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516-12-1 molecular structure
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1-iodopyrrolidine-2,5-dione

ChemBase ID: 22338
Molecular Formular: C4H4INO2
Molecular Mass: 224.98453
Monoisotopic Mass: 224.92867637
SMILES and InChIs

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

Cite this record

CBID:22338 http://www.chembase.cn/molecule-22338.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -0.093946725  LogD (pH = 7.4) -0.093946725 
Log P -0.093946725  Molar Refractivity 34.8222 cm3
Polarizability 14.219178 Å3 Polar Surface Area 37.38 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
~200 °C (dec.) expand Show data source
195°C(dec) expand Show data source
202(dec.)°C expand Show data source
202-206 °C(lit.) expand Show data source
ca 196°C dec. expand Show data source
Density
2.245 expand Show data source
Storage Warning
Harmful/Irritant/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold expand Show data source
IRRITANT, LIGHT SENSITIVE, MOISTURE SENSITIVE expand Show data source
Moisture & Light Sensitive expand Show data source
RTECS
WN2817000 expand Show data source
European Hazard Symbols
X expand Show data source
Irritant Irritant (Xi) expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
R:36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
26-36/37 expand Show data source
S:20-25-26-37/39 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H301-H315-H319-H335 expand Show data source
H302-H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A expand Show data source
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥97.0% (RT) expand Show data source
95% expand Show data source
97% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C4H4INO2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 05208506 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02155068 external link
Crystalline
Sigma Aldrich - 220051 external link
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 external link
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 external link
N-Iodosuccinimide is a iodo substituted succinimide that is used as an iodinating agent in chemical synthesis.

REFERENCES

REFERENCES

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  • • 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).
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PATENTS

PATENTS

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