℃; Kinetik der Reaktion bei 85grad und 110grad;

1,2-Dichloro-3-nitrobenzene (3209-22-1) → 2-chloro-6-nitrobenzonitrile (6575-07-1)

Conditions	Yield
In N,N-dimethyl-formamide	98%
In N,N-dimethyl-formamide	97%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + tert-butylamine (75-64-9) → N-tert-butyl-6-chloro-2-nitroaniline (148858-01-9)

Conditions	Yield
In ethanol at 150℃; for 72h;	97%
In ethanol at 150℃; for 72h;	90%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + 1-amino-3-(dimethylamino)propane (109-55-7) → N1-(2-chloro-6-nitrophenyl)-N3,N3-dimethylpropane-1,3-diamine

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Inert atmosphere; Reflux;	96%
With potassium carbonate In acetonitrile for 16h; Reflux; Inert atmosphere;	96%
In toluene

propylamine (107-10-8) + 1,2-Dichloro-3-nitrobenzene (3209-22-1) → (2-chloro-6-nitro-phenyl)-propyl-amine (1072928-95-0)

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 1.5h; Product distribution / selectivity;	96%
In dimethyl sulfoxide at 100℃; for 1.5h; Product distribution / selectivity;	96%
In N,N-dimethyl acetamide at 0 - 100℃; for 3h; Product distribution / selectivity;	93%
In N,N-dimethyl acetamide at 0 - 100℃; for 3h; Product distribution / selectivity;	93%

1,2-Dichloro-3-nitrobenzene (3209-22-1) → 6-chloro-2-nitrothiophenol (14371-77-8)

Conditions	Yield
Stage #1: 1,2-Dichloro-3-nitrobenzene With sodium sulfide In dimethyl sulfoxide at 20℃; for 18h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide pH=4;	95%
With sodium sulfide In carbon disulfide; butanone for 12h; Ambient temperature;	80%
With sodium sulfide; ethanol; sulfur

1,2-Dichloro-3-nitrobenzene (3209-22-1) + toluene-4-sulfonamide (70-55-3) → N-(2-chloro-6-nitrophenyl)-4-methylbenzenesulfonamide (1620787-21-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 0.2h; Microwave irradiation;	95%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + 1,3-dihydro-imidazole-2-thione (872-35-5) → 2-(2-chloro-6-nitrophenylthio)imidazole (683276-68-8)

Conditions	Yield
With potassium carbonate In acetonitrile for 6.5h; Heating / reflux;	94%

1,2-Dichloro-3-nitrobenzene (3209-22-1) → N-(2,3-dichlorophenyl)hydroxylamine (43192-06-9)

Conditions	Yield
With hydrogen; platinum In 4-methyl-morpholine; cyclohexane	93.3%
With hydrazine; palladium on activated charcoal In tetrahydrofuran; ethanol
With water; ammonium chloride; zinc In ethanol at 70℃;

1,2-Dichloro-3-nitrobenzene (3209-22-1) → 1,2,3-trichlorobenzene (87-61-6)

Conditions	Yield
With Dichlorophenylphosphine In various solvent(s) at 170℃; for 5h;	93%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + 4-Chlorophenylboronic acid (1679-18-1) → 2-nitro 6,4'-dichlorobiphenyl

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 10h; Inert atmosphere; Reflux;	93%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + 1-(tetrahydro-2H-pyran-2-yl)-1,2-dihydro-3H-indazol-3-one → 3-(2-chloro-6-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; caesium carbonate at 50℃; for 16h; Inert atmosphere;	92.8%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + phenylmethanethiol (100-53-8) → 2-(benzylsulfanyl)-1-chloro-3-nitrobenzene (178551-28-5)

Conditions	Yield
With sodium In ethanol for 1.08333h; Reflux;	91%

1,2-Dichloro-3-nitrobenzene (3209-22-1) → 1-chloro-2-fluoro-3-nitrobenzene (2106-49-2)

Conditions	Yield
With potassium fluoride at 140 - 150℃; for 3h; Reagent/catalyst;	87.6%
With calcium fluoride; potassium fluoride In sulfolane at 150℃; for 96h;	48.5%
With potassium fluoride; N,N-dimethyl-formamide at 150℃;
With potassium fluoride In 5,5-dimethyl-1,3-cyclohexadiene
With potassium fluoride; tetramethlyammonium chloride

1,2-Dichloro-3-nitrobenzene (3209-22-1) → 2-chloro-6-nitroaniline (769-11-9)

Conditions	Yield
With ammonium hydroxide In ethanol at 100℃; for 24h; Autoclave;	87%
With ammonia In ethanol at 140℃; for 30h;	86%
With ethanol; ammonia at 180℃;

dibromodifluoromethane (75-61-6) + 1,2-Dichloro-3-nitrobenzene (3209-22-1) → 1,2-Bis(trifluoromethyl)-3-nitrobenzene (1978-06-9) + 1-chloro-3-nitro-2-(trifluoromethyl)nicotinate (133391-58-9)

