1,2-Dichlorobenzene

From Wikipedia, the free encyclopedia
  (Redirected from O-Dichlorobenzene)
Jump to: navigation, search
1,2-Dichlorobenzene[1]
1,2-Dichlorobenzene Ball-and-stick model of 1,2-dichlorobenzene
Identifiers
CAS number 95-50-1 YesY
ChemSpider 13837988 YesY
UNII 6PJ93I88XL YesY
EC-number 202-425-9
KEGG C14328 YesY
ChEBI CHEBI:35290 YesY
ChEMBL CHEMBL298461 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular 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)
Hazards
MSDS 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)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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[edit]

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

C
6
H
5
Cl
+ Cl
2
C
6
H
4
Cl
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 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, historically used by the United States Forest Service to combat widespread bark beetle outbreaks.[3]

1,2-Dichlorobenzene is also used in softening and removing carbon-based contamination on metal surfaces.[4]

Safety[edit]

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.[5] 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.[6]

See also[edit]

References[edit]

  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. ^ http://www.youtube.com/watch?v=axs2jR2HC6I
  4. ^ Technical Order 2J-1-13
  5. ^ CDC - Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs)
  6. ^ CDC - NIOSH Pocket Guide to Chemical Hazards