1,2-Dichloro-4-nitrobenzene

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.

1,2-Dichloro-4-nitrobenzene
Names
Preferred IUPAC name
1,2-Dichloro-4-nitrobenzene
Other names
DCNB, 3,4-dichloronitrobenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.513
EC Number
  • 202-764-2
RTECS number
  • CZ5250000
UNII
UN number 2811 1578
Properties
C6H3Cl2NO2
Molar mass 192.01
Appearance colourless to 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
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H302, H336, H361, H372, H373, H401, H411
P201, P202, P260, P261, P264, P270, P271, P273, P281, P301+312, P304+340, P308+313, P312, P314, P330, P391, P403+233, P405, P501
Flash point 124 °C (255 °F; 397 K)
420 °C (788 °F; 693 K)
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

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 1-chloro-4-nitrobenzene.[1]

One of the chlorides is reactive toward nucleophiles. Potassium fluoride gives 2-chloro-1-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.
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