1,2-Dichloro-4-nitrobenzene

1,2-Dichloro-4-nitrobenzene
Names
Other names
DCNB, 3,4-dichloronitrobenzene
Identifiers
99-54-7 N
ChEMBL ChEMBL167468 YesY
ChemSpider 21106095 YesY
Jmol interactive 3D Image
Properties
C6H3Cl2NO2
Molar mass 192.01
Appearance yellow needles
Density 1.4588 g/cm3
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)
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. 1 2 Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.
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