Product Name

  • Name

    N-Iodosuccinimide

  • EINECS 208-221-6
  • CAS No. 516-12-1
  • Article Data20
  • CAS DataBase
  • Density 2.31 g/cm3
  • Solubility decomposes in water
  • Melting Point 173 -175
  • Formula C4H4INO2
  • Boiling Point 249.6 °C at 760 mmHg
  • Molecular Weight 224.986
  • Flash Point 104.8 °C
  • Transport Information
  • Appearance white-yellow to brown crystalline powder
  • Safety 26-36-37/39
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 516-12-1 (N-Iodosuccinimide)
  • Hazard Symbols HarmfulXn,IrritantXi
  • 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;
  • PSA 37.38000
  • LogP 0.42330

Synthetic route

Succinimide
123-56-8

Succinimide

N-iodo-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;
N-chloro-succinimide
128-09-6

N-chloro-succinimide

N-iodo-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;
N-Bromosuccinimide
128-08-5

N-Bromosuccinimide

N-iodo-succinimide
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℃;
Succinimide
123-56-8

Succinimide

iodine
7553-56-2

iodine

acetone
67-64-1

acetone

N-iodo-succinimide
516-12-1

N-iodo-succinimide

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

mercury comp bond of succinimide

N-iodo-succinimide
516-12-1

N-iodo-succinimide

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

silver compound of succinimide

N-iodo-succinimide
516-12-1

N-iodo-succinimide

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

silver-compound of succinimide

N-iodo-succinimide
516-12-1

N-iodo-succinimide

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

N-iodo-succinimide

((C2H5)2C2B4H4)Nb(Cl)2(C5H5)
167033-03-6

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

C5H5Cl2Nb((C2H5)2C2B4H3I)
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%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

(η5-C5H5)Co(Et2C2B3H5)

(η5-C5H5)Co(Et2C2B3H5)

(C5H5)Co((C2H5)2C2B3H3I2)

(C5H5)Co((C2H5)2C2B3H3I2)

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

N-iodo-succinimide

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

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

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

(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%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

2,3-dihydro-4-hydroxybenzofuran
144822-82-2

2,3-dihydro-4-hydroxybenzofuran

5-bromo-7-iodo-2,3-dihydrobenzofuran-4-ol

5-bromo-7-iodo-2,3-dihydrobenzofuran-4-ol

Conditions
ConditionsYield
Stage #1: 4-hydroxy-2,3-dihydrobenzofuran With phosphorus tribromide In methanol
Stage #2: N-iodo-succinimide In acetonitrile		100%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

nido-(η(5)-C5Me5)Co(2,3-Et2C2B3H5)

nido-(η(5)-C5Me5)Co(2,3-Et2C2B3H5)

(C5(CH3)5)Co((CH3CH2)2C2B3H4I)

(C5(CH3)5)Co((CH3CH2)2C2B3H4I)

Conditions
ConditionsYield
In tetrahydrofuran dissoln. of Co-complex in THF, addn. of succinimide-compd., stirring in vac. for < 5 min (color change from yellow to brownish-orange); rotary evapn, soln. of residue in hexane, elution on a silica column; elem. anal.;99%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

(C5(CH3)5)Co((CH3CH2)2C2B3H4I)

(C5(CH3)5)Co((CH3CH2)2C2B3H4I)

(C5(CH3)5)Co((CH3CH2)2C2B3H3I2)

(C5(CH3)5)Co((CH3CH2)2C2B3H3I2)

Conditions
ConditionsYield
In tetrahydrofuran dissoln. of Co-complex in THF, addn. of 1.5 equiv. of succinimide-compd., stirring, (immediate color change from orange to dark orange-brown);99%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

(Et2C2B4H4)(Cp)TaCl2
162476-46-2

(Et2C2B4H4)(Cp)TaCl2

C5H5Cl2Ta((C2H5)2C2B4H3I)
266323-90-4

C5H5Cl2Ta((C2H5)2C2B4H3I)

