601-88-7

Basic information

• Product Name: 2,6-Dichloronitrobenzene
• Synonyms: Benzene, 1,3-dichloro-2-nitro-;2,6-Dichloronitrobenezene;1,3-DICHLORO-3-NITROBENZENE;1,3-Dichloro-2-nitrobenzene;2,6-Dichloronitrobenzene;1-Nitro-2,6-dichlorobenzene
• CAS NO: 601-88-7
• Molecular Formula: C₆H₃Cl₂NO₂
• Molecular Weight: 192
• EINECS: 210-009-3
• Product Categories: Benzene derivates
• Mol File: 601-88-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 71 °C
• Boiling Point: 130 °C / 8mmHg
• Flash Point: 118.9 °C
• Appearance: Powder, alcohol-resistant foam, water spray, carbon dioxide.
• Density: 1.6030
• Vapor Pressure: 0.00987mmHg at 25°C
• Refractive Index: 1.5929 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2,6-Dichloronitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichloronitrobenzene(601-88-7)
• EPA Substance Registry System: 2,6-Dichloronitrobenzene(601-88-7)

Safety Data

• Hazard Codes: T
• RIDADR: 1578
• Hazardous Substances Data: 601-88-7(Hazardous Substances Data)

Usage

Uses

1,3-Dichloro-2-nitrobenzene is an olfactory mucosa (OM) toxicants.Also, it is a starting material for 9-Chloro Quetiapine (C366040), which is an impurity of Quetiapine hemifumarate (Q510000), a dibenzothiazepine antipsychotic medication used in the treatment of schizophrenia.

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

Synthetic route

2,6-Dichloroaniline (608-31-1) → 2,6-dichloronitrobenzene (601-88-7)

Conditions	Yield
Stage #1: 2,6-Dichloroaniline With sodium tungstate (VI) dihydrate; sulfuric acid In methanol at 40℃; Stage #2: With dihydrogen peroxide In methanol; water at 40℃; for 9h; pH=0.5; Stage #3: With potassium hydroxide In methanol; water at 20 - 40℃; for 2h; Reagent/catalyst; pH-value; Temperature; Solvent;	92%
With sodium perborate In acetic acid at 50 - 55℃;	87%
With sodium perborate In acetic acid at 50 - 60℃; for 2h;	87%

(2,6-dichlorophenyl)(phenyl)iodonium triflate → 2,6-dichloronitrobenzene (601-88-7)

Conditions	Yield
With sodium nitrite In ethyl acetate at 70℃; for 16h; Temperature; Solvent; Sealed tube; chemoselective reaction;	91%

2,6-dichloro-4-aminonitrobenzene (59992-52-8) → 2,6-dichloronitrobenzene (601-88-7)

2,4-dichloro-3-nitroaniline (129825-24-7) → 2,6-dichloronitrobenzene (601-88-7)

acetic acid-(3,5-dichloro-4-nitro-anilide) (5942-05-2) → 2,6-dichloronitrobenzene (601-88-7)

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

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;

2,6-dichloronitrosobenzene (1194-66-7) → 2,6-dichloronitrobenzene (601-88-7)

Conditions	Yield
With nitric acid Heating;

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

N-(3,5-dichlorophenyl)-acetamide (31592-84-4) → 2,6-dichloronitrobenzene (601-88-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / die Acetanilide trennt man mit CS2 zersetzt man durch Erhitzen mit konz.Schwefelsaeure View Scheme
Multi-step reaction with 2 steps 1: Nitrieren; mann trennt das Gemenge durch CS2, worin sich nur 3.5-Dichlor-2-nitro-acetanilid loest, und verseift durch Erhitzen mit konz.Schwefelsaeure View Scheme

3-nitro-aniline (99-09-2) → 2,6-dichloronitrobenzene (601-88-7)

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

diclofenac sodium (15307-79-6) → 2-oxoindole (59-48-3) + 2,6-Dichlorophenol (87-65-0) + 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 4-chloro-10(H)acridin-9-one (69220-40-2) + 2,6-dichloronitrobenzene (601-88-7) + N-phenyl-2,6-dichloroaniline (15307-93-4) + N-(2,6-dichlorophenyl)-formamide (10113-35-6) + 1,3-dichloro-2-isocyanobenzene (6697-95-6) + 2,6-dichlorophenylisocyanate (39920-37-1) + 4-chloro-1,3-benzoxazol-2(3H)-one (13603-93-5) + 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With dihydrogen peroxide; iron(II) In water at 20℃; pH=2; Fenton Reaction;

...Expand

1,3-dichloro-2-iodobenzene (19230-28-5) → 2,6-dichloronitrobenzene (601-88-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C / Sealed tube 2: sodium nitrite / ethyl acetate / 16 h / 70 °C / Sealed tube 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;

2,6-dichloronitrobenzene (601-88-7) → 1-chloro-2,4-dinitrochlorobenzene (10199-85-6)