Conditions	Yield
With ISOPROPYLAMIDE; copper at 100℃; for 5h;	A 5% B 86%

1,2-Dichloro-3-nitrobenzene (3209-22-1) → 2-chloro-6-nitrophenol (603-86-1)

Conditions	Yield
With potassium hydroxide In methanol; water for 43h; Heating;	86%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-(2-chloro-6-nitrophenyl)-2-cyanoacetate (1126602-43-4)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 48h; Reflux;	86%
Stage #1: ethyl 2-cyanoacetate With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.25h; Stage #2: 1,2-Dichloro-3-nitrobenzene In tetrahydrofuran for 48h; Heating / reflux;
With potassium tert-butylate In tetrahydrofuran for 48h; Inert atmosphere; Reflux;

1,2-Dichloro-3-nitrobenzene (3209-22-1) + 3-bromo-5-chlorophenol (56962-04-0) → 2-(3-bromo-5-chlorophenoxy)-1-chloro-3-nitrobenzene (1034474-41-3)

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 2h; Inert atmosphere;	85.4%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 2h;

1,2-Dichloro-3-nitrobenzene (3209-22-1) + sodium methylate (124-41-4) → 1-chloro-2-methoxy-3-nitro-benzene (80866-77-9)

Conditions	Yield
With diisopropylamine In methanol at 60℃; for 5h; Temperature; Solvent;	85%
With methanol Kinetik dieser Reaktion bei 85grad und 110grad;

1,2-Dichloro-3-nitrobenzene (3209-22-1) + phenylboronic acid (98-80-6) → 2-chloro-6-nitro-1,1'-biphenyl (140665-55-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 20 - 90℃; for 15h; Inert atmosphere;	84%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 80℃; for 15h; Inert atmosphere;	80%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 8h; Inert atmosphere; Reflux;	68%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 8h; Inert atmosphere; Reflux;	68%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 95℃; for 15h; Suzuki-Miyaura Coupling;

1,2-Dichloro-3-nitrobenzene (3209-22-1) + Benzimidazol-2-thiol (134469-07-1) → 4-chlorobenzo[d]benzo[4,5]imidazo[2,1-b]thiazole (1403604-87-4)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 130℃; Inert atmosphere;	83%
With caesium carbonate In dimethyl sulfoxide at 130℃; for 2h;	58%

1,2-Dichloro-3-nitrobenzene (3209-22-1) + 2-Methoxyphenylboronic acid (5720-06-9) → C13H10ClNO3 (1057482-83-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; water; toluene for 12h; Inert atmosphere; Reflux;	83%
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In ethanol; water; toluene for 12h; Inert atmosphere; Reflux;	83%

Upstream product

• 151169-74-3 2,3-dichlorobenzeneboronic acid 
• 95-51-2 o-chloroaniline 
• 60956-27-6 N-(2,3-dinitrophenyl)acetamide 
• 122-28-1 N-(3-nitrophenyl)acetanilide 
• 121-73-3 3-Nitrochlorobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 10025-91-9 antimony(III) chloride 
• 7782-50-5 chlorine 
• 98-95-3 nitrobenzene 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 95-50-1 1,2-dichloro-benzene 
• 769-11-9 2-chloro-6-nitroaniline 
• 602-03-9 2,3-dinitroaniline 

Downstream Products

• 80866-77-9 1-chloro-2-methoxy-3-nitro-benzene 
• 65516-83-8 1-Chlor-2,3-bis(methylthio)benzol 
• 124-38-9 carbon dioxide 
• 1242283-75-5 C₁₄H₁₇Cl₂N₂O₅PS₂ 
• 1450819-41-6 4,5-dichloro-9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrimido[4,5-b]indole 
• 1034474-42-4 3-(3-bromo-5-chlorophenoxy)-4-chloro-2-nitroaniline 
• 1345336-62-0 C₁₂H₇BrCl₂N₂O₃ 
• 1034474-40-2 tert-butyl 3-{[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate 
• 1034474-21-9 3-chloro-5-{[5-chloro-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1H-1,2,3-benzotriazol-4-yl]oxy}benzonitrile 
• 1345336-78-8 3-chloro-5-[(5-chloro-2-methyl-1H-benzimidazol-4-yl)oxy]benzonitrile 
• 1345336-76-6 3-chloro-5-[(5-chloro-2-oxo-2,3-dihydro-1H-benzimidazol-4-yl)oxy]benzonitrile 
• 1034708-82-1 3-chloro-5-[(5-chloro-1H-benzimidazol-4-yl)oxy]benzonitrile 
• 1034474-39-9 3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile 
• 1345336-71-1 4-(3-bromo-5-chlorophenoxy)-5-chloro-2-methyl-1H-benzimidazole 

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