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2,4-Dichloronitrobenzene

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Name

2,4-Dichloronitrobenzene

EINECS 210-248-3
CAS No. 611-06-3 Density 1.533 g/cm3
PSA 45.82000 LogP 3.42480
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 Molecular Structure of 611-06-3 (2,4-Dichloronitrobenzene) Hazard Symbols IrritantXi, DangerousN, HarmfulXn
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;

Article Data 35

2,4-Dichloronitrobenzene Synthetic route

541-73-1

1,3-Dichlorobenzene

611-06-3

2,4-dichloronitrobenzene

Conditions
ConditionsYield
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 tetrachloromethane65.3%
2516-95-2

5-chloro-2-nitrobenzoic acid

611-06-3

2,4-dichloronitrobenzene

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With 3,3-dimethyldioxirane In acetone at 20℃;A 12%
B 36%
C 23%
5866-97-7

2,6-dichloro-3-nitrobenzaldehyde

611-06-3

2,4-dichloronitrobenzene

Conditions
ConditionsYield
With potassium hydroxide at 100℃;
13785-48-3

2,6-dichloro-3-nitroaniline

611-06-3

2,4-dichloronitrobenzene

Conditions
ConditionsYield
With ethyl nitrite; ethanol
342043-37-2

2-nitro-3,5-dichloroacetanilide

611-06-3

2,4-dichloronitrobenzene

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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.

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 C6H3Cl2NO2 and 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, ZrCl4 and 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

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