1,2-Dichloro-4-nitrobenzene

From Self-sufficiency
Jump to: navigation, search
1,2-Dichloro-4-nitrobenzene
File:1,2-Dichloro-4-nitrobenzene.png
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 99-54-7
ChemSpider 21106095
SMILES Script error: No such module "collapsible list".
InChI Script error: No such module "collapsible list".
InChI key NTBYINQTYWZXLH-UHFFFAOYAQ
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula C6H3Cl2NO2
Molar mass 192.01
Appearance yellow needles
Density 1.4588 g/cm3
Melting point

43 °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, 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. 1.0 1.1 Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.
nl:1,2-dichloor-4-nitrobenzeen

pt:1,2-Dicloro-4-nitrobenzeno