123-56-8

Basic information

• Product Name: Succinimide
• Synonyms: 3,4-Dihydropyrrole-2,5-dione;3,4-dihydropyrrolidine;Dihydro-3-pyrroline-2,5-dione;Lubrizol 2153;Lubrizol 6406;Orotric;Pyrrolidine-2,5-dione;Succinimide-Sauba
• CAS NO: 123-56-8
• Molecular Formula: C₄H₅NO₂
• Molecular Weight: 99.09
• EINECS: 204-635-6
• Product Categories: Miscellaneous
• Mol File: 123-56-8.mol
• Article Data: 225

Chemical Properties

• Melting Point: 123-125 °C(lit.)
• Boiling Point: 285-290 °C(lit.)
• Flash Point: 201 °C
• Appearance: Off-white to beige to light brown/Powder or Flakes
• Density: 1.41
• Vapor Pressure: 0.0024mmHg at 25°C
• Refractive Index: 1.4166 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 330g/l
• PKA: 9.6(at 25℃)
• Water Solubility: Soluble in water and ethanol. Insoluble in ether and chloroform.
• Merck: 14,8871
• BRN: 108440
• CAS DataBase Reference: Succinimide(CAS DataBase Reference)
• NIST Chemistry Reference: Succinimide(123-56-8)
• EPA Substance Registry System: Succinimide(123-56-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26-S24/25
• WGK Germany: 2
• RTECS: WN2200000
• TSCA: Yes
• Hazardous Substances Data: 123-56-8(Hazardous Substances Data)

Usage

Chemical Description

Succinimide is a chemical that is mentioned briefly in the article as a contaminant in the crude product.

Description

Succinimide is a natural product found in Xanthium strumarium and Panax notoginseng with data available.Succinimide is a colorless acicular crystal or thin solid with light brown luster. It tastes sweet. Easily soluble in water, alcohol or sodium hydroxide solution, insoluble in ether, chloroform, etc. Succinimide dispersants appear as dark or brown-colored liquids with a thickness or viscosity similar to heavy syrup. They have little or no solubility in water, and because they are denser than water, will sink in a water environment. They are readily soluble in oil and lighter weight hydrocarbons, such as gasoline. Succinimide dispersants have very low vapor pressure and little noticeable odor at ambient temperatures.

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 123-56-8 differently. You can refer to the following data:
1. Succinimide is a cycle imide of succinic acid that is present in numerous biologically active compounds including anticonvulsants, antitremor, anti-Parkinson's agents.Succinimide is the key intermediate for deamidation of asparagine (Asn) and isom-erization of aspartic acid (Asp) residues in a protein or peptide, either in vivo or invitro (Wakankar and Borchardt 2006). Formation of succinimide is the rate-deter-mining step in these reactions.
2. Succinimide is used in organic syntheses and in industrial silver plating processes. It is a reagent that is used in the synthesis of Lumiflavin (L473900), which is a toxic photolysis product of vitamin B2 (R415000). Further, it is used to form covalent bonds between proteins, peptides and plastics. In addition to this, it is used as an important raw material for the synthesis of heterocyclic compounds through N-acyliminium cyclizations.

Preparation

To a flask equipped with a dropping funnel, mechanical stirrer, and a 40 cm long side arm of not less than 10 mm inside diameter is added 236 gm (2.0 mole) of succinic acid. The flask is cooled and 270 ml (4.0 moles) of 28% aqueous ammonia is slowly added with stirring. The flask is rapidly heated with an oil bath until 200 ml of water distils. The temperature of the bath is rapidly raised to 275°C. Succinimide starts to distil over the range 275-289°C, to afford 168 gm of crude product which solidifies on cooling. The intermediate fraction, boiling between 102° and 275°C, is redistilled to afford 10.0 gm of crude succinimide, b.p. 275-289°C. The combined product (178 gm) is added to 178 gm of hot ethanol. The solution is cooled, the crystals filtered, washed with 25 ml of cold ethanol, and dried to afford 163-164 gm (82-83%), m.p. 123-125°C. Approximately 4-5 gm of additional product may be obtained by concen-trating the mother liquor. Recent Japanese patents suggested inert aprotic solvents such as cyclic amides (e.g., N-methylpyrrolidone, N-acetyl-2-pyrrolidone, DMF, or tet-ramethylurea) and azeotroping solvents (e.g., toluene, 0-xylene, hexane, or pentane) or other high-boiling solvents (e.g., chlorobenzene or chlo-rotoluene) as dehydrating agents for the formation of imides from di-basic acids (e.g., 3- and/or 4) hydroxyphthalic acid with a large variety of diamines including diaminosiloxanes such as bis (3-aminopropyl)-tetra-methylsiloxane.

