1,2-Dichloro-4-nitrobenzene

1,2-Dichloro-4-nitrobenzene
Names
	Preferred IUPAC name 1,2-Dichloro-4-nitrobenzene
	Other names DCNB, 3,4-dichloronitrobenzene
Identifiers
CAS Number	99-54-7 [chemspider];
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL167468 ;
ChemSpider	21106095 ;
ECHA InfoCard	100.002.513
EC Number	202-764-2;
PubChem CID	7443;
RTECS number	CZ5250000;
UNII	IJT74JI7FS;
UN number	2811 1578
CompTox Dashboard (EPA)	DTXSID8024999 ;
	InChI InChI=1S/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H Key: NTBYINQTYWZXLH-UHFFFAOYSA-N ; InChI=1/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H Key: NTBYINQTYWZXLH-UHFFFAOYAQ;
	SMILES Clc1ccc(cc1Cl)[N+]([O-])=O;
Properties
Chemical formula	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)
Solubility in water	organic solvents
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H336, H361, H372, H373, H401, H411
GHS precautionary statements	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)
Autoignition; temperature	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

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 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]

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References

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

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[Booth-1] Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.