1,4-Dichloro-2-nitrobenzene

1,4-Dichloro-2-nitrobenzene is an organic compound with the formula C6H3Cl2NO2. One of several isomers of dichloronitrobenzene, it is a yellow solid that is insoluble in water. It is produced by nitration of 1,4-dichlorobenzene. It is a precursor to many derivatives of commercial interest. Hydrogenation gives 1,4-dichloroaniline. Nucleophiles displace the chloride adjacent to the nitro group: ammonia gives the aniline derivative, aqueous base gives the phenol derivative, and methoxide gives the anisole derivative. These compounds are respectively 4-chloro-2-nitroaniline, 4-chloro-2-nitrophenol, and 4-chloro-2-nitroanisole.[2]

1,4-Dichloro-2-nitrobenzene
Names
Preferred IUPAC name
1,4-Dichloro-2-nitrobenzene
Other names
Nitro-P-dichlorobenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.749
MeSH C503932
RTECS number
  • CZ5260000
UNII
UN number 1578
  • InChI=1S/C6H3Cl2NO2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H
    Key: RZKKOBGFCAHLCZ-UHFFFAOYSA-N
  • c1cc(c(cc1Cl)[N+](=O)[O-])Cl
Properties
C6H3Cl2NO2
Molar mass 192.00
Appearance yellow flakes
Density 1.67
Melting point 52–54 °C (126–129 °F; 325–327 K)
Boiling point 266–269 °C (511–516 °F; 539–542 K)
95 mg/L
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H336, H351, H361, H370, H372, H373, H410
P201, P202, P260, P261, P264, P270, P271, P273, P281, P301+P312, P304+P340, P307+P311, P308+P313, P312, P314, P321, P330, P391, P403+P233, P405, P501
Flash point 135 °C (275 °F; 408 K)
465 °C (869 °F; 738 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Disperse Yellow 42, a popular dye for polyesters, is derived from 1,4-dichloro-2-nitrobenzene.[1]

References
  1. Raue, Roderich; Corbett, John F. (2000). "Nitro and Nitroso Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_383.
  2. Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.
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