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123-56-8

Basic Information
CAS No.: 123-56-8
Name: Succinimide
Molecular Structure:
Molecular Structure of 123-56-8 (Succinimide)
Formula: C4H5NO2
Molecular Weight: 99.09
Synonyms: dihydro-3-pyrroline-2,5-dione;Butanimide;2, 5-Dioxopyrrolidine;Lubrizol 6406;Succinic imide;2,4,6-Trichlorophenyl hydrazine;Succinic acid imide;pyrrolidine-2,5-dione;L 113B;2,5-dioxopyrrolidine;2,5-Pyrrolidinedione;3, 4-Dihydropyrrolidine;3,4-dihydropyrrole-2,5-dione;Succinimide-Sauba;2,5-Diketopyrrolidine;
EINECS: 204-635-6
Density: 1.274 g/cm3
Melting Point: 123-125°C
Boiling Point: 288 °C at 760 mmHg
Flash Point: 160 °C
Solubility: Soluble in water and ethanol. Insoluble in ether and chloroform.
Appearance: A white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-36-26
Transport Information:
PSA: 46.17000
LogP: -0.24820
Synthetic route
541-59-3

maleiimide

123-56-8

Succinimide

Conditions
ConditionsYield
With acetic anhydride; zinc In toluene at 40 - 86℃; for 48h; Inert atmosphere; chemoselective reaction;100%
With sulfuric acid In water for 5h; Electrochemical reaction; Flow reactor; chemoselective reaction;96%
With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;96%
110-89-4

piperidine

A

123-56-8

Succinimide

B

25116-80-7

N,N'-thiodipiperidine

C

6091-44-7

piperidine hydrochloride

Conditions
ConditionsYield
With N-chlorothiophthalimide In 1,2-dichloro-ethane at 20 - 25℃; for 2h;A n/a
B 77%
C 100%
24434-16-0

2,5-diphenyl-2,5-hexanediol

A

123-56-8

Succinimide

B

98-86-2

acetophenone

Conditions
ConditionsYield
With N-iodo-succinimide In benzene for 6h; Product distribution; Irradiation; varying reaction time;A 99%
B 100%
70289-38-2

4-Chloro-1-(4-isopropyl-phenyl)-butan-1-one

A

123-56-8

Succinimide

B

169280-04-0

1-[4-(1-Bromo-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 20 - 90℃; for 0.75h; Heating / reflux; Irradiation;A n/a
B 100%

NiCH2CH2CONH(P(C6H11)3)

A

123-56-8

Succinimide

B

18475-08-6

(tricyclohexylphosphane)Ni(0)(CO)3

Conditions
ConditionsYield
With carbon monoxide In diethyl ether N2 or Ar, stirred for 3 h; filtered; IR, NMR, GC;A 100%
B n/a
84839-03-2

dibutyldisuccinimidostannane

A

123-56-8

Succinimide

B

683-18-1

dibutyltin chloride

Conditions
ConditionsYield
With hydrogenchloride In methanol passing gaseous HCl through Sn-compd. suspn. at room temp. until ppt. dissolved; soln. evapn. to dryness at room temp., Sn-compd. isolation on residue extn. (hexane);A 100%
B 96%
616-45-5

2-pyrrolidinon

123-56-8

Succinimide

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone at 0 - 25℃; for 48h;99%
With oxygen; titanium(IV) oxide In water for 10h; Product distribution; Irradiation; other time, photocatalytic oxidations of lactams and N-acylamines;
With ruthenium(VIII)-oxide
110-03-2

2,5-dimethyl-2,5-hexanediol

A

123-56-8

Succinimide

B

67-64-1

acetone

Conditions
ConditionsYield
With N-iodo-succinimide In benzene for 0.916667h; Product distribution; Mechanism; Irradiation; varying reaction time;A 88%
B 99%
14204-24-1

N-(phenylthio)succinimide

762-04-9, 123-22-8

Diethyl phosphonate

A

123-56-8

Succinimide

B

1889-58-3

O,O-diethyl S-phenyl phosphorothioate

Conditions
ConditionsYield
In benzene for 20h; Ambient temperature;A n/a
B 99%
98-79-3