Conditions
ConditionsYield
In tetrahydrofuran Ta-complex was dissolved in THF, ligand was added, stirred for 3 h underinert atm.; solvent was removed, residue was flash-chromd. through silica gel with CH2Cl2; elem. anal.;99%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

Cp*Co[2,3-Et2C2B4H3-7-CCSi(CH3)3]
557791-54-5

Cp*Co[2,3-Et2C2B4H3-7-CCSi(CH3)3]

[(CH3)5C5]Co[[(C2H5)2C2B4H2(C2Si(CH3)3)]I]
565471-06-9

[(CH3)5C5]Co[[(C2H5)2C2B4H2(C2Si(CH3)3)]I]

Conditions
ConditionsYield
In dichloromethane C4H4N(O)2(I) in CH2Cl2 added dropwise to Co-comp. in dry CH2Cl2 at 0°C, stirred at 0°C for 1 h, then at room temp. for 1 h; solv. removed, flash chromy in hexane, washed with CH2Cl2, solv. removed;99%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

5-phenyl-5-pentenoic acid
174708-24-8

5-phenyl-5-pentenoic acid

(R)-6-(iodomethyl)-6-phenyltetrahydro-2H-pyran-2-one
1370729-62-6

(R)-6-(iodomethyl)-6-phenyltetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With 3,3'-bis((E)-(((1R,2R)-2-(isoindolin-2-yl)-1,2-diphenylethyl)imino)methyl)-[1,1'-binaphthalene]-2,2'-diol; zinc diacetate In dichloromethane at -78℃; for 18h;99%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

(η5-C5Me5)Co(Et2C2B4H4)

(η5-C5Me5)Co(Et2C2B4H4)

(η(5)-C5Me5)Co(2,3-Et2C2B4H3-5-I)

(η(5)-C5Me5)Co(2,3-Et2C2B4H3-5-I)

Conditions
ConditionsYield
In tetrahydrofuran inert atmosphere, 1 h; evapn., chromy. (SiO2, CH2Cl2), evapn.; elem. anal.;98%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

Cs{(7,8-C2B9H11)2Fe}
12304-97-1

Cs{(7,8-C2B9H11)2Fe}

Cs[3,3’-Fe(8-I-1,2-C2B9H10)(1,2-C2B9H11)]

Cs[3,3’-Fe(8-I-1,2-C2B9H10)(1,2-C2B9H11)]

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In ethanol for 2h; Reflux;98%
In ethanol at 20℃;92%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

[3-(tert-butyldimethylsilyl)-5-methyl-4,9-dioxobicyclo[3.3.1]non-2-en-2-yl]gold[ditert-butyl(2-phenylphenyl)phosphine]

[3-(tert-butyldimethylsilyl)-5-methyl-4,9-dioxobicyclo[3.3.1]non-2-en-2-yl]gold[ditert-butyl(2-phenylphenyl)phosphine]

3-(tert-butyldimethylsilyl)-4-iodo-1-methylbicyclo[3.3.1]non-3-ene-2,9-dione

3-(tert-butyldimethylsilyl)-4-iodo-1-methylbicyclo[3.3.1]non-3-ene-2,9-dione

Conditions
ConditionsYield
In acetone at 35℃; for 24h; Sealed tube; Inert atmosphere;98%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

[5-methyl-4,9-dioxo-2-(triphenylsilyl)bicyclo[3.3.1]non-2-en-3-yl]gold[di-tertbutyl(2-phenylphenyl)phosphine]

[5-methyl-4,9-dioxo-2-(triphenylsilyl)bicyclo[3.3.1]non-2-en-3-yl]gold[di-tertbutyl(2-phenylphenyl)phosphine]

