1,2-Difluorobenzene

changed changed 477203790 David R. Lide, ed., CRC Handbook of Chemistry and Physics, 89th Edition (Internet Version 2009), CRC Press/Taylor and Francis, Boca Raton, FL. O-Difluorobenzene.svg correct ?? skin-invert 1,2-Difluorobenzene-3D-balls.png Difluorobenzene molecule bg-transparent 1,2-Difluorobenzene o-Difluorobenzeneortho-DifluorobenzeneDFB o-DFB1,2-DFB correct chemspider correct EBI 38583 9325 1/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H GOYDNIKZWGIXJT-UHFFFAOYAN correct chemspider 1S/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H correct chemspider GOYDNIKZWGIXJT-UHFFFAOYSA-N correct CAS 367-11-3 correct FDA AW7QGMW29C 9706 Fc1ccccc1F 6 4 2 colorless liquid 1.1599 g/cm3 -34 92 (insoluble) 1.14 g/L 1,2-Dichlorobenzene thumb | right | Ball-and-stick model of Difluorobenzene 1,2-Difluorobenzene, also known as DFB, is an aromatic compound with formula C6H4F2. This colorless flammable liquid is a solvent used in the electrochemical studies of transition metal complexes. Compared to most conventional halogenated aliphatic and aromatic solvents, it possesses an exceptionally high dielectric constant (ε0 = 13.8 at 300 K). Thus, it can be a suitable solvent for cationic, and/or highly electrophilic organometallic complexes.10.1039/C6CC09575E Organometallic chemistry using partially fluorinated benzenes 2017 Pike Sebastian D. Crimmin Mark R. Chaplin Adrian B. Chemical Communications 53 26 3615–3633 28304406 http://wrap.warwick.ac.uk/88073/1/WRAP-Organometallic-partially-benzenes-Chaplin-2017.pdf Synthesis Difluorobenzenes can be prepared by the Balz-Schiemann reaction, which entails conversion of diazonium tetrafluoroborate salts to their fluorides. The synthesis of 1,2-difluorobenzene starts with 2-fluoroaniline:10.1021/op300127x A Continuous Kilogram-Scale Process for the Manufacture of o-Difluorobenzene 2012 Yu Zhiqun Lv Yanwen Yu Chuanming Organic Process Research & Development 16 10 1669–1672 C6H4F(NH2) + HNO2 + HBF4 -> [C6H4F(N2)]BF4 + 2 H2O [C6H4F(N2)]BF4 -> C6H4F2 + N2 + BF3 The syntheses of 1,3- and 1,4-difluorobenzene proceed respectively from 1,3- and 1,4-diaminobenzene, which are doubly diazotized.10.1002/14356007.a11_349 Fluorine Compounds, Organic Ullmann's Encyclopedia of Industrial Chemistry 2000 Siegemund Günter Schwertfeger Werner Feiring Andrew Smart Bruce Behr Fred Vogel Herward McKusick Blaine 3527306730 Laboratory applications Organometallic derivatives of 1,2-difluorobenzene have been well developed. It is found to be a weaker base than benzene.10.1039/c6cc09575e Organometallic chemistry using partially fluorinated benzenes 2017 Pike Sebastian D. Crimmin Mark R. Chaplin Adrian B. Chemical Communications 53 26 3615–3633 28304406 http://wrap.warwick.ac.uk/88073/1/WRAP-Organometallic-partially-benzenes-Chaplin-2017.pdf 1,2-Difluorobenzene has been used as solvent for the electrochemical analysis of transition metal complexes. It is relatively chemically inert, weakly coordinating and has a relatively high dielectric constant. In contrast to acetonitrile, DMSO, and DMF it is a weakly coordinating solvent for metal complexes, . 10.1021/ic00319a032 1,2-Difluorobenzene: a relatively inert and noncoordinating solvent for electrochemical studies on transition-metal complexes 1989 O'toole Terrence R. Younathan Sullivan Meyer Inorganic Chemistry 28 3923 Janet N. B. Patrick Thomas J. 20 It has anaesthetic properties. 1,2-Difluorobenzene https://pubchem.ncbi.nlm.nih.gov/compound/9706 PubChem 11 February 2021 1,2-Difluorobenzene can be acylated to 3',4'-difluoropropiophenone.GB 1140754 3,4-difluorophenyl compounds 1969-01-22 Pfizer Ltd. Danilewicz John Christopher Szelke Michael References Category:Fluorobenzenes Category:Halogenated solvents Category:Aromatic solvents