L-Pyroglutamic acid

123-56-8

Succinimide

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate In water at 20℃; for 2h; Reagent/catalyst; Temperature;99%
With iodosylbenzene In dichloromethane for 48h; Ambient temperature;27%

N-[(Z)-2-(4-methylphenylsulfonyl)ethenyl]succinimide

123-56-8

Succinimide

Conditions
ConditionsYield
With sodium hydride; 1-dodecylthiol In acetonitrile at 50℃; for 0.25h; Inert atmosphere;98%
67-56-1

methanol

65-85-0

benzoic acid

A

93-58-3

benzoic acid methyl ester

B

123-56-8

Succinimide

Conditions
ConditionsYield
With N-Bromosuccinimide at 70℃; for 20h;A 85%
B 98%
128-09-6

N-chloro-succinimide

64-17-5

ethanol

63216-04-6

2-(Benzylsulfanyl)benzonitrile

A

123-56-8

Succinimide

B

69360-26-5

2-cyanobenzenesulfonyl chloride

C

100-44-7

benzyl chloride

D

2-Cyano-benzenesulfinic acid ethyl ester

Conditions
ConditionsYield
In chloroform for 18h; Product distribution; Ambient temperature;A n/a
B n/a
C n/a
D 97%
108-30-5

succinic acid anhydride

123-56-8

Succinimide

Conditions
ConditionsYield
With dmap; hydroxylamine hydrochloride for 0.0303333h; microwave irradiation;96%
With formamide In neat (no solvent) for 0.416667h; Reagent/catalyst; Milling; Heating; Green chemistry;95%
With dmap; ammonium chloride at 150℃; for 0.0833333h; microwave irradiation;91%
110-91-8

morpholine

59939-51-4

N-(morpholinothio)imide

A

123-56-8

Succinimide

B

5038-11-9

N,N'-thiodimorpholine

Conditions
ConditionsYield
In benzene at 20 - 25℃; for 0.25h;A 96%
B 88%
14204-24-1

N-(phenylthio)succinimide

691-96-3

diisopropyl phosphite

A

123-56-8

Succinimide

B

15267-38-6

thiophosphoric acid O,O'-diisopropyl ester S-phenyl ester

Conditions
ConditionsYield
In benzene for 20h; Ambient temperature;A n/a
B 96%
149-87-1

Pyroglutamic acid

123-56-8

Succinimide

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate In water at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Time; Green chemistry;96%
128-09-6

N-chloro-succinimide

1600-27-7

mercury(II) diacetate

333-20-0

potassium thioacyanate

A

123-56-8

Succinimide

B

57-12-5

cyanide(1-)

C

16887-00-6

chloride

D

14808-79-8

Sulfate

E

hydrogen cation

Conditions
ConditionsYield
With perchloric acid In methanol; water Kinetics; oxidation of SCN(1-) by NCS in aq. methanol in presence of mercuric acetate and HClO4 (room temp.); gravimetric and iodometric methods;A n/a
B n/a
C n/a
D 94%
E n/a
With sodium hydroxide In methanol; water Kinetics; oxidation of SCN(1-) by NCS in aq. methanol in presence of mercuric acetate and NaOH at 303 K; gravimetric and iodometric methods;A n/a
B n/a
C n/a
D 94%
E n/a
128-08-5