3-iodo-1-methyl-4-(triphenylsilyl)bicyclo[3.3.1]non-3-ene-2,9-dione

3-iodo-1-methyl-4-(triphenylsilyl)bicyclo[3.3.1]non-3-ene-2,9-dione

Conditions
ConditionsYield
In acetone at 35℃; for 24h; Sealed tube; Inert atmosphere;98%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

benzyl N-[(1E)-prop-1-en-1-yl]-carbamate
260967-14-4

benzyl N-[(1E)-prop-1-en-1-yl]-carbamate

A

benzyl (1-(2,5-dioxopyrrolidin-1-yl)-2-iodopropyl)carbamate

benzyl (1-(2,5-dioxopyrrolidin-1-yl)-2-iodopropyl)carbamate

B

benzyl ((1R,2S)-1-(2,5-dioxopyrrolidin-1-yl)-2-iodopropyl)carbamate

benzyl ((1R,2S)-1-(2,5-dioxopyrrolidin-1-yl)-2-iodopropyl)carbamate

C

benzyl ((1S,2R)-1-(2,5-dioxopyrrolidin-1-yl)-2-iodopropyl)carbamate

benzyl ((1S,2R)-1-(2,5-dioxopyrrolidin-1-yl)-2-iodopropyl)carbamate

Conditions
ConditionsYield
Stage #1: benzyl N-[(1E)-prop-1-en-1-yl]-carbamate With 2C48H28O4P(1-)*Ca(2+) In toluene at 20℃; for 0.0333333h; Molecular sieve; Inert atmosphere;
Stage #2: N-iodo-succinimide In toluene at 20℃; for 16h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;		A n/a
B 98%
C n/a
...Expand
N-iodo-succinimide
516-12-1

N-iodo-succinimide

Cs{(7,8-C2B9H11)2Fe}
12304-97-1

Cs{(7,8-C2B9H11)2Fe}

tetramethylammonium bromide
64-20-0

tetramethylammonium bromide

[Me4N][8,8′-I2-3,3′-Fe(1,2-C2B9H10)2]

[Me4N][8,8′-I2-3,3′-Fe(1,2-C2B9H10)2]

Conditions
ConditionsYield
Stage #1: N-iodo-succinimide; Cs{(7,8-C2B9H11)2Fe} In tetrahydrofuran at 20℃; for 0.75h;
Stage #2: tetramethylammonium bromide In water; acetone Cooling;		98%
...Expand
N-iodo-succinimide
516-12-1

N-iodo-succinimide

C26H33BF2N2O2

C26H33BF2N2O2

C26H31BF2I2N2O2

C26H31BF2I2N2O2

Conditions
ConditionsYield
In dichloromethane at 25℃;98%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

(η5-HC2C5H4)Fe(CO)2(CH3)

(η5-HC2C5H4)Fe(CO)2(CH3)

(η5-IC2C5H4)Fe(CO)2(CH3)

(η5-IC2C5H4)Fe(CO)2(CH3)

Conditions
ConditionsYield
With potassium hydroxide In methanol Ar atmosphere; cooling soln. of metal-complex in MeOH (0°C), addn. of solid KOH, stirring (low temp., 20 min), addn. of solid org. compd., stirring (15 min, 0°C), warming (room temp., 20 min); addn. of Et2O, extn. (brine), sepn. of org. layer, drying (MgSO4), filtration, evapn.;97%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

[(η6-benzene)Fe(II)(Et2C2B4H3-5-(eta.6-C6H5)Fe(II)(Et2C2B4H4)]

[(η6-benzene)Fe(II)(Et2C2B4H3-5-(eta.6-C6H5)Fe(II)(Et2C2B4H4)]

[(C6H6)Fe((C2H5)2C2B4H3-5-Ph)Fe((C2H5)2C2B4H3-5-I)]

[(C6H6)Fe((C2H5)2C2B4H3-5-Ph)Fe((C2H5)2C2B4H3-5-I)]

Conditions
ConditionsYield
In dichloromethane in air; N-iodosuccinimide was added to a cold (0°C) soln. of Fe complex in CH2Cl2, after 0.5 h the mixt. was warmed to 25°C and stirred for 1 h; the residue was chromd. (CH2Cl2);97%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

(η6-C6H6)Fe(Et2C2B4H4)
84582-99-0

(η6-C6H6)Fe(Et2C2B4H4)

(η6-C6H6)Fe(2,3-(C2H5)2C2B4H3-5-I)

(η6-C6H6)Fe(2,3-(C2H5)2C2B4H3-5-I)

