1,2-Dichlorobenzene

changed changed 477203514 Merck Index, 11th Edition, 3044 1,2-Dichlorobenzene O-Dichlorobenzene-2D-skeletal.svg Skeletal structure of 1,2-Dichlorobenzene 150px skin-invert 1,2-Dichlorobenzene-Mercury-3D-bs.png Ball-and-stick model of the 1,2-dichlorobenzene molecule 150px bg-transparent 1,2-Dichlorobenzene-Mercury-3D-sf.png Space-filling model of the 1,2-dichlorobenzene molecule 150px bg-transparent 1,2-Dichlorobenzene ortho-Dichlorobenzene, o-Dichlorobenzene, odcb, o-Dichlorobenzol 7239 correct chemspider correct EBI 35290 13837988 correct kegg C14328 1/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H RFFLAFLAYFXFSW-UHFFFAOYAE c1ccc(c(c1)Cl)Cl correct EBI 298461 correct chemspider 1S/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H correct chemspider RFFLAFLAYFXFSW-UHFFFAOYSA-N 95-50-1 202-425-9 correct CAS correct FDA 6PJ93I88XL c1ccc(c(c1)Cl)Cl 6 4 2 colourless liquid Naphthalene-like 1.30 g/cm3 −17.03 180.19 Roháč Vladislav Růžička Vlastimil Růžička Květoslav Aim Karel September 1998 Measurements of Saturated Vapor Pressure above the Liquid Phase for Isomeric Dichlorobenzenes and 1,2,4-Trichlorobenzene Journal of Chemical & Engineering Data en 43 5 770–775 10.1021/je9701442 0021-9568 0.01% 1 mmHg (20°C) 1.0656 (20 °C) −84.26·10−6 cm3/mol 1.54920 66 Causes skin irritation Causes eye irritation Causes respiratory tract irritation Mildly toxic External MSDS C 50 ppm (300 mg/m3)0189 2.2%–9.2% 200 ppm 500 mg/kg (oral, rat, rabbit) 200 mg/kg (oral, guinea pig)436 mg/kg (oral, mouse) https://www.cdc.gov/niosh/idlh/95501.html o-Dichlorobenzene National Institute for Occupational Safety and Health (NIOSH) 4 December 2014 6 March 2015 C 50 ppm (300 mg/m3) 1000 ppm (guinea pig, 20 hr)800 ppm (guinea pig, 24 hr)821 ppm (rat, 7 hr) 1,2-Difluorobenzene1,2-Dibromobenzene 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, substituted with 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. Production and uses 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 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.Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. 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.https://www.youtube.com/watch?v=axs2jR2HC6I https://ghostarchive.org/varchive/youtube/20211221/axs2jR2HC6I 2021-12-21 live Battle of the Beetles 25 July 2011 22 April 2018 YouTube 1,2-Dichlorobenzene is also used in softening and removing carbon-based contamination on metal surfaces.Technical Order 2J-1-13 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.https://www.cdc.gov/niosh/idlh/95501.html CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): o-Dichlorobenzene - NIOSH Publications and Products 16 November 2017 www.cdc.gov 22 April 2018 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.https://www.cdc.gov/niosh/npg/npgd0189.html CDC - NIOSH Pocket Guide to Chemical Hazards -o-Dichlorobenzene www.cdc.gov 22 April 2018 See also Chlorobenzenes—different numbers of chlorine substituents and isomeric forms References Category:Dichlorophenyl compounds Category:Organochloride insecticides Category:Halogenated solvents Category:Aromatic solvents