N-Bromosuccinimide

1600-27-7

mercury(II) diacetate

333-20-0

potassium thioacyanate

A

123-56-8

Succinimide

B

506-68-3

bromocyane

C

10097-32-2

bromide

D

14808-79-8

Sulfate

E

hydrogen cation

Conditions
ConditionsYield
With sodium hydroxide In methanol; water Kinetics; oxidation of SCN(1-) by NBS in aq. methanol in presence of mercuric acetate and NaOH at 303 K; gravimetric and iodometric methods;A n/a
B 94%
C n/a
D 94%
E n/a
With perchloric acid In methanol; water Kinetics; oxidation of SCN(1-) by NBS in aq. methanol in presence of mercuric acetate and HClO4 at 273 K; gravimetric and iodometric methods;A n/a
B 94%
C n/a
D 94%
E n/a
126-81-8

dimedone

A

123-56-8

Succinimide

B

3359-52-2

bis(4,4-dimethyl-2,6-dioxo-1-cyclohexyl) sulfide

Conditions
ConditionsYield
With bis(succinimide) sulfide In 1,2-dichloro-ethane at 20 - 25℃; for 1h;A n/a
B 93%
56-84-8

L-Aspartic acid

123-56-8

Succinimide

Conditions
ConditionsYield
molecular sieve In diphenylether92.2%
With toluene-4-sulfonic acid In nitrobenzene85.5%

1-[(E)-2-(phenylsulfonyl)ethenyl]-succinimide

123-56-8

Succinimide

Conditions
ConditionsYield
With sodium hydride; 1-dodecylthiol In acetonitrile at 20℃; for 15h; Inert atmosphere;92%
trans-NiH(succinimido) (PCy3)2

trans-NiH(succinimido) (PCy3)2

123-56-8

Succinimide

Conditions
ConditionsYield
With carbon monoxide In dichloromethane for 4h; Ambient temperature;91%
82384-39-2

trans-NiH(succinimido)((C6H11)3P)2

201230-82-2

carbon monoxide

A

123-56-8

Succinimide

B

28796-12-5

(CO)2Ni(P(C6H11-cyclo)3)2

Conditions
ConditionsYield
In dichloromethane at room temp., for 4 h, with excess amount of CO;A 91%
B n/a
872-50-4

1-methyl-pyrrolidin-2-one

617-45-8

aspartic Acid

123-56-8

Succinimide

Conditions
ConditionsYield
With phosphoric acid; nitrogen; silica gel In diphenylether; acetone90.9%
617-45-8

aspartic Acid

123-56-8

Succinimide

Conditions
ConditionsYield
In diphenylether90%
In diphenylether90%
77-79-2

3-Sulfolene

{(succinimide)2silver}(silver)

A

123-56-8

Succinimide

B

2,5,2',5'-Tetrahydro-[2,2']bithiophenyl 1,1,1',1'-tetraoxide

Conditions
ConditionsYield
With nitric acid In acetonitrile Electrolysis; Electrolysis of silver salt of succinimide in CH3CN-TEABF containing sulfolene on Pt electrode at an anodic potential of 1.5 V untol zero current (45 min).; Evapn. of anolyte to dryness in vac., extn. with refluxing ether, the solid residue is treated with nitric acid and again extd. with refluxing ether.;A 90%
B n/a

1-[(Z)-2-(phenylsulfonyl)ethenyl]succinimide

123-56-8

Succinimide

Conditions
ConditionsYield
With sodium hydride; 1-dodecylthiol In acetonitrile at 20℃; for 15h; Inert atmosphere;90%
14204-24-1

N-(phenylthio)succinimide

96-36-6, 868-85-9

methyl phosphite

A

123-56-8

Succinimide

B

4237-00-7

thiophosphoric acid O,O'-dimethyl ester S-phenyl ester

Conditions
ConditionsYield
In benzene for 20h; Ambient temperature;A n/a
B 89%
110-89-4

piperidine

123-56-8

Succinimide

50-00-0

formaldehyd

13314-95-9

N-piperidinomethyl-succinimide

Conditions
ConditionsYield
With aluminum oxide In water for 0.2h; Condensation; microwave irradiation;100%
With ethanol; water
110-91-8

morpholine

123-56-8

Succinimide

50-00-0

formaldehyd

13314-97-1

N-[{morpholin-1-yl}-methyl]-pyrrolidine-2,5-dione

Conditions
ConditionsYield
With aluminum oxide In water for 0.2h; Condensation; microwave irradiation;100%
In ethanol at 60℃; for 2h;88%
123-56-8

