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516-12-1

Basic Information
CAS No.: 516-12-1
Name: N-Iodosuccinimide
Article Data: 20
Molecular Structure:
Molecular Structure of 516-12-1 (N-Iodosuccinimide)
Formula: C4H4INO2
Molecular Weight: 224.986
Synonyms: 5-21-09-00544 (Beilstein Handbook Reference);Succinimide, N-iodo-;N-Iodosuccinimide 99%;2,5-Pyrrolidinedione, 1-iodo- (9CI);1-Iodopyrrolidine-2,5-dione;Succiniodimide;
EINECS: 208-221-6
Density: 2.31 g/cm3
Melting Point: 173 -175
Boiling Point: 249.6 °C at 760 mmHg
Flash Point: 104.8 °C
Solubility: decomposes in water
Appearance: white-yellow to brown crystalline powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38
Safety: 26-36-37/39
PSA: 37.38000
LogP: 0.42330
Synthetic route
123-56-8

Succinimide

516-12-1

N-iodo-succinimide

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; iodine In benzene at 20℃; for 15h; Concentration; Solvent; Time; Darkness;99%
With Iodine monochloride; bis(tri-n-butyltin)oxide 1.) benzene, reflux, 4 h, 2.) CH3CN; Yield given. Multistep reaction;
128-09-6

N-chloro-succinimide

516-12-1

N-iodo-succinimide

Conditions
ConditionsYield
With sodium iodide In acetone for 0.25h;89%
With sodium iodide In acetone for 2h;44%
With sodium iodide In acetone for 0.25h;
With sodium iodide In N,N-dimethyl-formamide at 20℃; for 1h;
With sodium iodide In acetone for 0.25h;
128-08-5

N-Bromosuccinimide

516-12-1

N-iodo-succinimide

Conditions
ConditionsYield
With iodine In tetrachloromethane at 40 - 50℃; for 1h;80%
With iodine In (2)H8-toluene at 20℃;
With iodine In tetrachloromethane at 40 - 55℃;
123-56-8

Succinimide

7553-56-2

iodine

67-64-1

acetone

516-12-1

N-iodo-succinimide

Conditions
ConditionsYield
Ausgangstoff ist Succinimid-silber;
mercury comp bond of succinimide

mercury comp bond of succinimide

516-12-1

N-iodo-succinimide

Conditions
ConditionsYield
With acetic acid ester; iodine
silver compound of succinimide

silver compound of succinimide

516-12-1

N-iodo-succinimide

Conditions
ConditionsYield
With iodine; acetone
With diethyl ether; iodine
silver-compound of succinimide

silver-compound of succinimide

516-12-1

N-iodo-succinimide

Conditions
ConditionsYield
With iodine; ethyl acetate
With iodine; acetone
With 1,4-dioxane; iodine
516-12-1

N-iodo-succinimide

167033-03-6

((C2H5)2C2B4H4)Nb(Cl)2(C5H5)

266323-96-0

C5H5Cl2Nb((C2H5)2C2B4H3I)

Conditions
ConditionsYield
In tetrahydrofuran Nb-complex was dissolved in THF, ligand was added, shaken for 5 min under inert atm.; after 10 min solvent was removed by rotary evaporator, residue was redissolved in CH2Cl2, flash-chromd. on silica, solvent was removed; elem. anal.;100%
516-12-1

N-iodo-succinimide

(η5-C5H5)Co(Et2C2B3H5)

(C5H5)Co((C2H5)2C2B3H3I2)

Conditions
ConditionsYield
In not given inert atmosphere;100%
516-12-1

N-iodo-succinimide

(C5(CH3)5)Co((CH3CH2)2C2B3H4Br)

(η(5)-C5Me5)Co(2,3-Et2C2B3H3-4-Br-6-I)

Conditions
ConditionsYield
In tetrahydrofuran inert atmosphere; stirring (15 min); evapn., chromy. (SiO2, hexane);100%
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    N-Iodosuccinimide Product Name: N-Iodosuccinimide Molecular Weight: 224.98 CAS NO: 516-12-1 EC NO: 208-221-6 Molecular Formula: C4H4INO2

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Chemistry

Molecular Structure of N-Iodosuccinimide (CAS NO.516-12-1):

IUPAC Name: 1-iodopyrrolidine-2,5-dione  
Empirical Formula: C4H4INO2 
Molecular Weight: 224.9845 
Index of Refraction: 1.653 
Surface Tension:  62.4 dyne/cm 
Density: 2.31 g/cm3 
Flash Point: 104.8 °C 
Enthalpy of Vaporization:  48.69 kJ/mol 
Boiling Point: 249.6 °C at 760 mmHg 
Vapour Pressure:  0.0227 mmHg at 25°C 
storage temp.:2-8°C
Water Solubility: decomposes
Synonyms of N-Iodosuccinimide (CAS NO.516-12-1): 1-Iodo-2,5-pyrrolidinedione ; nis;n-iodosuccinimide ; 1-iodo-5-pyrrolidinedione ; n-iodo-succinimid ; succinimide,n-iodo- ; succiniodimide ; 1-iodopyrrolidine-2,5-dione

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02815,

Safety Profile

Hazard Codes HarmfulXn,IrritantXi
Risk Statements 22-36/37/38 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.

Specification

 N-Iodosuccinimide (CAS NO.516-12-1) is a white-yellow to brown crystalline powder,be sensitive to water and ligh.In organic synthesis for ketones, aldehydes of iodide, primarily as a  pharmaceutical intermediates  in the biological drug, its production method is without light conditions, in reaction of succinimide and silver oxide, Preparation N-succinic imide silver, in dry dioxane in the reaction ti get N-iodo succinimide.