Conditions	Yield
With sulfuric acid; sulfur trioxide; nitric acid In acetic acid at 25℃; Rate constant; variation of HNO3 and H2SO4 concentration;	100%
durch Nitrierung;
With nitric acid

piperidine (110-89-4) + 2,6-dichloronitrobenzene (601-88-7) → 2,6-di-piperidin-1-yl-nitrobenzene (1172626-77-5)

Conditions	Yield
for 216h; Neat (no solvent); Reflux;	99.5%

pyrrolidine (123-75-1) + 2,6-dichloronitrobenzene (601-88-7) → 2,6-dipyrrolidin-1-yl-nitrobenzene (1172626-76-4)

Conditions	Yield
at 118℃; for 120h; Neat (no solvent);	97%

2,6-dichloronitrobenzene (601-88-7) → 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With ammonium formate at 20℃; for 0.75h; Reduction;	91%
With hydrogenchloride; tin
With hydrogen; silver; silica gel In ethanol at 140℃; under 15001.2 Torr; for 3h;	100 % Chromat.

2,6-dichloronitrobenzene (601-88-7) + 2-anilineboronic acid pinacol ester (191171-55-8) → C12H9ClN2O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; Inert atmosphere;	90%

2,6-dichloronitrobenzene (601-88-7) + 3-chloro-aniline (108-42-9) → 3-chloro-N-(3-chlorophenyl)-2-nitroaniline

Conditions	Yield
Stage #1: 3-chloro-aniline With sodium hydride In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: 2,6-dichloronitrobenzene In tetrahydrofuran at 10 - 15℃;	89%
With sodium acetate; nitrobenzene

2,6-dichloronitrobenzene (601-88-7) + phenylboronic acid (98-80-6) → 3-chloro-2-nitrobiphenyl (82341-97-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 12h; Reflux; Inert atmosphere;	89%

2,6-dichloronitrobenzene (601-88-7) + 4-chloro-aniline (106-47-8) → 3-chloro-N-(4-chlorophenyl)-2-nitroaniline

Conditions	Yield
Stage #1: 4-chloro-aniline With sodium hydride In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: 2,6-dichloronitrobenzene In tetrahydrofuran at 10 - 15℃;	87%
With sodium acetate; nitrobenzene

2,6-dichloronitrobenzene (601-88-7) + chloroformic acid ethyl ester (541-41-3) → (2,6-dichloro-phenyl)-carbamic acid ethyl ester

Conditions	Yield
With tin; ammonium chloride In methanol at 25℃; for 3h; Sonication;	87%

2,6-dichloronitrobenzene (601-88-7) + 2-Chloroaniline (95-51-2) → 3-chloro-N-(2-chlorophenyl)-2-nitroaniline

Conditions	Yield
Stage #1: o-chloroaniline With sodium hydride In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: 2,6-dichloronitrobenzene In tetrahydrofuran at 10 - 15℃;	85%
With sodium acetate; nitrobenzene

di-tert-butyl dicarbonate (24424-99-5) + 2,6-dichloronitrobenzene (601-88-7) → tert-butyl (2,6-dichlorophenyl)carbamate (56700-68-6)

Conditions	Yield
With tin; ammonium chloride In methanol at 25℃; for 5h; Sonication;	85%

morpholine (110-91-8) + 2,6-dichloronitrobenzene (601-88-7) → 2,6-di-morpholin-4-yl-nitrobenzene (179900-23-3)

Conditions	Yield
for 216h; Neat (no solvent); Reflux;	84.5%

2,6-dichloronitrobenzene (601-88-7) → 4-chloro-2,1,3-benzoxadiazole (7116-16-7)

Conditions	Yield
With sodium azide In dimethyl sulfoxide at 20 - 120℃; for 3.08h;	81%

2,6-dichloronitrobenzene (601-88-7) + thiophenol (108-98-5) → (2-nitro-1,3-phenylene)bis(phenylsulfane) (98119-89-2)

Conditions	Yield
Stage #1: thiophenol With sodium In ethanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,6-dichloronitrobenzene In ethanol for 21h; Inert atmosphere; Reflux;	77%

2,6-dichloronitrobenzene (601-88-7) + m-Anisidine (536-90-3) → 3-chloro-N-(3-methoxyphenyl)-2-nitroaniline

Conditions	Yield
Stage #1: m-Anisidine With sodium hydride In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: 2,6-dichloronitrobenzene In tetrahydrofuran at 10 - 15℃;	77%

2,6-dichloronitrobenzene (601-88-7) + 2-methoxy-phenylamine (90-04-0) → 3-chloro-N-(2-methoxyphenyl)-2-nitroaniline

Conditions	Yield
Stage #1: 2-methoxy-phenylamine With sodium hydride In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: 2,6-dichloronitrobenzene In tetrahydrofuran at 10 - 15℃;	77%

2,6-dichloronitrobenzene (601-88-7) + 3-chloro-4-methoxyaniline (5345-54-0) → 3-chloro-N-(3-chloro-4-methoxyphenyl)-2-nitroaniline

Conditions	Yield
Stage #1: 3-chloro-4-methoxyaniline With sodium hydride In tetrahydrofuran at 70℃; Inert atmosphere; Stage #2: 2,6-dichloronitrobenzene In tetrahydrofuran at 10 - 15℃;	77%

