1,2-Dichlorobenzene

1,2-Dichlorobenzene[1]
IUPAC name 1,2-Dichlorobenzene
Other names ortho-Dichlorobenzene,o-Dichlorbenzene, odcb
Identifiers
CAS number	95-50-1 Y
ChemSpider	13837988 Y
UNII	6PJ93I88XL Y
KEGG	C14328 Y
ChEBI	CHEBI:35290 Y
ChEMBL	CHEMBL298461 Y
Jmol-3D images	Image 1 Image 2
SMILES c1ccc(c(c1)Cl)Cl c1ccc(c(c1)Cl)Cl
InChI InChI=1S/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H Y Key: RFFLAFLAYFXFSW-UHFFFAOYSA-N Y InChI=1/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H Key: RFFLAFLAYFXFSW-UHFFFAOYAE
Properties
Molecular formula	C6H4Cl2
Molar mass	147.01 g/mol
Density	1.30 g/cm³
Melting point	-17.03 °C, 256 K, 1 °F
Boiling point	180.5 °C, 454 K, 357 °F
Hazards
MSDS	http://www.sigmaaldrich.com/catalog/DisplayMSDSContent.do
Ingestion hazard	Toxic if swallowed
Inhalation hazard	Causes respiratory tract irritation
Eye hazard	Causes eye irritation
Skin hazard	Causes skin irritation
Flash point	66 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an organic compound with the formula C₆H₄Cl₂. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine centers.

Production and uses

1,2-Dichlorobenzene is obtained as a side-product of the production of chlorobenzene:

C₆H₅Cl + Cl₂ → C₆H₄Cl₂ + HCl

The reaction also affords the 1,4- and small amounts of the 1,3-isomer. The 1,4- isomer is preferred over the 1,2- isomer due to steric hindrance. The 1,3- isomer is uncommon because chlorine, like all halogens, are ortho/para- directors in terms of electrophilic aromatic substitution and the 1,3- isomer is a meta- compound.

It is mainly used as a precursor to 1,2-dichloro-4-nitrobenzene, an intermediate in the synthesis of agrochemicals.^[2] In terms of niche applications, 1,2-dichlorobenzene is a versatile, high-boiling solvent. It is a preferred solvent for dissolving and working with fullerenes. It is an insecticide for termites and locust borers.^{[citation needed]}

1,2-Dichlorobenzene is also used in softening and removing carbon-based contamination on metal surfaces.^[3]

See also

• Chlorobenzene
• 1,4-Dichlorobenzene

References

1. ^ Merck Index, 11th Edition, 3044
2. ^ Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.
3. ^ Technical Order 2J-1-13