Diiodobenzenes

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Diiodobenzenes
Surname 1,2-diiodobenzene 1,3-diiodobenzene 1,4-diiodobenzene
other names o -diiodobenzene m -diiodobenzene p -diiodobenzene
Structural formula Structure of o-diiodobenzene Structure of m-diiodobenzene Structure of p-diiodobenzene
CAS number 615-42-9 626-00-6 624-38-4
PubChem 11994 12270 12208
Molecular formula C 6 H 4 I 2
Molar mass 329.91 g mol −1
Physical state liquid firmly
Melting point 27 ° C 40 ° C 131-133 ° C
boiling point 287 ° C 285 ° C 285 ° C
density 2.524 g cm −3
GHS
labeling
05 - Corrosive 07 - Warning
danger
07 - Warning
Caution
no GHS pictograms
H and P phrases 315-318-335 315-319-335 no H-phrases
no EUH phrases no EUH phrases no EUH phrases
261-280-305 + 351 + 338 261-305 + 351 + 338 no P-phrases

In chemistry , the diiodobenzenes form a group of substances consisting of a benzene ring with two iodine atoms  (–I) as substituents . Their different arrangement ( ortho , meta or para ) results in three constitutional isomers with the empirical formula C 6 H 4 I 2 .

properties

The boiling points of the three isomers are relatively close to one another, while their melting points differ more clearly. The 1,4-diiodobenzene, which has the highest symmetry, has the highest melting point.

presentation

The diiodobenzenes can be obtained from the corresponding diaminobenzenes by diazotization and subsequent reaction with copper (I) iodide .

Individual evidence

  1. ^ A b Morrison / Boyd: Textbook of Organic Chemistry , 3rd Edition, VCH, Weinheim 1986, ISBN 3-527-26067-6 , p. 1113.
  2. ↑ a b CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
  3. ↑ a b c data sheet 1,4-diiodobenzene from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).
  4. ↑ a b data sheet 1,2-diiodobenzene from Sigma-Aldrich , accessed on February 25, 2011 ( PDF ).
  5. ↑ Data sheet 1,3-diiodobenzene from Sigma-Aldrich , accessed on February 25, 2011 ( PDF ).

literature

  • Abil E. Aliev, Kenneth DM Harris, Xavier Alcobéa, Eugènia Estop: "Dynamic properties of p -diiodobenzene investigated by solid-state 2 H and 13 C nuclear magnetic resonance spectroscopy", in: J. Chem. Soc., Faraday Trans. , 1993 , 89 , pp. 3797-3800; doi : 10.1039 / FT9938903797 .
  • TV Magdesieva, II Kukhareva, GA Artamkina, IP Beletskaya, KP Butin: “Electrochemically induced aromatic nucleophilic substitution in p -diiodobenzene with [(η 5 -C 5 H 5 ) Fe (CO) 2 ] - and [(η 5 -C 5 H 5 ) W (CO) 3 ] - -anions ”, in: Journal of Organometallic Chemistry , 1995 , 487  (1-2), pp. 163-166; doi : 10.1016 / 0022-328X (94) 05077-O .
  • Linda C. Brazdil, Carlo J. Cutler: “Selective Production of Diiodobenzene and Iodobenzene from Benzene”, in: J. Org. Chem. , 1996 , 61  (26), pp. 9621-9622; doi : 10.1021 / jo961493m .