2,6-diisopropylbenzenamine (24544-04-5) + 2,6-dichloronitrobenzene (601-88-7) → C18H21ClN2O2 (1172626-81-1) + 2,6-bis(2,6-diisopropylanilino)nitrobenzene (1172626-79-7)

Conditions	Yield
With palladium diacetate; caesium carbonate; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In toluene at 100℃; for 48h; Inert atmosphere;	A 6% B 74%

2,6-dichloronitrobenzene (601-88-7) + 2,4,6-trimethylaniline (88-05-1) → C15H15ClN2O2 (1172626-82-2) + 2,6-bis(2,4,6-trimethylanilino)nitrobenzene (1172626-80-0)

Conditions	Yield
With palladium diacetate; caesium carbonate; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In toluene at 100℃; for 48h; Inert atmosphere;	A 17% B 74%

2,6-dichloronitrobenzene (601-88-7) + aniline (62-53-3) → 2-nitro-N1,N3-diphenylbenzene-1,3-diamine (1172626-78-6) + (3-chloro-2-nitro-phenyl)-phenyl-amine

Conditions	Yield
With palladium diacetate; caesium carbonate; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In toluene at 100℃; for 48h; Inert atmosphere;	A 72.9% B 14%

2-bromothiophenol (6320-02-1) + 2,6-dichloronitrobenzene (601-88-7) → 1,3-Bis-(2-bromo-phenylsulfanyl)-2-nitro-benzene (790277-57-5)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 90℃; for 2h;	72%

2,6-dichloronitrobenzene (601-88-7) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-[4-(3-chloro-2-nitroanilino)phenyl]ethanol

Conditions	Yield
With sodium acetate at 160℃; for 3h; in a sealed tube;	72%

2,6-dichloronitrobenzene (601-88-7) + aniline (62-53-3) → 2-nitro-N1,N3-diphenylbenzene-1,3-diamine (1172626-78-6)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate for 8h; Inert atmosphere; Reflux;	72%

2,6-dichloronitrobenzene (601-88-7) + phenol (108-95-2) → 1-chloro-2-nitro-3-phenoxybenzene (104272-69-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 6h; Heating;	71.8%

4-dibenzofurylboronic acid (100124-06-9) + 2,6-dichloronitrobenzene (601-88-7) → C18H10ClNO3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water; toluene for 12h; Inert atmosphere; Reflux;	71%

2,6-dichloronitrobenzene (601-88-7) → 1-bromo-2,4-dichloro-3-nitrobenzene

Conditions	Yield
With N-Bromosuccinimide; sulfuric acid at 60℃; for 16h; Inert atmosphere;	70%

2,6-dichloronitrobenzene (601-88-7) + 2-Naphthalenethiol (91-60-1) → 2,6-bis(2-naphthylsulfanyl)nitrobenzene

Conditions	Yield
Stage #1: 2-Naphthalenethiol With sodium In ethanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,6-dichloronitrobenzene In ethanol for 4h; Inert atmosphere; Reflux;	69%

2,6-dichloronitrobenzene (601-88-7) → N-(2,6-dichlorophenyl)hydroxylamine (32847-25-9)

Conditions	Yield
With ammonium chloride; zinc In ethanol; water for 0.333333h; from 20 deg C to 40 deg C;	68%
In isopropyl alcohol Irradiation;

Upstream product

• 5942-05-2 acetic acid-(3,5-dichloro-4-nitro-anilide) 
• 608-31-1 2,6-Dichloroaniline 
• 121-73-3 3-Nitrochlorobenzene 
• 541-73-1 1,3-Dichlorobenzene 
• 19230-28-5 1,3-dichloro-2-iodobenzene 
• 15307-79-6 diclofenac sodium 
• 99-09-2 3-nitro-aniline 
• 31592-84-4 N-(3,5-dichlorophenyl)-acetamide 
• 7697-37-2 nitric acid 
• 1194-66-7 2,6-dichloronitrosobenzene 
• 129825-24-7 2,4-dichloro-3-nitroaniline 
• 59992-52-8 2,6-dichloro-4-aminonitrobenzene 

Downstream Products

• 103-19-5 di(p-tolyl) disulfide 
• 860240-96-6 (3-chloro-2-nitro-phenyl)-p-tolyl sulfide 
• 750633-82-0 2-nitro-1,3-bis-p-tolylsulfanyl-benzene 
• 790277-55-3 1,3-Bis-(2-bromo-phenoxy)-2-nitro-benzene 
• 1105738-90-6 3,5-dichloro-4-nitrobenzyl phenyl sulfone 
• 69709-39-3 4-methoxy-1-nitro-2-[(phenylsulfonyl)methyl]benzene 
• 1360624-09-4 (3-amino-2,4-dichloro-benzyl)-carbamic acid tert-butyl ester 
• 1360623-97-7 3-amino-2,4-dichloro-benzylamine 
• 943830-82-8 3-Bromo-2,6-dichloroaniline 
• 1172626-78-6 2,6-dianilinonitrobenzene 

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