1-iodopyrrolidine-2,5-dione

• ChemBase ID: 22338
• Molecular Formular: C4H4INO2
• Molecular Mass: 224.98453
• Monoisotopic Mass: 224.92867637
• SMILES: C1CC(=O)N(C1=O)I
• Canonical SMILES: IN1C(=O)CCC1=O
• InChI: InChI=1S/C4H4INO2/c5-6-3(7)1-2-4(6)8/h1-2H2
• InChIKey: LQZMLBORDGWNPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-iodopyrrolidine-2,5-dione
• IUPAC Traditional name: N-iodosuccinimide; NIS
• Synonyms: N-Iodosuccinimide; 1-Iodopyrrolidine-2,5-dione; 1-iodo-2,5-pyrrolidinedione; NIS; Succiniodimide; N-Iodosuccinimide; 1-Iodopyrrolidine-2,5-dione; 2,5-Dioxo-1-iodopyrrolidine; N-碘化丁二酰胺; N-碘代琥珀酰亚胺

Database IDs

• CAS Number: 516-12-1
• EC Number: 208-221-6
• MDL Number: MFCD00005512
• Beilstein Number: 113917
• Merck Index: 145045
• PubChem SID: 160985645; 24853162; 24881033
• PubChem CID: 120273

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.093946725
• LogD (pH = 7.4): -0.093946725
• Log P: -0.093946725
• Molar Refractivity: 34.8222 cm^3
• Polarizability: 14.219178 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~200 °C (dec.); 195°C(dec); 202(dec.)°C; 202-206 °C(lit.); ca 196°C dec.
• Density: 2.245

Safety Information

• Storage Warning: Harmful/Irritant/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold; IRRITANT, LIGHT SENSITIVE, MOISTURE SENSITIVE; Moisture & Light Sensitive
• RTECS: WN2817000
• European Hazard Symbols: X; Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; R:36/37/38
• Safety Statements: 26-36; 26-36/37; S:20-25-26-37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (RT); 95%; 97%
• Grade: purum
• Empirical Formula (Hill Notation): C4H4INO2

DETAILS

MP Biomedicals - 05208506

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02155068

Crystalline

Sigma Aldrich - 220051

Application
Highly substituted iodobenzenes prepared via an efficient 2-step process from 1,6-diynes.1 Used with TFA to chemoselectively hydrolyze thioglycosides to 1-hydroxyglycosides.2 Synthesis of vinyl sulfones from olefins and benzenesulfinic acid.3
Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 58070

Other Notes
Reagent for the oxidimetric titration of sulfur functions 1; Reagent for oxidations 2,3,4; Reagent for iodinations 5

Toronto Research Chemicals - I719900

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

REFERENCES

• Castanet, A.-S. et al.: Tetrahed. Lett., 43, 5047 (2002)
• Source of positive iodine. Iodinates methoxy benzenes and naphthalenes in acetonitrile, e.g. anisole gives 95% yield of 4-iodoanisole: Tetrahedron Lett., 37, 4081 (1996).
• In combination with TFA and TFA anhydride, iodinates 2,4-diethoxypyrimidines or N-alkyluracils specifically to their 5-iodo-derivatives: Synth. Commun., 18, 855 (1988). With triflic acid, the "superelectrophile" iodine(I) triflate is formed. This species will iodinate even deactivated aromatics, e.g. nitrobenzene to the m-iodo derivative: J. Org. Chem., 58, 3194 (1993).
• Alone or with a catalytic amount of triflic acid, is a powerful coupling agent in oligosaccharide synthesis, particularly for thioglycosyl donors; see, e.g.: Tetrahedron Lett., 34, 8523 (1993). For reviews, see: Chem. Rev., 93, 1503 (1993); Contemp. Org. Synth., 3, 173 (1996).
• In the presence of triphenylphosphine or triphenyl phosphite, converts alcohols to iodides stereoselectively with inversion: Tetrahedron Lett., 3937 (1973). See also: Carbohydr. Res., 24, 45 (1972).
• In combination with the phase-transfer catalyst, Tetra-n-butylammonium iodide, A15484, oxidizes alcohols to carbonyl compounds in high yield under neutral conditions: Synthesis, 394 (1981). Glycols are cleaved to carbonyl compounds; the rate of reaction is increased by u.v. irradiation: J. Org. Chem., 46, 1927 (1981). Similarly, ɑ-hydroxyacids are oxidatively decarboxylated to ketones: J. Org. Chem., 47, 3006 (1982).
• Oxidative coupling of dianions of acyclic tertiary amides gives a stereoselective preparation of ?-lactams: J. Org. Chem., 57, 1864 (1992):
  
• Has been used in the construction of disulfide bridges in cystine peptides, from cysteine in a DMF-dichloromethane solvent: J. Org. Chem., 58, 3003 (1993).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 960 (2006).
• With K₂CO₃ in MeOH, aldehydes can be oxidized directly to methyl esters: J. Org. Chem., 54, 1213 (1989).