3,5-diiodosalicylic acid

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Structural formula
Structural formula of 3,5-diiodosalicylic acid
General
Surname 3,5-diiodosalicylic acid
other names

3,5-diiodo-2-hydroxybenzoic acid

Molecular formula C 7 H 4 I 2 O 3
Brief description

light brown powder

External identifiers / databases
CAS number 133-91-5
EC number 205-124-0
ECHA InfoCard 100.004.659
PubChem 8631
ChemSpider 8310
DrugBank DB04674
Wikidata Q223023
properties
Molar mass 389.91 g · mol -1
Physical state

firmly

Melting point

232–233 ° C ( decomposition )

solubility
  • poor in water (0.19 g l −1 at 25 ° C)
  • soluble in alcohol and ether
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302-312-315-319-332-335
P: 261-280-305 + 351 + 338
Toxicological data

500 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3,5-Diiodosalicylic acid is an organic chemical compound that belongs to the group of phenols as well as the group of aromatic carboxylic acids . It is therefore a phenolic acid .

presentation

3,5-Diiodosalicylic acid can be prepared from salicylic acid by iodination with iodine chloride in glacial acetic acid .

Production of 3,5-diiodosalicylic acid by iodination of salicylic acid in glacial acetic acid

Furthermore, the synthesis from salicylic acid and elemental iodine in ethanolic solution is possible by adding hydrogen peroxide .

toxicity

In animal experiments it was found that 3,5-diiodosalicylic acid is not toxic.

use

3,5-diiodosalicylic acid is a starting product for the production of rafoxanide , which is used as a drug against tapeworm infestation in pets. In biochemistry , 3,5-diiodosalicylic acid is of interest because, in contrast to unsubstituted salicylic acid, it has a stronger bond to transthyretin .

Reactions

Further iodination of 3,5-diiodosalicylic acid in the presence of potassium hydroxide fails and the acid group 2,4,6-triiodophenol is split off . 3,5-Diiodosalicylic acid turns a ferric chloride solution violet.

Derivatives

Acetylation of 3,5-diiodosalicylic acid leads to diiodo aspirin, the anticoagulant effect of which is greater than that of unsubstituted aspirin . 3,5-diiodo-4- aminosalicylic acid , which is produced by iodination of 4-aminosalicylic acid with iodine chloride in glacial acetic acid, has been used in the treatment of tuberculosis .

Salts

The sodium and ammonium salts of 3,5-diiodosalicylic acid are water-soluble. The salts with rare earth metals have the general formula X (I 2 Sal) 3 · 5 H 2 O, where X = La , Ce , Pr , Nd , or X (I 2 Sal) 3 · 4 H 2 O, where X = Sm , Ho , Yb , Y . These salts are not soluble in water, dimethylformamide , dimethyl sulfoxide and in non-polar solvents, but are soluble in ethanol , methanol and acetone .

The potassium salt of 3,5-diiodosalicylic acid is registered with the CAS number 17274-17-8, the lithium salt under CAS number 42935-32-0.

The separation of the 5-iodosalicylic acid formed as an intermediate product in the synthesis is possible via the barium salt, which in the case of 5-iodosalicylic acid dissolves well in water, whereas 3,5-diiodosalicylate is sparingly soluble.

Individual evidence

  1. ↑ a b c data sheet 3,5-diiodosalicylic acid from Sigma-Aldrich , accessed on June 18, 2017 ( PDF ).Template: Sigma-Aldrich / name not given
  2. ↑ a b c data sheet 3,5-diiodosalicylic acid (PDF) from Merck , accessed on March 6, 2010.
  3. ^ A b c d Henry Watts: A dictionary of chemistry . 1868, p. 157 ( limited preview in Google Book search).
  4. ^ GH Woollett and WW Johnson: 2-Hydroxy-3,5-Diiodobenzoic Acid In: Organic Syntheses . 14, 1934, p. 52, doi : 10.15227 / orgsyn.014.0052 ; Coll. Vol. 2, 1943, p. 343 ( PDF ).
  5. ↑ L. Jurd: The Iodination of aromatic compounds. IV. The Iodination of aromatic Hydrocarbons and Nuclear-substituted phenols , in: Australian Journal of Scientific Research, Series A: Physical Sciences , 1950 , 3 , p. 587. bibcode : 1950AuSRA ... 3..587J .
  6. ^ S. Mittler, GH Benham: Nutritional availability of iodine from several insoluble compounds , in: J. Nutrition , 1953 , pp. 53-58; (PDF; 296 kB) .
  7. ↑ alchemchina.com: Pharmaceutical intermediates ( Memento June 20, 2012 in the Internet Archive ), accessed November 19, 2016.
  8. ↑ Entry on Rafoxanide at chemicalland21.com, accessed on June 18, 2017.
  9. ↑ L. Gales, MR Almeida, G. Arsequell, G. Valencia, MJ Saraiva, AM Damas: Iodination of salicylic acid improves its binding to transthyretin. In: Biochimica et Biophysica Acta . Volume 1784, Number 3, March 2008, pp. 512-517, doi : 10.1016 / j.bbapap.2007.11.014 , PMID 18155178 .
  10. ↑ TJ Mende: Enhancement of the antihemostatic effect of acetylsalicylic acid by ring iodination , in: Pharmacology , 1972 , 7 , pp. 249-254; doi : 10.1159 / 000136295 .
  11. ^ DS Bhate, TB Panse, K. Venkataraman: Antitubercular compounds, Part II, 3,5-Diiodo-4-aminosalicylic acid, 4-Amino-O-acetylsalicylic acid and other derivatives of 4-aminosalicylic acid , 1950 ; 32: 357. doi : 10.1007 / BF03172507 (PDF; 133 kB) .
  12. ↑ a b c D. K. Koppikar, S. Soundararajan: "Diiodosalicylates of the rare earths", in: Curr. Sci. , 1976 , 45  (1), p. 3; (PDF; 237 kB) .