1-Iodpyrrolidin-2,5-dion

Bezeichnung:1-Iodpyrrolidin-2,5-dion

CAS-Nr516-12-1

Englisch Name:N-Iodosuccinimide

CBNumberCB0342078

SummenformelC4H4INO2

Molgewicht224.98

MOL-Datei516-12-1.mol

Synonyma

1-Iodpyrrolidin-2,5-dion

1-Iodpyrrolidin-2,5-dion physikalisch-chemischer Eigenschaften

Schmelzpunkt	202-206 °C(lit.)
Siedepunkt	249.6±23.0 °C(Predicted)
Dichte	2,245 g/cm³
storage temp.	2-8°C
Löslichkeit	Soluble in dioxane, tetrahydrfuran and acetonitrile. Insoluble in ether and carbon tetrachloride.
Aggregatzustand	Crystalline Powder
pka	-2.57±0.20(Predicted)
Farbe	White-yellow to brown
Wasserlöslichkeit	decomposes
Sensitive	Moisture Sensitive
Merck	14,5045
BRN	113917
Stabilität	Moisture Sensitive
InChIKey	LQZMLBORDGWNPD-UHFFFAOYSA-N
CAS Datenbank	516-12-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	22-36/37/38
S-Sätze:	26-36-37/39
WGK Germany	3
RTECS-Nr.	WN2817000
F	8-9
Hazard Note	Harmful/Keep Cold/Moisture Sensitive
TSCA	No
HazardClass	IRRITANT
HS Code	29251995

Gefahreninformationscode (GHS)

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
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.]

N-Iodosuccinimide Upstream-Materialien And Downstream Produkte

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

516-12-1, N-Iodosuccinimide Verwandte Suche:

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