1-Iodpyrrolidin-2,5-dion

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H315：Verursacht Hautreizungen.

  H317：Kann allergische Hautreaktionen verursachen.

  H319：Verursacht schwere Augenreizung.

  H341：Kann vermutlich genetische Defekte verursachen.

  H410：Sehr giftig für Wasserorganismen mit langfristiger Wirkung.

• Sicherheit

  P201：Vor Gebrauch besondere Anweisungen einholen.

  P273：Freisetzung in die Umwelt vermeiden.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P302+P352：BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

  P308+P313：BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

N-Iodosuccinimide Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R22:Gesundheitsschädlich beim Verschlucken.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

• S-Sätze Betriebsanweisung:

  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
  S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.

• Chemische Eigenschaften

  white-yellow to brown crystalline powder

• Verwenden

  N-Iodosuccinimide is used in the preparation of vinyl sulfones from olefins and benzenesulfinic acid. It acts as a source for I+ and involved in Hunsdiecker reactions for the conversion of cinnamic acids, and propiolic acids to the corresponding alfa-halostyrenes and 1-halo-1-alkynes respectively. It is also used to hydrolyze thioglycosides to 1-hydroxyglycosides with triluoroacetic acid. It is involved in the preparation of iodobenzene from 1,6-diynes. Further, it acts as an iodinating agent in chemical synthesis.

• Verwenden

  Iodination of ketones and aldehydes.
  Highly substituted iodobenzenes prepared via an efficient 2-step process from 1,6-diynes.
  Used with TFA to chemoselectively hydrolyze thioglycosides to 1-hydroxyglycosides.
  Synthesis of vinyl sulfones from olefins and benzenesulfinic acid.

• Verwenden

  N-Iodosuccinimide is a iodo substituted succinimide that is used as an iodinating agent in chemical synthesis.

• synthetische

  To a solution of 39.2g of succinimide in 1200ml of boiling water was added 51.0g of freshly precipitated silver oxide, the mixture was filtered and the silver salt was allowed to crystallize. Filtration and washing with cold water furnished 45.0g of the silver salt of succinimide suitable for the iodination step.
  The finely powdered salt (49.5g) was added in portions with stirring to a solution of 50.8g of iodine in 300ml of acetone, the temperature being maintained at 5-10°C. After decolorization (30 min.), the silver iodide was filtered, the solvent was removed under reduced pressure at room temperature and the residue was washed with ether, yielding 43g of N-iodosuccinimide with mp 189-191°C. An analytical sample (85% recovery) was obtained by dissolving in the minimum quantity of hot dioxane and precipitating with carbon tetrachloride; colorless needles, mp 200-201°C.
  Ref: JACS 75, 3493 (1953)

• Definition

  ChEBI: N-iodosuccinimide is a five-membered cyclic dicarboximide compound having an iodo substituent on the nitrogen atom. It is a dicarboximide and a pyrrolidinone. It derives from a succinimide.

• Reaktionen

  N-Iodosuccinimide (NIS) is an iodinating agent that is used for various electrophilic iodinations and as source for iodine in radical reactions.
  N-Iodosuccinimide is the least reactive of the N-haloamides in aromatic substitution. N-Iodosuccinimide does not act as an iodinating agent in pure dimethyl sulfoxide or N-ethylacetamide. On the other hand, butyl disulfide and a number of other sulfur-containing compounds are effective catalysts at low concentration for the iodination of guanosine derivatives using N-iodosuccinimide. This catalytic effect is observed when dimethyl sulfoxide is used as the solvent,but not when N-ethylacetamide is used.
  https://www.organic-chemistry.org/chemicals/oxidations/n-iodosuccinimide-nis.shtm

• Synthesis Reference(s)

  Journal of the American Chemical Society, 75, p. 3493, 1953 DOI: 10.1021/ja01110a055
  Organic Syntheses, Coll. Vol. 5, p. 663, 1973
  Tetrahedron Letters, 25, p. 233, 1984 DOI: 10.1016/S0040-4039(00)99848-4

• Synthese

  

  123-56-8

  

  516-12-1

  The general procedure for synthesizing N-iodosuccinimide from succinimide was as follows: a mixture of succinimide (1.0 g, 10.1 mmol), iodobenzene diacetate (1.95 g, 6.06 mmol), iodine (1.67 g, 6.57 mmol), and benzene (20 mL) was stirred and reacted for 15 hours at room temperature. Subsequently, the reaction mixture was cooled and kept at 0 to 5 °C for 1 hour. The precipitated solid product was filtered, the filter cake was washed with cold benzene and finally dried under vacuum to give 2.2 g of N-iodosuccinimide in 99% yield.

• läuterung methode

  Crystallise it from dioxane/CCl4. It iodinates arenes in triflic acid. [Olah et al J Org Chem 58 3194 1993, Beilstein 21/9 V 544.]

• Einzelnachweise

  [1] Patent: WO2015/68159, 2015, A2. Location in patent: Paragraph 00171-00172
  [2] Journal of Organometallic Chemistry, 1983, vol. 255, # 3, p. 295 - 298

N-Iodosuccinimide Upstream-Materialien And Downstream Produkte

1-Iodpyrrolidin-2,5-dion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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