1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an aryl chloride and isomer of dichlorobenzene 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 atoms.
It is mainly used as a precursor chemical in the synthesis of agrochemicals, as a preferred solvent for dissolving and working with fullerenes, as an insecticide, and in softening and removing carbon-based contamination on metal surfaces.
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 an ortho/para- director 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.[5] 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.[6]
1,2-Dichlorobenzene is also used in softening and removing carbon-based contamination on metal surfaces.[7]
^"CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): o-Dichlorobenzene - NIOSH Publications and Products". www.cdc.gov. 16 November 2017. Retrieved 22 April 2018.
^"CDC - NIOSH Pocket Guide to Chemical Hazards -o-Dichlorobenzene". www.cdc.gov. Retrieved 22 April 2018.
February 15, 2024
dichlorobenzene, orthodichlorobenzene, odcb, aryl, chloride, isomer, dichlorobenzene, with, formula, c6h4cl2, this, colourless, liquid, poorly, soluble, water, miscible, with, most, organic, solvents, derivative, benzene, consisting, adjacent, chlorine, atoms,. 1 2 Dichlorobenzene or orthodichlorobenzene ODCB is an aryl chloride and isomer of dichlorobenzene 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 atoms 1 2 Dichlorobenzene 1 Ball and stick model of the 1 2 dichlorobenzene molecule Space filling model of the 1 2 dichlorobenzene moleculeNamesPreferred IUPAC name 1 2 DichlorobenzeneOther names ortho Dichlorobenzene o Dichlorobenzene odcb o DichlorobenzolIdentifiersCAS Number 95 50 1 Y3D model JSmol Interactive imageInteractive imageChEBI CHEBI 35290 YChEMBL ChEMBL298461 YChemSpider 13837988 YECHA InfoCard 100 002 206EC Number 202 425 9KEGG C14328 YPubChem CID 7239UNII 6PJ93I88XL YCompTox Dashboard EPA DTXSID6020430InChI InChI 1S C6H4Cl2 c7 5 3 1 2 4 6 5 8 h1 4H YKey RFFLAFLAYFXFSW UHFFFAOYSA N YInChI 1 C6H4Cl2 c7 5 3 1 2 4 6 5 8 h1 4HKey RFFLAFLAYFXFSW UHFFFAOYAESMILES c1ccc c c1 Cl Clc1ccc c c1 Cl ClPropertiesChemical formula C6H4Cl2Molar mass 147 01 g molAppearance colourless liquidOdor Naphthalene likeDensity 1 30 g cm3Melting point 17 03 C 1 35 F 256 12 K Boiling point 180 19 C 356 34 F 453 34 K 3 Solubility in water 0 01 2 Vapor pressure 1 mmHg 20 C Magnetic susceptibility x 84 26 10 6 cm3 molRefractive index nD 1 54920Viscosity 1 0656 20 C HazardsOccupational safety and health OHS OSH Ingestion hazards Mildly toxicInhalation hazards Causes respiratory tract irritationEye hazards Causes eye irritationSkin hazards Causes skin irritationFlash point 66 C 151 F 339 K Explosive limits 2 2 9 2 2 Lethal dose or concentration LD LC LD50 median dose 500 mg kg oral rat rabbit 200 mg kg oral guinea pig 436 mg kg oral mouse 4 LCLo lowest published 1000 ppm guinea pig 20 hr 800 ppm guinea pig 24 hr 821 ppm rat 7 hr 4 NIOSH US health exposure limits PEL Permissible C 50 ppm 300 mg m3 2 REL Recommended C 50 ppm 300 mg m3 2 IDLH Immediate danger 200 ppm 2 Safety data sheet SDS External MSDSRelated compoundsRelated compounds 1 2 Difluorobenzene1 2 DibromobenzeneExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references It is mainly used as a precursor chemical in the synthesis of agrochemicals as a preferred solvent for dissolving and working with fullerenes as an insecticide and in softening and removing carbon based contamination on metal surfaces Contents 1 Production and uses 2 Safety 3 See also 4 ReferencesProduction and uses edit1 2 Dichlorobenzene is obtained as a side product of the production of chlorobenzene C6 H5 Cl Cl2 C6 H4 Cl2 HClThe 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 an ortho para director 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 5 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 6 1 2 Dichlorobenzene is also used in softening and removing carbon based contamination on metal surfaces 7 Safety editData 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 8 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 9 See also editChlorobenzenes different numbers of chlorine substituents and isomeric formsReferences edit Merck Index 11th Edition 3044 a b c d e NIOSH Pocket Guide to Chemical Hazards 0189 National Institute for Occupational Safety and Health NIOSH Rohac Vladislav Ruzicka Vlastimil Ruzicka Kvetoslav Aim Karel September 1998 Measurements of Saturated Vapor Pressure above the Liquid Phase for Isomeric Dichlorobenzenes and 1 2 4 Trichlorobenzene Journal of Chemical amp Engineering Data 43 5 770 775 doi 10 1021 je9701442 ISSN 0021 9568 a b o Dichlorobenzene National Institute for Occupational Safety and Health NIOSH 4 December 2014 Retrieved 6 March 2015 Gerald Booth 2007 Nitro Compounds Aromatic in Ullmann s Encyclopedia of Industrial Chemistry Wiley VCH Weinheim 2005 Battle of the Beetles 25 July 2011 Archived from the original on 2021 12 21 Retrieved 22 April 2018 via YouTube Technical Order 2J 1 13 CDC Immediately Dangerous to Life or Health Concentrations IDLH o Dichlorobenzene NIOSH Publications and Products www cdc gov 16 November 2017 Retrieved 22 April 2018 CDC NIOSH Pocket Guide to Chemical Hazards o Dichlorobenzene www cdc gov Retrieved 22 April 2018 Retrieved from https en wikipedia org w index php title 1 2 Dichlorobenzene amp oldid 1205955889, wikipedia, wiki, book, books, library,
