1,2-Dichloro-4-nitrobenzene

1,2-Dichloro-4-nitrobenzene

Names
Other names DCNB, 3,4-dichloronitrobenzene
Identifiers
CAS Number	99-54-7
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL167468
ChemSpider	21106095
ECHA InfoCard	100.002.513
InChI InChI=1S/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H Key: NTBYINQTYWZXLH-UHFFFAOYSA-N InChI=1/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H Key: NTBYINQTYWZXLH-UHFFFAOYAQ
SMILES Clc1ccc(cc1Cl)[N+]([O-])=O
Properties
Chemical formula	C6H3Cl2NO2
Molar mass	192.01
Appearance	yellow needles
Density	1.4588 g/cm^3
Melting point	52.8 to 56 °C (127.0 to 132.8 °F; 325.9 to 329.1 K)
Boiling point	263 °C (505 °F; 536 K)
Solubility in water	organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,2-Dichloro-4-nitrobenzene is an organic compound with the formula 1,2-Cl₂C₆H₃-4-NO₂. This pale yellow solid is related to 1,2-dichlorobenzene by the replacement of one H atom with a nitro functional group. This compound is an intermediate in the synthesis of agrochemicals.

Production and uses

The nitration of 1,2-dichlorobenzene mainly produces 1,2-dichloro-4-nitrobenzene, together with smaller amounts of the 3-nitro isomer. It can also be prepared by chlorination of 4-chloronitrobenzene.^[1]

One of the chlorides is reactive toward nucleophiles. Potassium fluoride gives 1-chloro-2-fluoro-4-nitrobenzene, an intermediate in the production of herbicides. With ammonia, one obtains 2-chloro-4-nitroaniline, a precursor to diazo dyes. Reduction with iron powder gives 3,4-dichloroaniline (m.p. 72 °C, CAS# 95-76-1).^[1]

References

1. Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.