Definition

ChEBI: Succinimide is a dicarboximide that is pyrrolidine which is substituted by oxo groups at positions 2 and 5. It is a pyrrolidinone and a dicarboximide.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 7448, 1980 DOI: 10.1021/ja00545a009Organic Syntheses, Coll. Vol. 2, p. 562, 1943

Flammability and Explosibility

Nonflammable

Synthesis

Succinimide is obtained by the reaction of succinic acid with ammonia. Succinic acid and water are added into the reaction pot, and succinimide can be produced by ammonia reaction. Succinic acid can also be put into the reaction pot, drop ammonia, stir to dissolve and react, heat it to 102 ℃, evaporate the water, and then carry out vacuum distillation. When the temperature rises to 180 ℃, start collecting succinimide fraction to obtain the finished product.

Purification Methods

Crystallise the imide from EtOH (1mL/g) or water. [Beilstein 21 H 369, 21/9 V 438.]

InChI:InChI=1/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)

Synthetic route

maleiimide (541-59-3) → Succinimide (123-56-8)

Conditions	Yield
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%

piperidine (110-89-4) → Succinimide (123-56-8) + N,N'-thiodipiperidine (25116-80-7) + piperidine hydrochloride (6091-44-7)

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

2,5-diphenyl-2,5-hexanediol (24434-16-0) → Succinimide (123-56-8) + acetophenone (98-86-2)

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

4-Chloro-1-(4-isopropyl-phenyl)-butan-1-one (70289-38-2) → Succinimide (123-56-8) + 1-[4-(1-Bromo-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one (169280-04-0)

Conditions	Yield
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) → Succinimide (123-56-8) + (tricyclohexylphosphane)Ni(0)(CO)3 (18475-08-6)

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

dibutyldisuccinimidostannane (84839-03-2) → Succinimide (123-56-8) + dibutyltin chloride (683-18-1)

Conditions	Yield
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%

2-pyrrolidinon (616-45-5) → Succinimide (123-56-8)

Conditions	Yield
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

2,5-dimethyl-2,5-hexanediol (110-03-2) → Succinimide (123-56-8) + acetone (67-64-1)

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

N-(phenylthio)succinimide (14204-24-1) + Diethyl phosphonate (762-04-9, 123-22-8) → Succinimide (123-56-8) + O,O-diethyl S-phenyl phosphorothioate (1889-58-3)

Conditions	Yield
In benzene for 20h; Ambient temperature;	A n/a B 99%

L-Pyroglutamic acid (98-79-3) → Succinimide (123-56-8)

Conditions	Yield
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 → Succinimide (123-56-8)

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

methanol (67-56-1) + benzoic acid (65-85-0) → benzoic acid methyl ester (93-58-3) + Succinimide (123-56-8)

Conditions	Yield
With N-Bromosuccinimide at 70℃; for 20h;	A 85% B 98%

N-chloro-succinimide (128-09-6) + ethanol (64-17-5) + 2-(Benzylsulfanyl)benzonitrile (63216-04-6) → Succinimide (123-56-8) + 2-cyanobenzenesulfonyl chloride (69360-26-5) + benzyl chloride (100-44-7) + 2-Cyano-benzenesulfinic acid ethyl ester

Conditions	Yield
In chloroform for 18h; Product distribution; Ambient temperature;	A n/a B n/a C n/a D 97%

succinic acid anhydride (108-30-5) → Succinimide (123-56-8)

Conditions	Yield
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%

morpholine (110-91-8) + N-(morpholinothio)imide (59939-51-4) → Succinimide (123-56-8) + N,N'-thiodimorpholine (5038-11-9)

Conditions	Yield
In benzene at 20 - 25℃; for 0.25h;	A 96% B 88%

N-(phenylthio)succinimide (14204-24-1) + diisopropyl phosphite (691-96-3) → Succinimide (123-56-8) + thiophosphoric acid O,O'-diisopropyl ester S-phenyl ester (15267-38-6)

