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
  • InChI=1S/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H checkY
    Key: NTBYINQTYWZXLH-UHFFFAOYSA-N checkY
  • InChI=1/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H
    Key: NTBYINQTYWZXLH-UHFFFAOYAQ
  • Clc1ccc(cc1Cl)[N+]([O-])=O
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 labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H336, H361, H372, H373, H411
P201, P202, P260, P261, P264, P270, P271, P273, P281, P301+P312, P304+P340, P308+P313, P312, P314, P330, P391, P403+P233, 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).
☒N verify (what is checkY☒N ?)
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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