Succinimide

75-04-7

ethylamine

3025-98-7

N-ethyl-succinic diamide

Conditions
ConditionsYield
at 20℃; under 600.048 - 750.06 Torr; Addition; soid-gas reaction; ring cleavage;100%
With water
123-56-8

Succinimide

78-94-4

methyl vinyl ketone

77356-07-1

1-(3-oxobutyl)pyrrolidine-2,5-dione

Conditions
ConditionsYield
Stage #1: Succinimide With sodium ethanolate In ethyl acetate at 20℃; for 0.25h; Inert atmosphere;
Stage #2: methyl vinyl ketone In ethyl acetate at 77℃; for 16h; Reagent/catalyst; Inert atmosphere;
100%
With poly(N-vinylimidazole) In water at 20 - 25℃; for 24h; aza-Michael reaction; Inert atmosphere;81%
With sodium ethanolate In ethyl acetate for 1h; Heating;3%
With methanol; sodium methylate
123-56-8

Succinimide

74-89-5

methylamine

3025-97-6

N-methyl-succinic diamide

Conditions
ConditionsYield
at 20℃; under 600.048 - 750.06 Torr; Addition; soid-gas reaction; ring cleavage;100%
With water
In water for 1h; Ambient temperature;
123-56-8

Succinimide

108-86-1

bromobenzene

83-25-0

N-phenylmaleimide

Conditions
ConditionsYield
With copper at 210℃; for 12h;100%
123-56-8

Succinimide

64-17-5

ethanol

39662-63-0

5-ethoxy-pyrrolidin-2-one

Conditions
ConditionsYield
With hydrogenchloride; sodium tetrahydroborate at 0℃; for 1h;100%
Stage #1: Succinimide; ethanol With sodium tetrahydroborate In ethanol at -10℃; for 0.25h; Inert atmosphere;
Stage #2: With hydrogenchloride In ethanol at -10℃; for 4h; Product distribution / selectivity; Inert atmosphere;
84%
Stage #1: Succinimide; ethanol With sodium tetrahydroborate pH=2;
Stage #2: With sulfuric acid pH=2;
81%
123-56-8

Succinimide

824-94-2

p-methoxybenzyl chloride

108640-66-0

1-[(4-methoxyphenyl)methyl]-2,5-pyrrolidinedione

Conditions
ConditionsYield
With potassium carbonate In acetonitrile100%
With potassium carbonate In acetonitrile at 25℃; for 16h;
With potassium carbonate In acetonitrile at 25℃; for 16h;
With potassium carbonate In acetonitrile at 25℃; for 16h;
123-56-8

Succinimide

124-40-3

dimethyl amine

131566-92-2

mono-N,N-dimethylamide of succinic acid

Conditions
ConditionsYield
at 20℃; under 600.048 - 750.06 Torr; Addition; soid-gas reaction; ring cleavage;100%
123-56-8

Succinimide

911395-13-6

allyl [(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(2-{4-[(2,5-dioxopyrrolidin-1-yl)methyl]phenyl}-2-oxoethyl)-4-oxoazetidin-1-yl](triphenylphosphoranilidene)acetate

Conditions
ConditionsYield
Stage #1: allyl ((2R,3S)-3-((1R)-1-{[tert-butyl-(dimethyl)-silyl]-oxy}-ethyl)-2-{2-[4-(hydroxymethyl)-phenyl]-2-oxoethyl}-4-oxoazetidin-1-yl) (triphenylphosphoranilidene) acetate With N,N-dimethyl-2-chloropropenylamine In dichloromethane at 20℃; for 0.5h;
Stage #2: Succinimide With tetrabutylammomium bromide; caesium carbonate In N,N-dimethyl-formamide for 2h;
100%
123-56-8

Succinimide

429666-52-4

3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine

1972-28-7

diethylazodicarboxylate

3-t-butyldiphenylsilyloxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; toluene100%
123-56-8

Succinimide

(C5H5)Mo(NO)(CHC(CH3)3)(C5H5N)

(C5H5)Mo(NO)(CH2C(CH3)3)(NC(O)C2H4C(O))

