1,2-Dichloro-4-nitrobenzene

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1,2-Dichloro-4-nitrobenzene
1,2-Dichloro-4-nitrobenzene.png
Identifiers
CAS number 99-54-7 N
ChemSpider 21106095 YesY
ChEMBL CHEMBL167468 YesY
Jmol-3D images Image 1
Properties
Molecular formula C6H3Cl2NO2
Molar mass 192.01
Appearance yellow needles
Density 1.4588 g/cm3
Melting point 52.8-56 °C
Boiling point 263 °C
Solubility in water organic solvents
Except where noted otherwise, 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[edit]

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[edit]

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