Conditions	Yield
In benzene for 20h; Ambient temperature;	A n/a B 96%

Pyroglutamic acid (149-87-1) → Succinimide (123-56-8)

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

N-chloro-succinimide (128-09-6) + mercury(II) diacetate (1600-27-7) + potassium thioacyanate (333-20-0) → Succinimide (123-56-8) + cyanide(1-) (57-12-5) + chloride (16887-00-6) + Sulfate (14808-79-8) + hydrogen cation

Conditions	Yield
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

N-Bromosuccinimide (128-08-5) + mercury(II) diacetate (1600-27-7) + potassium thioacyanate (333-20-0) → Succinimide (123-56-8) + bromocyane (506-68-3) + bromide (10097-32-2) + Sulfate (14808-79-8) + hydrogen cation

Conditions	Yield
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

dimedone (126-81-8) → Succinimide (123-56-8) + bis(4,4-dimethyl-2,6-dioxo-1-cyclohexyl) sulfide (3359-52-2)

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

L-Aspartic acid (56-84-8) → Succinimide (123-56-8)

Conditions	Yield
molecular sieve In diphenylether	92.2%
With toluene-4-sulfonic acid In nitrobenzene	85.5%

1-[(E)-2-(phenylsulfonyl)ethenyl]-succinimide → Succinimide (123-56-8)

Conditions	Yield
With sodium hydride; 1-dodecylthiol In acetonitrile at 20℃; for 15h; Inert atmosphere;	92%

trans-NiH(succinimido) (PCy3)2 → Succinimide (123-56-8)

Conditions	Yield
With carbon monoxide In dichloromethane for 4h; Ambient temperature;	91%

trans-NiH(succinimido)((C6H11)3P)2 (82384-39-2) + carbon monoxide (201230-82-2) → Succinimide (123-56-8) + (CO)2Ni(P(C6H11-cyclo)3)2 (28796-12-5)

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

1-methyl-pyrrolidin-2-one (872-50-4) + aspartic Acid (617-45-8) → Succinimide (123-56-8)

Conditions	Yield
With phosphoric acid; nitrogen; silica gel In diphenylether; acetone	90.9%

aspartic Acid (617-45-8) → Succinimide (123-56-8)

Conditions	Yield
In diphenylether	90%
In diphenylether	90%

3-Sulfolene (77-79-2) + {(succinimide)2silver}(silver) → Succinimide (123-56-8) + 2,5,2',5'-Tetrahydro-[2,2']bithiophenyl 1,1,1',1'-tetraoxide

Conditions	Yield
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 → Succinimide (123-56-8)

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

N-(phenylthio)succinimide (14204-24-1) + methyl phosphite (96-36-6, 868-85-9) → Succinimide (123-56-8) + thiophosphoric acid O,O'-dimethyl ester S-phenyl ester (4237-00-7)

Conditions	Yield
In benzene for 20h; Ambient temperature;	A n/a B 89%

piperidine (110-89-4) + Succinimide (123-56-8) + formaldehyd (50-00-0) → N-piperidinomethyl-succinimide (13314-95-9)

Conditions	Yield
With aluminum oxide In water for 0.2h; Condensation; microwave irradiation;	100%
With ethanol; water

morpholine (110-91-8) + Succinimide (123-56-8) + formaldehyd (50-00-0) → N-[{morpholin-1-yl}-methyl]-pyrrolidine-2,5-dione (13314-97-1)

Conditions	Yield
With aluminum oxide In water for 0.2h; Condensation; microwave irradiation;	100%
In ethanol at 60℃; for 2h;	88%

Succinimide (123-56-8) + ethylamine (75-04-7) → N-ethyl-succinic diamide (3025-98-7)

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

Succinimide (123-56-8) + methyl vinyl ketone (78-94-4) → 1-(3-oxobutyl)pyrrolidine-2,5-dione (77356-07-1)

Conditions	Yield
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

Succinimide (123-56-8) + methylamine (74-89-5) → N-methyl-succinic diamide (3025-97-6)

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

Succinimide (123-56-8) + bromobenzene (108-86-1) → N-phenylmaleimide (83-25-0)