Conditions
ConditionsYield
In dichloromethane in air; N-iodosuccinimide was added to a cold (0°C) soln. of Fe complex in CH2Cl2, after 0.5 h the mixt. was warmed to 25°C and stirred for 1.5 h; the mixt. was evapd., the residue was chromd. (CH2Cl2/hexanes); elem. anal.;97%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

B-ethynyl N-methyliminodiacetic acid boronate
1104637-53-7

B-ethynyl N-methyliminodiacetic acid boronate

(CH3N(CH2C(O)O)2)BCCI
1260504-82-2

(CH3N(CH2C(O)O)2)BCCI

Conditions
ConditionsYield
With AgNO3 In not given97%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

8-(2-hydroxymethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

8-(2-hydroxymethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

2,6-diiodo-8-(2-hydroxymethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

2,6-diiodo-8-(2-hydroxymethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.5h;97%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

C57H52B2F4N4O2

C57H52B2F4N4O2

C57H51B2F4IN4O2

C57H51B2F4IN4O2

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;96%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

5,5-difluoro-1,3,7,9-tetramethyl-2,10-diphenyl-5H-5λ,6λ-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine
1401615-69-7

5,5-difluoro-1,3,7,9-tetramethyl-2,10-diphenyl-5H-5λ,6λ-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

C25H22BF2IN2
1446436-21-0

C25H22BF2IN2

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;96%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

C15H8F2O2

C15H8F2O2

4,4'-(2,2-diiodoethene-1,1-diyl)bis(fluorobenzene)

4,4'-(2,2-diiodoethene-1,1-diyl)bis(fluorobenzene)

Conditions
ConditionsYield
In chlorobenzene at 160℃; for 24h; Sealed tube;96%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

1-trichloroacetimido-(2E,4E)-octadecadiene
104808-42-6

1-trichloroacetimido-(2E,4E)-octadecadiene

trans-5-iodo-4-tetradec-(1E)-en-1-yl-2-trichloromethyl-4,5-dihydro-1,3-oxazine
104808-77-7, 104874-78-4

trans-5-iodo-4-tetradec-(1E)-en-1-yl-2-trichloromethyl-4,5-dihydro-1,3-oxazine

Conditions
ConditionsYield
In chloroform for 12h; Ambient temperature;95%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

(η5-cyclopentadienyl)Co(2,3-Et2C2B4H4)

(η5-cyclopentadienyl)Co(2,3-Et2C2B4H4)

(η5-cyclopentadienyl)Co(2,3-Et2C2B4H3-5-I)
170467-45-5

(η5-cyclopentadienyl)Co(2,3-Et2C2B4H3-5-I)

Conditions
ConditionsYield
In tetrahydrofuran inert atmosphere, 1 h; evapn., chromy. (SiO2, petroleum ether / CH2Cl2 = 4 : 1); elem. anal.;95%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

((CH3)5C5)Fe(H)((C2H5)2C2B4H4)

((CH3)5C5)Fe(H)((C2H5)2C2B4H4)

(η(5)-C5Me5)Fe(2,3-Et2C2B4H3-5-I)
170467-54-6

(η(5)-C5Me5)Fe(2,3-Et2C2B4H3-5-I)

Conditions
ConditionsYield
In tetrahydrofuran inert atmosphere; stirring (4 h); evapn., chromy. (SiO2, CH2Cl2); elem. anal.;95%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

C30H31BF2N2O2

C30H31BF2N2O2

C30H30BF2IN2O2

C30H30BF2IN2O2

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 8.5h; Inert atmosphere; Reflux;95%
N-iodo-succinimide
516-12-1

N-iodo-succinimide

C26H23BF2N2O

C26H23BF2N2O

C26H22BF2IN2O
1446436-20-9

C26H22BF2IN2O

Conditions
ConditionsYield
In dichloromethane95%

N-Iodosuccinimide Chemical Properties

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

N-Iodosuccinimide 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,

N-Iodosuccinimide 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.

N-Iodosuccinimide 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.

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