1,2-Dichlorobenzene

1,2-Dichlorobenzene

Names
IUPAC name 1,2-Dichlorobenzene
Other names ortho-Dichlorobenzene, o-Dichlorobenzene, odcb, o-Dichlorobenzol
Identifiers
CAS Number	95-50-1 Y
ChEBI	CHEBI:35290 Y
ChEMBL	ChEMBL298461 Y
ChemSpider	13837988 Y
EC Number	202-425-9
Jmol 3D model	Interactive image Interactive image
KEGG	C14328 Y
PubChem	7239
UNII	6PJ93I88XL Y
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
SMILES c1ccc(c(c1)Cl)Cl c1ccc(c(c1)Cl)Cl
Properties
Chemical formula	C6H4Cl2
Molar mass	147.01 g/mol
Density	1.30 g/cm3
Melting point	−17.03 °C (1.35 °F; 256.12 K)
Boiling point	180.5 °C (356.9 °F; 453.6 K)
Solubility in water	0.01%
Vapor pressure	1 mmHg (20° C)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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:

C
₆H
₅Cl + Cl
₂ → C
₆H
₄Cl
₂ + 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 it is a meta- compound, while chlorine, like all halogens, is a ortho/para- directors in terms of electrophilic aromatic substitution.

It is mainly used as a precursor to 1,2-dichloro-4-nitrobenzene, an intermediate in the synthesis of agrochemicals. 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, historically used by the United States Forest Service to combat widespread bark beetle outbreaks.

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

Safety

Data from human exposure to 1,2-dichlorobenzene shows that concentrations of 100 ppm have been reported to cause sporadic irritation of the eyes and respiratory tract. The Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health have set occupational exposure limits at a ceiling of 50 ppm, over an eight-hour workday.

See also

• Chlorobenzene
• 1,4-Dichlorobenzene