Conditions	Yield
With copper at 210℃; for 12h;	100%

Succinimide (123-56-8) + ethanol (64-17-5) → 5-ethoxy-pyrrolidin-2-one (39662-63-0)

Conditions	Yield
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%

Succinimide (123-56-8) + p-methoxybenzyl chloride (824-94-2) → 1-[(4-methoxyphenyl)methyl]-2,5-pyrrolidinedione (108640-66-0)

Conditions	Yield
With potassium carbonate In acetonitrile	100%
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;

Succinimide (123-56-8) + dimethyl amine (124-40-3) → mono-N,N-dimethylamide of succinic acid (131566-92-2)

Conditions	Yield
at 20℃; under 600.048 - 750.06 Torr; Addition; soid-gas reaction; ring cleavage;	100%

Succinimide (123-56-8) → 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 (911395-13-6)

Conditions	Yield
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%

Succinimide (123-56-8) + 3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine (429666-52-4) + diethylazodicarboxylate (1972-28-7) → 3-t-butyldiphenylsilyloxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; toluene	100%

Succinimide (123-56-8) + (C5H5)Mo(NO)(CHC(CH3)3)(C5H5N) → (C5H5)Mo(NO)(CH2C(CH3)3)(NC(O)C2H4C(O))

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

Succinimide (123-56-8) + 2-[1,1'-biphenyl]-2-ylethanol (111033-77-3) → C18H17NO2 (1281027-45-9)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 0 - 20℃; Mitsunobu reaction;	100%

Succinimide (123-56-8) + (2,2’-bipyridin-3-yl-N-oxide)palladium acetate dimer → (2,2’-bipyridin-3-yl-N-oxide)palladium succinimidate

Conditions	Yield
In acetonitrile at 40℃; for 3h;	100%

Succinimide (123-56-8) + 1-bromo-4-butene (5162-44-7) → N-(3-butenyl)succinimide (58805-10-0)

Conditions	Yield
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

Succinimide (123-56-8) + 2,3-butadien-1-ol (18913-31-0) → 1-(2,3-butadienyl)-2,5-pyrrolidinedione (92721-47-6)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 1.5h; Ambient temperature;	99%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 3h;	99%

Succinimide (123-56-8) → N-iodo-succinimide (516-12-1)

Conditions	Yield
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;

Succinimide (123-56-8) + 11-[(triphenylmethyl)sulfanyl]undecanoic Acid (202462-83-7) → C34H39NO4S (916980-32-0)

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

Succinimide (123-56-8) + formaldehyd (50-00-0) + 2,5-di-tert-butylaniline (21860-03-7) → C19H28N2O2 (1182178-42-2)

Conditions	Yield
In ethanol; water Reflux;	99%
In ethanol at 80℃; Inert atmosphere;	89%
In ethanol; water at 80℃; Reflux;

Upstream product

• 616-45-5 2-pyrrolidinon 
• 541-59-3 maleiimide 
• 110-61-2 butanedinitrile 
• 110-15-6 succinic acid 
• 6158-14-1 (5E)-5-(hydroxyimino)pyrrolidin-2-one 
• 128-09-6 N-chloro-succinimide 
• 108-88-3 toluene 
• 67-56-1 methanol 
• 128-08-5 N-Bromosuccinimide 
• 124-41-4 sodium methylate 
• 141-52-6 sodium ethanolate 
• 109-97-7 pyrrole 
• 5146-68-9 N-(Hydroxymethyl)succinimide 
• 5626-51-7 2,5-dioxo-pyrrolidine-1-carboxylic acid amide 

