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Names | |||
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IUPAC name
1,2-Dichlorobenzene
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Other names
ortho-Dichlorobenzene, o-Dichlorobenzene, odcb, o-Dichlorobenzol
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Identifiers | |||
95-50-1 | |||
3D model (Jmol) |
Interactive image Interactive image |
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ChEBI | CHEBI:35290 | ||
ChEMBL | ChEMBL298461 | ||
ChemSpider | 13837988 | ||
ECHA InfoCard | 100.002.206 | ||
EC Number | 202-425-9 | ||
KEGG | C14328 | ||
PubChem | 7239 | ||
UNII | 6PJ93I88XL | ||
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Properties | |||
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) | ||
0.01% | |||
Vapor pressure | 1 mmHg (20° C) | ||
-84.26·10−6 cm3/mol | |||
Hazards | |||
Safety data sheet | External MSDS | ||
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 (151 °F; 339 K) | ||
Explosive limits | 2.2%-9.2% | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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500 mg/kg (oral, rat, rabbit) 2000 mg/kg (oral, guinea pig) 4386 mg/kg (oral, mouse) |
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LCLo (lowest published)
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1000 ppm (guinea pig, 20 hr) 800 ppm (guinea pig, 24 hr) 821 ppm (rat, 7 hr) |
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US health exposure limits (NIOSH): | |||
PEL (Permissible)
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C 50 ppm (300 mg/m3) | ||
REL (Recommended)
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C 50 ppm (300 mg/m3) | ||
IDLH (Immediate danger)
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200 ppm | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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what is ?) | (|||
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.
1,2-Dichlorobenzene is obtained as a side-product of the production of chlorobenzene:
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.
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.