2,6-Dichloronitrobenzene Chemical Properties

Melting point:

71 °C

Boiling point:

130 °C / 8mmHg

Density 

1.6030

refractive index 

1.5929 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

Pale Yellow to Pale Green

CAS DataBase Reference

601-88-7(CAS DataBase Reference)

NIST Chemistry Reference

1,3-dichloro-2-nitrobenzene(601-88-7)

Safety Information

Hazard Codes 

T

RIDADR 

1578

HS Code 

2904990090

2,6-Dichloronitrobenzene Usage And Synthesis

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.

Synthesis

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.

References

[1] Patent: US2014/163256, 2014, A1. Location in patent: Paragraph 0161-0162
[2] Tetrahedron Letters, 1983, vol. 24, # 14, p. 1505 - 1508
[3] Tetrahedron, 1987, vol. 43, # 8, p. 1753 - 1758
[4] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 768 - 778
[5] Journal of Medicinal Chemistry, 1968, vol. 11, # 4, p. 814 - 819

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