Downstream Products

• 13314-97-1 N-Morpholinomethyl-succinimid 
• 6319-54-6 1-(9H-xanthen-9-yl)pyrrolidine-2,5-dione 
• 93185-45-6 4-(2-succinimidoethyl)pyridine 
• 18190-44-8 1-(2-Hydroxy-ethyl)-pyrrolidine-2,5-dione 
• 13314-95-9 N-Piperidinomethyl-succinimid 
• 63853-74-7 5-methoxypyrrolidin-2-one 
• 58805-10-0 N-(3-butenyl)succinimide 
• 116445-61-5 1-(3-chloropropyl)pyrrolidine-2,6-dione 
• 83095-06-1 N-(1,2,3,4-tetrahydroisoquinolin-2-ylmethyl)succinimide 
• 120572-14-7 N-[(E)-1-[3-(2,5-Dioxo-pyrrolidin-1-ylmethyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-2-(3-nitro-phenyl)-vinyl]-benzamide 
• 139221-86-6 N-[(Z)-1-[6,8-Dibromo-3-(2,5-dioxo-pyrrolidin-1-ylmethyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-2-(4-methoxy-phenyl)-vinyl]-benzamide 
• 83-25-0 N-phenylmaleimide 
• 74731-86-5 1-(4-Phenyl-[1,3]dithiol-2-yl)-pyrrolidine-2,5-dione 
• 74731-85-4 1-(4,5-Diphenyl-[1,3]dithiol-2-yl)-pyrrolidine-2,5-dione 

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Characterization of Succinimide (cas 123-56-8) stability during trypsin digestion for LC-MS analysis09/26/2019

LC-MS peptide mapping is the most commonly used method to analyze protein modifications. The proteins are generally digested using trypsin at a slightly basic pH at 37 °C from several hours to overnight. Assay-induced artifacts can be generated during this procedure, potentially causing false-p...detailed

Synthesis, antimicrobial activity and quantum chemical investigation of novel Succinimide (cas 123-56-8) derivatives09/24/2019

In the present study, twelve new 1-aryl-3-ethyl-3-methylpyrrolidine-2,5-diones were synthesized and their structures were characterized by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. In the final step of synthetic rout, condensation between corresponding succinic acid and substit...detailed

Research ArticlePharmaceutical BiotechnologyCharacterization of Ring-Opening Reaction of Succinimide (cas 123-56-8) Linkers in ADCs09/10/2019

A new class of highly potent biopharmaceutical drugs, antibody-drug conjugates (ADCs), has been proven to be clinically effective to treat oncologic diseases. ADCs contain 3 major components: the monoclonal antibody, cytotoxic drug, and chemical linker. THIOMAB™ drug conjugates and interchain-cy...detailed

Characterization and quantification of Succinimide (cas 123-56-8) using peptide mapping under low-pH conditions and hydrophobic interaction chromatography09/09/2019

Characterization of asparagine deamidation and aspartic acid isomerization is an important aspect of biotherapeutic protein analysis due to the potential negative effect of these modifications on drug efficacy and stability. Succinimide has long been known to be an intermediate product of aspara...detailed

General CommentaryAn Automated and Qualified Platform Method for Site-Specific Succinimide (cas 123-56-8) and Deamidation Quantitation Using Low-pH Peptide Mapping09/08/2019

ABSTRACTMonoclonal antibodies undergo several post-translational modifications, including the formation of succinimide from the deamidation of asparagine or the isomerization of aspartic acid. Because of the potential impact of succinimide formation on the biological activity of monoclonal antib...detailed

Relevant articles and documents

Unexpected Hydrogenation of C-C-Double Bonds with tert-Butyl Iodide

Heating of 3-isobutylidene-2,5-diketopiperazines 1 or 4, maleinimide or 2,3-dichloro-5,6-dicyano-p-benzoquinone with tert-butyl iodide in toluene gave rise to hydrogenation of the conjugated C-C-double bond affording 3-isobutyldiketopiperazines 2(rac) and 3(rac), succinimide, or 2,3-dichloro-5,6-dicyanohydroquinone, respectively. Furthermore, an interesting N-O-migration of a benzoyl group as well as reductive aromatization to pyrazines 5 and 6, respectively, were observed.

Two-Bond Cleavage in the Oxidation of Acyclic Tertiary 1,4-Diols with N-Iodosuccinimide

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Synthesis, characterization and cytotoxic studies of novel 1,2,4-triazole-azomethine conjugates

Abstract: A series of 1,2,4-triazole-schiff hybrids were synthesized and characterized by mass spectrometry, FTIR and NMR spectroscopy. The compounds were screened for anticancer activity against human breast cancer cell line (MCF-7 and T47D) and human cervical cancer cell line (HeLa). The result indicates that newly synthesized compounds exhibit cytotoxicity to all cell lines studied. In particular, MCF-7 cells were shown to be more sensitive with EC50 50 13.10?μM/ml. To further investigate the mode of cell death, early and late apoptosis studies were done on MCF-7 cells. The externalization of phosphatidylserine and DNA fragmentation supports the apoptosis as the major mode of cell death induced by derivatives on MCF-7 cells. Graphic abstract: [Figure not available: see fulltext.]

