To install click the Add extension button. That's it.

The source code for the WIKI 2 extension is being checked by specialists of the Mozilla Foundation, Google, and Apple. You could also do it yourself at any point in time.

4,5
Kelly Slayton
Congratulations on this excellent venture… what a great idea!
Alexander Grigorievskiy
I use WIKI 2 every day and almost forgot how the original Wikipedia looks like.
Live Statistics
English Articles
Improved in 24 Hours
Added in 24 Hours
What we do. Every page goes through several hundred of perfecting techniques; in live mode. Quite the same Wikipedia. Just better.
.
Leo
Newton
Brights
Milds

1,2-Difluorobenzene

From Wikipedia, the free encyclopedia

1,2-Difluorobenzene[1]
Difluorobenzene molecule
Names
Preferred IUPAC name
1,2-Difluorobenzene
Other names
o-Difluorobenzene
ortho-Difluorobenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.074 Edit this at Wikidata
UNII
  • InChI=1S/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H checkY
    Key: GOYDNIKZWGIXJT-UHFFFAOYSA-N checkY
  • InChI=1/C6H4F2/c7-5-3-1-2-4-6(5)8/h1-4H
    Key: GOYDNIKZWGIXJT-UHFFFAOYAN
  • Fc1ccccc1F
Properties
C6H4F2
Molar mass 114.093 g/mol
Appearance colorless liquid
Density 1.1599 g/cm3
Melting point −34 °C (−29 °F; 239 K)
Boiling point 92 °C (198 °F; 365 K)
(insoluble) 1.14 g/L
Related compounds
Related compounds
1,2-Dichlorobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.[2]

YouTube Encyclopedic

  • 1/1
    Views:
    15 772
  • Lecture 11. Magnetic Equivalence, Spin Systems, and Pople Notation.

Transcription

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:[3]

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.[4]

Laboratory applications

Organometallic derivatives of 1,2-difluorobenzene have been well developed. It is found to be a weaker base than benzene.[5]

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. It is a weakly coordinating for metal complexes, in contrast to acetonitrile, DMSO, and DMF.[6]

It has anaesthetic properties.[7]

1,2-Difluorobenzene can be acylated to 3',4'-difluoropropiophenone.[8]

References

  1. ^ David R. Lide, ed., CRC Handbook of Chemistry and Physics, 89th Edition (Internet Version 2009), CRC Press/Taylor and Francis, Boca Raton, FL.
  2. ^ Pike, Sebastian D.; Crimmin, Mark R.; Chaplin, Adrian B. (2017). "Organometallic chemistry using partially fluorinated benzenes" (PDF). Chemical Communications. 53 (26): 3615–3633. doi:10.1039/C6CC09575E. PMID 28304406.
  3. ^ Yu, Zhiqun; Lv, Yanwen; Yu, Chuanming (2012). "A Continuous Kilogram-Scale Process for the Manufacture of o-Difluorobenzene". Organic Process Research & Development. 16 (10): 1669–1672. doi:10.1021/op300127x.
  4. ^ Siegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2000). "Fluorine Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_349. ISBN 3527306730.
  5. ^ Pike, Sebastian D.; Crimmin, Mark R.; Chaplin, Adrian B. (2017). "Organometallic chemistry using partially fluorinated benzenes" (PDF). Chemical Communications. 53 (26): 3615–3633. doi:10.1039/c6cc09575e. PMID 28304406.
  6. ^ O'toole, Terrence R.; Younathan, Janet N.; Sullivan, B. Patrick; Meyer, Thomas J. (1989). "1,2-Difluorobenzene: a relatively inert and noncoordinating solvent for electrochemical studies on transition-metal complexes". Inorganic Chemistry. 28 (20): 3923. doi:10.1021/ic00319a032.
  7. ^ "1,2-Difluorobenzene". PubChem. Retrieved 11 February 2021.
  8. ^ GB 1140754, Danilewicz, John Christopher & Szelke, Michael, "3,4-difluorophenyl compounds", published 1969-01-22, assigned to Pfizer Ltd. 
This page was last edited on 28 January 2024, at 00:36
Basis of this page is in Wikipedia. Text is available under the CC BY-SA 3.0 Unported License. Non-text media are available under their specified licenses. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc. WIKI 2 is an independent company and has no affiliation with Wikimedia Foundation.