1,4-Dichloro-2-nitrobenzene

1,4-Dichloro-2-nitrobenzene
Names
	Preferred IUPAC name 1,4-Dichloro-2-nitrobenzene
	Other names Nitro-P-dichlorobenzene
Identifiers
CAS Number	89-61-2;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL354761;
ChemSpider	21111865;
ECHA InfoCard	100.001.749
MeSH	C503932
PubChem CID	6977;
RTECS number	CZ5260000;
UNII	IY18G50FF4;
UN number	1578
CompTox Dashboard (EPA)	DTXSID7052602 ;
	InChI InChI=1S/C6H3Cl2NO2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H Key: RZKKOBGFCAHLCZ-UHFFFAOYSA-N;
	SMILES c1cc(c(cc1Cl)[N+](=O)[O-])Cl;
Properties
Chemical formula	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)
Solubility in water	95 mg/L
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H336, H351, H361, H370, H372, H373, H410
Precautionary statements	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)
Autoignition; temperature	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

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]

Disperse Yellow 42, a popular dye for polyesters, is derived from 1,4-dichloro-2-nitrobenzene.^[1]

References

^ 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. ISBN 3527306730.
^ Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.

[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. ISBN 3527306730.

[Booth-2] Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.

[2]

[1]