1,2-Dichloro-4-nitrobenzene

1,2-Dichloro-4-nitrobenzene
Other names DCNB, 3,4-dichloronitrobenzene
Identifiers
CAS number	99-54-7 N
ChemSpider	21106095 Y
ChEMBL	CHEMBL167468 Y
Jmol-3D images	Image 1
SMILES Clc1ccc(cc1Cl)[N+]([O-])=O
InChI InChI=1S/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H Y Key: NTBYINQTYWZXLH-UHFFFAOYSA-N Y InChI=1/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H Key: NTBYINQTYWZXLH-UHFFFAOYAQ
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
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. ^ ^{a b} Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.