2,4-Dichloronitrobenzene supplier

Name
2,4-Dichloronitrobenzene
EINECS 210-248-3
CAS No. 611-06-3
Article Data35
CAS DataBase
Density 1.533 g/cm³
Solubility 188 mg/L (20 °C) in water
Melting Point 29-32 °C(lit.)
Formula C₆H₃Cl₂NO₂
Boiling Point 258.5 °C at 760 mmHg
Molecular Weight 192.001
Flash Point 116.9 °C
Transport Information UN 2811
Appearance Light yellow needles or amber crystalline solid
Safety 26-36-61-36/37-24
Risk Codes 36/37/38-51/53-43-21/22
Molecular Structure
Hazard Symbols Xi, N, Xn
Synonyms 1,3-Dichloro-4-nitrobenzene;2,4-dichloro-1-nitrobenzene;2,4-dichloro-1-nitro-benzene;1, 3-Dichloro-4-nitrobenzene;Benzene, 2,4-dichloro-1-nitro-;2,4-Dichloro Nitrobenzene;
PSA 45.82000
LogP 3.42480

Synthetic route

: 541-73-1
1,3-Dichlorobenzene

: 611-06-3
2,4-dichloronitrobenzene

Conditions

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%

: 2516-95-2
5-chloro-2-nitrobenzoic acid

: 611-06-3
2,4-dichloronitrobenzene

Conditions

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%

: 68716-47-2
2,4-dichlorophenylboronic acid

: 611-06-3
2,4-dichloronitrobenzene

Conditions

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

: 554-00-7
2,4-Dichloroaniline

: 611-06-3
2,4-dichloronitrobenzene

Conditions

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

: 142-04-1
aniline hydrochloride

A: 611-06-3
2,4-dichloronitrobenzene

B: 100-00-5
4-chlorobenzonitrile

C: 88-73-3
2-Chloronitrobenzene

Conditions

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

...Expand

: 5866-97-7
2,6-dichloro-3-nitrobenzaldehyde

: 611-06-3
2,4-dichloronitrobenzene

Conditions

Conditions	Yield
With potassium hydroxide at 100℃;

: 13785-48-3
2,6-dichloro-3-nitroaniline

: 611-06-3
2,4-dichloronitrobenzene

Conditions

Conditions	Yield
With ethyl nitrite; ethanol

: 342043-37-2
2-nitro-3,5-dichloroacetanilide

: 611-06-3
2,4-dichloronitrobenzene

Conditions

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

: 88-73-3
2-Chloronitrobenzene

A: 611-06-3
2,4-dichloronitrobenzene

B: 3209-22-1
1,2-Dichloro-3-nitrobenzene

Conditions

Conditions	Yield
With antimonypentachloride beim Chlorieren;

: 98-95-3
nitrobenzene

A: 611-06-3
2,4-dichloronitrobenzene

B: 121-73-3
3-Chloronitrobenzene

C: 82-68-8
Quintozene

D: 88-73-3
2-Chloronitrobenzene

Conditions

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.

...Expand

: 541-73-1
1,3-Dichlorobenzene

A: 611-06-3
2,4-dichloronitrobenzene

B: 618-62-2
3,5-dichloro-1-nitrobenzene

C: 601-88-7
2,6-dichloronitrobenzene

Conditions

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;

...Expand

: 1635-61-6
5-chloro-2-nitroaniline

: 611-06-3
2,4-dichloronitrobenzene

Conditions

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

: 7647-18-9
antimonypentachloride

: 88-73-3
2-Chloronitrobenzene

A: 611-06-3
2,4-dichloronitrobenzene

B: 89-61-2
2,5-dichloronitrobenzene

C 2.3-dichloro-1-nitrobenzene: 2.3-dichloro-1-nitrobenzene

Conditions

Conditions	Yield
at 100℃; durch Chlorierung;