One-Electron Reduction Potential and Ring Opening of the Succinimidyl Radical in Water

By means of pulse radiolysis in water, N-chlorosuccinimide (SCl) was reduced in a one-electron step to yield the succinimidyl radicals, S*, via the intermediacy of the radical anion, SCl*-.The rate of ring opening of S* was measured to be 8 x 104 s-1.By equilibrium with Cl2*-/2Cl-, the one-electron reduction potential of S* was determined to be 2.22 +/- 0.02 V vs NHE.From this value and other data, the N-H bond strength in succinimide was calculated to be 118 +/- 3 kcal/mol.

Polarographic determination of vitamin C after derivatization with o-phenylenediamine

A differential pulse polarographic (DPP) method has been developed for the determination of ascorbic acid (AA) and dehydroascorbic acid (DHA), the two main forms of Vitamin C. The method consists of the DPP analysis of a quinoxaline obtained by the derivatization of DHA with o-phenylenediamine. Results using the proposed method correlated well with those obtained by two reference methodologies: the common iodometric method and a published chromatographic methodology. It was also used in the study of Vitamin C degradation in fruit juices, showing that it involves an initial oxidation of AA to DHA, followed by ydrolytic degradation of the latter.

Mechanism of Photoredox-Initiated C-C and C-N Bond Formation by Arylation of IPrAu(I)-CF3 and IPrAu(I)-Succinimide

Herein, we report on the photoredox-initiated gold-mediated C(sp2)-CF3 and C(sp2)-N coupling reactions. By adopting gold as a platform for probing metallaphotoredox catalysis, we demonstrate that cationic gold(III) complexes are the key intermediates of the C-C and C-N coupling reactions. The high-valent gold(III) intermediates are accessed by virtue of photoredox catalysis through a radical chain process. In addition, the bond-forming step of the coupling reactions is the reductive elimination from cationic gold(III) intermediates, which is supported by isolation and crystallographic characterization of key Au(III) intermediates.

Synthesis of biobased succinimide from glutamic acid via silver-catalyzed decarboxylation

Glutamic acid was transformed into succinimide in a two step procedure involving a dehydration in water to pyroglutamic acid followed by an oxidative decarboxylation using a silver catalyst.

Reply to the Correspondence on “Preorganization and Cooperation for Highly Efficient and Reversible Capture of Low-Concentration CO2 by Ionic Liquids”

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N -Iodosuccinimide-Promoted Selective Construction of Cyclopropyl and Dihydrofuranyl Spirooxindoles from Alkylidene Oxindoles and Annular β-Dicarbonyl Compounds

An efficient N-iodosuccinimide-promoted cyclization of readily available alkylidene oxindoles with annular β-dicarbonyl compounds has been demonstrated. With five-membered cyclic β-dicarbonyl compounds as the starting materials, a series of cyclopropyl oxindoles can be obtained in good to excellent yields, whereas the method affords dihydrofuranyl spirooxindoles almost quantitatively when six- or seven-membered cyclic β-dicarbonyl compounds are employed. This protocol provides a new alternative to the practical synthesis of structurally diverse spirooxindoles.

Method for preparing diloxitol fumarate

The invention relates to the technical field of a bulk drug preparation method and in particular relates to a method for preparing a bulk drug diloxitol fumarate. The preparation method comprises thefollowing steps: 1) performing an ammoniation reaction, namely enabling succinic anhydride to react with an ammoniating reagent so as to produce succinimide; 2) performing an alkylation reaction, namely enabling succinimide to react with 1,2 halogenated ethane in the presence of a catalyst and a base so as to generate a compound of a formula IV shown in the description; and 3) performing an esterification reaction, namely enabling a compound of a formula IV compound shown in the description to react with trans-monomethyl fumarate, so as to generate diloxifyl fumarate. The method has the advantages that material reagents used in the method are convenient and easy to obtain, the reaction steps are short, the total yield is high, the product is easy to purify through recrystallization, and base toxic impurities are easy to be controlled through recrystallization, and the like.