1,2-Dichlorobenzene
| 1,2-Dichlorobenzene[1] | |
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1,2-Dichlorobenzene |
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Other names
ortho-Dichlorobenzene,o-Dichlorbenzene, odcb |
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| Identifiers | |
| CAS number | 95-50-1  |
| ChemSpider | 13837988 |
| UNII | 6PJ93I88XL |
| KEGG | C14328 |
| ChEBI | CHEBI:35290 |
| ChEMBL | CHEMBL298461 |
| Jmol-3D images | Image 1 Image 2 |
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| 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 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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.
[edit] 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]
[edit] See also
[edit] References
- ^ Merck Index, 11th Edition, 3044
- ^ Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.
- ^ Technical Order 2J-1-13