...Expand

: 7697-37-2
nitric acid

: 541-73-1
1,3-Dichlorobenzene

: 611-06-3
2,4-dichloronitrobenzene

: 7697-37-2
nitric acid

: 541-73-1
1,3-Dichlorobenzene

A: 611-06-3
2,4-dichloronitrobenzene

B: 601-88-7
2,6-dichloronitrobenzene

...Expand

: 5866-97-7
2,6-dichloro-3-nitrobenzaldehyde

aqueous KOH-solution: aqueous KOH-solution

A: 64-18-6
formic acid

B: 611-06-3
2,4-dichloronitrobenzene

...Expand

diazotized 2-nitro-5-chloro-aniline: diazotized 2-nitro-5-chloro-aniline

A: 611-06-3
2,4-dichloronitrobenzene

B: 19036-42-1
5,5'-dichloro-2,2'-dinitro-1,1'-biphenyl

Conditions

Conditions	Yield
With hydrogenchloride; copper dichloride

: 99-09-2
3-nitro-aniline

: 611-06-3
2,4-dichloronitrobenzene

Conditions

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

: 121-73-3
3-Chloronitrobenzene

A: 611-06-3
2,4-dichloronitrobenzene

B: 601-88-7
2,6-dichloronitrobenzene

Conditions

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

: 541-73-1
1,3-Dichlorobenzene

A: 611-06-3
2,4-dichloronitrobenzene

B: 601-88-7
2,6-dichloronitrobenzene

Conditions

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

: C8H8ClNO3

: 611-06-3
2,4-dichloronitrobenzene

Conditions

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.

: 18640-60-3
5-chloro-2-nitroacetophenone

: 611-06-3
2,4-dichloronitrobenzene

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 446-35-5
2,4-Difluoronitrobenzene

Conditions

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%

: 611-06-3
2,4-dichloronitrobenzene

: 74-89-5
methylamine

: 35966-84-8
4-chloro-2-methylaminonitrobenzene

Conditions

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%

: 611-06-3
2,4-dichloronitrobenzene

: 554-00-7
2,4-Dichloroaniline

Conditions

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%

: 611-06-3
2,4-dichloronitrobenzene

: 109-55-7
1-amino-3-(dimethylamino)propane

: 92547-10-9
N1-(5-chloro-2-nitrophenyl)-N3,N3-dimethylpropane-1,3-diamine

Conditions

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%

: 611-06-3
2,4-dichloronitrobenzene

: 120-83-2
2,4-dichlorophenol

: 57532-59-9
2,4-bis(2,4-dichlorophenoxy)-nitrobenzene

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 89-69-0
2,4,5-Trichloronitrobenzene

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 106-54-7
p-Chlorothiophenol

: 2,4-bis[(4-chlorophenyl)thio]-1-nitrobenzene

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 141-43-5
ethanolamine

: 50610-29-2
2-<(5-chloro-2-nitro)phenylamino>ethanol

Conditions

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%

: 611-06-3
2,4-dichloronitrobenzene

: 2183-66-6
4-amino-2-(methylthio)pyrimidine

: 1429658-37-6
C11H9ClN4O2S

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 105-56-6
ethyl 2-cyanoacetate

: 62567-91-3
ethyl 2-(5-chloro-2-nitrophenyl)-2-cyanoacetate

Conditions

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;

: 611-06-3
2,4-dichloronitrobenzene

: 789-24-2
9-Phenylfluorene

: 124233-18-7
9-(3-chloro-4-nitrophenyl)-9-phenylfluorene

Conditions

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

: 626-67-5
N-methylcyclohexylamine

: 611-06-3
2,4-dichloronitrobenzene

: 2-chloro-4-piperidinonitrobenzene

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 108-98-5
thiophenol

: 2-chloro-4-phenylthio nitrobenzene

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 108-59-8
malonic acid dimethyl ester

: 582305-49-5
2-(4-chloro-2-nitro-phenyl)-malonic acid dimethyl ester

Conditions

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%

: 611-06-3
2,4-dichloronitrobenzene

: 13557-25-0
1-(1-chloroethyl)phenyl sulfone

: 117508-91-5
1-(3,5-dichloro-2-nitrophenyl)ethyl phenyl sulphone

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 109-89-7
diethylamine

A: 133387-29-8
N,N-diethyl-5-chloro-2-nitro-aniline

B: 133387-32-3
N1,N1,N3,N3-Tetraethyl-4-nitro-benzene-1,3-diamine

Conditions

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

...Expand

: 123-75-1
pyrrolidine

: 611-06-3
2,4-dichloronitrobenzene

: 133387-30-1
4-chloro-2-(1-pyrrolidinyl)nitrobenzene

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 108-98-5
thiophenol

: 43156-47-4
2-nitro-5-phenylthioaniline

Conditions

Conditions	Yield
With ammonia In isopropyl alcohol	89.5%

: 123-75-1
pyrrolidine

: 611-06-3
2,4-dichloronitrobenzene

A: 133387-31-2
2-chloro-4-(1-pyrrolidinyl)nitrobenzene

B: 133387-30-1
4-chloro-2-(1-pyrrolidinyl)nitrobenzene

C: 133387-33-4
2,4-di(1-pyrrolidinyl)nitrobenzene

Conditions

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

...Expand

: 611-06-3
2,4-dichloronitrobenzene

: 149-30-4
2-Mercaptobenzothiazole

: 2-(3-Chloro-4-nitro-phenylsulfanyl)-benzothiazole

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 106-54-7
p-Chlorothiophenol

