ChemicalBook CAS DataBase List 2,6-Dichloronitrobenzene

2,6-Dichloronitrobenzene synthesis

13synthesis methods

Product Name:2,6-Dichloronitrobenzene
CAS Number:601-88-7
Molecular formula:C6H3Cl2NO2
Molecular Weight:192

608-31-1

601-88-7

2.1.5. Synthesis of 1,3-dichloro-2-nitrobenzene[4]. 2,6-Dichloroaniline (8.10 g, 50.0 mmol) was dissolved in dichloromethane (200 mL) and the solution was cooled to 0 °C. A solution of 3-chloroperbenzoic acid (24.6 g, 100 mmol) in dichloromethane (250 mL) was slowly added dropwise at 0 °C for a controlled time of 1.5 hours. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 2 hours. Subsequently, the reaction mixture was diluted with dichloromethane (250 mL). The reaction mixture was washed sequentially with 2 wt% aqueous sodium thiosulfate (2 x 100 mL), aqueous sodium bicarbonate (4 x 50 mL) and deionized water (200 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure to remove the solvent. The residue was suspended in n-hexane (40 mL), sonicated for 5 min and filtered, and the filter cake was washed with n-hexane (2 x 20 mL) to afford 1,3-dichloro-2-nitrobenzene (6.63 g, 37.7 mmol, 75% yield) as a beige solid.

608-31-1 Synthesis

608-31-1
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601-88-7
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Yield:601-88-7 92%

Reaction Conditions:

Stage #1:2,6-Dichloroaniline with sodium tungstate (VI) dihydrate;sulfuric acid in methanol at 40;
Stage #2: with dihydrogen peroxide in methanol;water; pH=0.5 at 40; for 9 h;
Stage #3: with potassium hydroxide in methanol;water at 20 - 40; for 2 h;Reagent/catalyst;pH-value;Temperature;Solvent;

Steps:

1 Example 1 Production of 2,6-Dichloronitrobenzene
1.32 g (4.0 mmol) of sodium tungstate dihydrate and 4.0 g (40 mmol) of concentrated sulfuric acid were added to a solution of 16.2 g (100 mmol) of 2,6-dichloroaniline in 120 ml of methanol, and the mixture was heated to 40° C. 30 ml (291 mmol) of a 30% hydrogen peroxide solution was added dropwise over 10 hours.
The pH value at this time was 0.5.
After the completion of the dropwise addition, the mixture was stirred at 40° C. for 9 hours.
After the disappearance of the 2,6-dichloroaniline was confirmed by gas chromatography (area percentage method), a solution of 9.8 g (150 mmol) of 86% potassium hydroxide in 24.3 ml of methanol was added dropwise while the temperature of the reaction liquid was adjusted to 40° C. or less.
After the completion of the dropwise addition, the mixture was stirred at room temperature for 2 hours, and the reaction was completed.
After the completion of the reaction, 95 ml of toluene and 32 ml of water were added, and the mixture was stirred for a while, and filtered.
The filtrate was separated.
The obtained organic phase was washed with 8 ml of water, and then heated to reflux, and dehydrated.
Thus, 2,6-dichloronitrobenzene was obtained as a toluene solution.
This solution was analyzed by gas chromatography by the absolute calibration method, and as a result, the yield was 92%.

References:

IHARA CHEMICAL INDUSTRY CO., LTD.;Tani, Shinki;Yadomatsu, Nami;Ikumi, Akiko;Hirano, Yuuki;Ido, Takuya US2014/163256, 2014, A1 Location in patent:Paragraph 0161-0162

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541-73-1 Synthesis