Conditions
ConditionsYield
In benzene-d6 air and H2O free atmosphere, NMR tube (5 min); detd. by (1)H NMR spectroscopy;100%
123-56-8

Succinimide

111033-77-3

2-[1,1'-biphenyl]-2-ylethanol

1281027-45-9

C18H17NO2

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 0 - 20℃; Mitsunobu reaction;100%
123-56-8

Succinimide

(2,2’-bipyridin-3-yl-N-oxide)palladium acetate dimer

(2,2’-bipyridin-3-yl-N-oxide)palladium succinimidate

Conditions
ConditionsYield
In acetonitrile at 40℃; for 3h;100%
123-56-8

Succinimide

5162-44-7

1-bromo-4-butene

58805-10-0

N-(3-butenyl)succinimide

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate In toluene for 16h; Heating;99.5%
Stage #1: Succinimide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: 1-bromo-4-butene In N,N-dimethyl-formamide at 50℃; for 20h;
92%
With sodium ethanolate In ethanol for 6h; Heating;
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide
Stage #1: Succinimide With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: 1-bromo-4-butene In N,N-dimethyl-formamide at 50℃; for 16h; Inert atmosphere;
130 g
123-56-8

Succinimide

18913-31-0

2,3-butadien-1-ol

92721-47-6

1-(2,3-butadienyl)-2,5-pyrrolidinedione

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 1.5h; Ambient temperature;99%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 3h;99%
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;
123-56-8

Succinimide

202462-83-7

11-[(triphenylmethyl)sulfanyl]undecanoic Acid

916980-32-0

C34H39NO4S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 5 - 20℃; for 25h;99%
123-56-8

Succinimide

50-00-0

formaldehyd

21860-03-7

2,5-di-tert-butylaniline

1182178-42-2

C19H28N2O2

Conditions
ConditionsYield
In ethanol; water Reflux;99%
In ethanol at 80℃; Inert atmosphere;89%
In ethanol; water at 80℃; Reflux;
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    Chemical Name: N-succinimide Synonyms: Succinimide;Butanimide Succinic acid imide; 2,5-Dioxopyrrolidine; 2,5-Diketopyrrolidine; 2,5-Pyrrolidinedione CAS No.: 123-56-8 Molecular Formula: C4H5NO2 Assay%≥99.0 Properties: colorless needle-

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Chemistry

Molecular Structure of Succinimide (CAS NO.123-56-8): 

IUPAC Name: pyrrolidine-2,5-dione
Empirical Formula: C4H5NO2 
Molecular Weight: 99.088 
Index of Refraction: 1.479 
Surface Tension: 43 dyne/cm 
Density: 1.274 g/cm
Flash Point: 160 °C 
Enthalpy of Vaporization: 52.72 kJ/mol 
Boiling Point: 288 °C at 760 mmHg 
Vapour Pressure: 0.0024 mmHg at 25°C 
Synonyms of Succinimide (CAS NO.123-56-8): Butanimide ; 2,5-diketopyrrolidene ; 2,5-diketopyrrolidine ; 2,5-pyrrolidinedione ; 2,5-dioxopyrrolidine ; si;succinic imide 

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 320mg/kg (320mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03763,
mouse LD50 oral 11gm/kg (11000mg/kg)   United States Patent Document. Vol. #3639606,
rat LD50 oral 14gm/kg (14000mg/kg)   Medicamentos de Actualidad. Vol. 10, Pg. 224, 1974.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes IrritantXi
Risk Statements 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 22-24/25-36-26 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes. 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Specification

 Bronopol (CAS NO.52-51-7) is a white crystalline powder,can be used as analytical reagent for the synthesis of drugs and raw materials.it derived from the reaction of succinic acid and ammonia.

 The main process is the acid and water during tung ammonia reaction to produce succinimide. Succinic acid can also be put through dropping ammonia to dissolve and react, then heated to 102 ℃ steam to water, further vacuum distillation, when heated to 180 ℃, started to collect fraction succinimide , that was finished.

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