2-Nitrochlorobenzene

2-Nitrochlorobenzene

Names
Preferred IUPAC name 1-Chloro-2-nitrobenzene
Other names 2-Chloronitrobenzene
Identifiers
CAS Number	88-73-3
3D model (JSmol)	Interactive image
ChemSpider	13853953
ECHA InfoCard	100.001.686
CompTox Dashboard (EPA)	DTXSID0020280
InChI InChI=1S/C6H4ClNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H Key: BFCFYVKQTRLZHA-UHFFFAOYSA-N InChI=1/C6H4ClNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H Key: BFCFYVKQTRLZHA-UHFFFAOYAA
SMILES C1=CC=C(C(=C1)[N+](=O)[O-])Cl
Properties
Chemical formula	C6H4ClNO2
Molar mass	157.55 g·mol−1
Appearance	Yellow crystals
Density	1.368 g/mL
Melting point	33 °C (91 °F; 306 K)
Boiling point	245.5 °C (473.9 °F; 518.6 K)
Solubility in water	Insoluble
Solubility in other solvents	Highly soluble in diethyl ether, benzene, and hot ethanol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Toxic, Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Nitrochlorobenzene is an organic compound with the formula ClC₆H₄NO₂. It is a yellow crystalline solid that is important as a precursor to other compounds due to the two reactive sites present on the molecule.

Synthesis

Nitrochlorobenzene is typically synthesized by nitration of chlorobenzene in the presence of sulfuric acid:

C₆H₅Cl + HNO₃ → O₂NC₆H₄Cl + H₂O

This reaction affords a mixture of isomers. Using an acid ratio of 30/56/14, the product mix is typically 34-36% 2-nitrochlorobenzene and 63-65% 4-nitrochlorobenzene, with only about 1% 3-nitrochlorobenzene.

Reactions

Alkylation and electrophilic aromatic substitution can occur at the chlorinated carbon center, and a diverse array of reactions can be carried out using the nitro group. 2-Nitrochlorobenzene can be reduced to 2-chloroaniline with Fe/HCl mixture, the Bechamp reduction.

Applications

2-Nitrochlorobenzene is not valuable in itself but is a precursor to other useful compounds. The compound is particularly useful because both of its reactive sites can be utilized to create further compounds that are mutually ortho. Its derivative 2-chloroaniline is a precursor to 3,3’-dichlorobenzidine, itself a precursor to many dyes and pesticides.