: 105945-59-3
4-chloro-2-(4-chlorophenylthio)nitrobenzene

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 111-86-4
n-Octylamine

: 1156057-44-1
N-octyl-2-nitro-5-chloroaniline

Conditions

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

: 611-06-3
2,4-dichloronitrobenzene

: 62-53-3
aniline

Conditions

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

: 110-91-8
morpholine

: 611-06-3
2,4-dichloronitrobenzene

A: 65976-65-0
4-(3-chloro-4-nitrophenyl)morpholine

B: 65976-63-8
4-(5-chloro-2-nitrophenyl)morpholine

C: 133387-34-5
4-[3-(morpholin-4-yl)-4-nitrophenyl]morpholine

Conditions

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

...Expand

: 611-06-3
2,4-dichloronitrobenzene

: 17348-69-5
5-chlorobenzofurazan-1-oxide

Conditions

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

: 91-21-4
1,2,3,4-tetrahydroisoquinoline

: 611-06-3
2,4-dichloronitrobenzene

: 9-chloro-5,6-dihydrobenzo[4,5]imidazo[2,1-a]isoquinoline

Conditions

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

: 696-59-3
cis,trans-2,5-dimethoxytetrahydrofuran

: 611-06-3
2,4-dichloronitrobenzene

: 383137-35-7
1-(2,4-dichlorophenyl)-1H-pyrrole

Conditions

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%

: 611-06-3
2,4-dichloronitrobenzene

: 124-41-4
sodium methylate

: 28987-59-9
3-chloro-4-nitroanisole

Conditions

Conditions	Yield
In methanol at 68℃;	85.5%

2,4-Dichloronitrobenzene Specification

The CAS register number of 2,4-Dichloronitrobenzene is 611-06-3. It also can be called as 1,3-Dichloro-4-nitrobenzene and the IUPAC name about this chemical is 2,4-dichloro-1-nitrobenzene. The molecular formula about this chemical is C₆H₃Cl₂NO₂and the molecular weight is 192.00. It belongs to the following product categories, such as Chlorobenzene Series; Benzene derivates and so on. This chemical is not compatible with strong oxidizing agents, strong bases, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide.

Physical properties about 2,4-Dichloronitrobenzene are: (1)ACD/LogP: 3.00; (2)ACD/LogD (pH 5.5): 3; (3)ACD/LogD (pH 7.4): 3; (4)ACD/BCF (pH 5.5): 112; (5)ACD/BCF (pH 7.4): 112; (6)ACD/KOC (pH 5.5): 1019.66; (7)ACD/KOC (pH 7.4): 1019.66; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 45.82Å²; (11)Index of Refraction: 1.595; (12)Molar Refractivity: 42.58 cm³; (13)Molar Volume: 125.1 cm³; (14)Polarizability: 16.88x10^-24cm³; (15)Surface Tension: 50.9 dyne/cm; (16)Enthalpy of Vaporization: 47.61 kJ/mol; (17)Boiling Point: 258.5 °C at 760 mmHg; (18)Vapour Pressure: 0.0221 mmHg at 25°C.

Preparation: this chemical can be prepared by aniline; hydrochloride, this reaction can also produce 1-chloro-4-nitro-benzene and 1-chloro-2-nitro-benzene. This reaction will need reagent dimethyldioxirane and solvent acetone. The reaction temperature is 20 ℃. The yield is about 12%.

Uses of 2,4-Dichloronitrobenzene: it can be used to produce 2,4-dichloro-aniline at heating. This reaction is a kind of Reduction. It will need reagent NaBH₄, ZrCl₄and solvent tetrahydrofuran with reaction time of 7 hours. The yield is about 84%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin and it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment, it is harmful in contact with skin and if swallowed, it may cause sensitization by skin contact. When you are using it, wear suitable protective clothing and gloves, you need avoid contact with skin and avoid release to the environment. Refer to special instructions / safety data sheets. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC(=C(C=C1Cl)Cl)[N+](=O)[O-]
(2)InChI: InChI=1S/C6H3Cl2NO2/c7-4-1-2-6(9(10)11)5(8)3-4/h1-3H
(3)InChIKey: QUIMTLZDMCNYGY-UHFFFAOYSA-N

Product Name

2,4-Dichloronitrobenzene

Synthetic route

2,4-Dichloronitrobenzene Specification

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