PRODUCTS

SUCCINIMIDE

Succinimide is a versatile cyclic imide widely used as an intermediate in pharmaceutical, agrochemical, and specialty chemical synthesis.
Succinimide's compact five-membered imide structure provides useful reactivity for producing N-substituted derivatives and other nitrogen-containing compounds.
With broad applicability in fine chemical manufacturing and research, succinimide serves as a reliable building block for controlled organic synthesis.

CAS Number: 123-56-8
EC Number: 204-635-6
Molecular Formula: C4H5NO2
Molecular Weight: 99.09 g/mol

Synonyms: SUCCINIMIDE, 123-56-8, pyrrolidine-2,5-dione, 2,5-Pyrrolidinedione, Butanimide, 2,5-Dioxopyrrolidine, Succinic acid imide, 2,5-Diketopyrrolidine, Succinic imide, 3,4-Dihydropyrrole-2,5-dione, Dihydro-3-pyrroline-2,5-dione, DTXSID8051629, NSC-11204, CHEBI:9307, 10X90O3503, DTXCID3030181, RefChem:6266, 204-635-6, 679-911-6, Succinimide-sauba, 3,4-Dihydropyrrolidine, MFCD00005495, NSC 11204, SUCCIMIDE, Letrozole Impurity 22, azolidine-2,5-dione, Mercury, disuccinimido-, WLN: T5VMVTJ, 2, mercury(2+) salt, Succinimide, mercury(2+) salt, EINECS 204-635-6, BRN 0108440, succinimid, cis-succinimide, AI3-08539, UNII-10X90O3503, 2,5dioxopyrrolidine, Lubrizol 6406, pyrroldine-2,5-dione, SUCCINIMIDE [MI], SCHEMBL774, EC 204-635-6, SUCCINIMIDE [MART.], SCHEMBL18634, SUCCINIMIDE [WHO-DD], 5-21-09-00438 (Beilstein Handbook Reference), SCHEMBL867714, BDBM7814, CHEMBL275661, orb3029565, SCHEMBL1466558, SCHEMBL1600526, SCHEMBL3675094, SCHEMBL10203348, SCHEMBL11190350, PDK0050, NSC11204, NSC13114, NSC38417, NSC41221, NSC49152, Tox21_303851, EBC-04371, NSC-13114, NSC-49152, SBB040866, STL163344, AKOS000118776, DB13376, NCGC00357119-01, BP-21153, CAS-123-56-8, HY-41877, CS-0019112, NS00001653, ST50214456, EN300-17963, C07273, D08532, F358203, Q419430, Z57127349, F1908-0169, 1BBF5533-77F1-4B20-96F3-0BB022C36CD3, InChI=1/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7, 25950-42-9, 108440, 123-56-8, 2,5-Pyrrolidindion, 2,5-Pyrrolidinedione, 2,5-Pyrrolidinedione, 204-635-6, pyrrolidine-2,5-dione, succinic acid imide, Succinimide, 2,5-Diketopyrrolidine, 2,5-dioxo-Pyrrolidine, 2,5-Dioxopyrrolidine, 204-635-6MFCD00005495, 3,4-didehydropyrrole-2,5-dione, 3,4-didehydropyrrole-2,5-quinone, 3,4-dihydropyrrole-2,5-dione, 3,4-Dihydropyrrolidine, 4-(1-cyclohexenyl)morpholin-4-ium, 4-(cyclohexen-1-yl)morpholin-4-ium, 5-21-09-00438, 98%, [τ protein] kinase, A4TVL0_9PROT, azolidine-2,5-dione, barnsteenzuurimide, Cereblon isoform 4, CRBN_HUMAN, dihydro-3-pyrroline-2,5-dione, G1T8E2_RABIT, Glycogen synthase kinase-3 beta [7-25], Protein cereblon, Pyrrolidin-2,5-dion, pyrrolidine-2,5-dione, succimide, succinimida, Succinimide pharbiol, Succinimide-sauba, T5VMVTJ

Succinimide is an organic compound with the formula (CH2)2(CO)2NH.
Succinimide is used in a variety of organic syntheses, as well as in some industrial silver plating processes.

Succinimide is classified as a cyclic imide.
Succinimide may be prepared by thermal decomposition of ammonium succinate.

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

Succinimide is used in organic syntheses and in industrial silver plating processes.
Succinimide is also used as anticonvulsant drugs such as ethosuximide, phensuximide and methsuximide.

Further, Succinimide is used to form covalent bonds between proteins, peptides and plastics.
In addition to this, Succinimide is used as an important raw material for the synthesis of heterocyclic compounds through N-acyliminium cyclizations.

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.

Succinimide tastes sweet.
Succinimide is 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.

Succinimide is a cyclic imide compound derived from succinic acid, with the molecular formula C4H5NO2.
Succinimide typically appears as a white crystalline solid and contains a five-membered ring with two carbonyl groups adjacent to a nitrogen atom.

Succinimide is widely used as an intermediate in pharmaceutical synthesis, agrochemicals, specialty chemicals, and the preparation of N-substituted succinimide derivatives.
Succinimide's imide functionality provides useful reactivity for organic synthesis, making it an important building block in nitrogen-containing compounds and functional materials.

Succinimide is a versatile cyclic imide that plays a crucial role in various industrial and research applications.
Known for its stability and low toxicity, Succinimide serves as a key intermediate in the synthesis of pharmaceuticals, agrochemicals, and polymers.

Succinimide's unique structure allows for the formation of derivatives that can enhance the properties of end products, making it valuable in drug development and material science.
Researchers often utilize succinimide in peptide synthesis and as a reagent in organic reactions, where it can facilitate the formation of amides and other functional groups.

In addition to Succinimide's applications in the pharmaceutical industry, succinimide is also employed in the production of high-performance coatings and adhesives, where its thermal stability and chemical resistance are advantageous.
Succinimide's ability to act as a solvent and stabilizer further expands its utility in various formulations.
With its proven track record and diverse applications, succinimide is an essential compound for professionals seeking reliable and effective solutions in their projects.

Succinimide, with the CAS number 123-56-8, is a cyclic imide derived from succinic acid.
Succinimide appears as a white crystalline solid and is soluble in polar solvents such as water, alcohols, and acetone.

Succinimide has a molecular formula of C4H5NO2 and a molecular weight of approximately 99.09 g/mol.
Succinimide is characterized by its stable structure, which features a five-membered ring containing both carbonyl and nitrogen functional groups.

Succinimide is primarily used in organic synthesis and as an intermediate in the production of pharmaceuticals, agrochemicals, and other chemical compounds.
Succinimide also serves as a reagent in various chemical reactions, including the synthesis of other imides and amides.

Succinimides:
Succinimides refers to compounds that contain the succinimide group.
These compounds have some notable uses.
Several succinimides are used as anticonvulsant drugs, including ethosuximide, phensuximide, and methsuximide.

Succinimides are also used to form covalent bonds between proteins or peptides and plastics, which is useful in a variety of assay techniques.

Uses of Succinimide:
Succinimide is used in organic syntheses and in industrial silver plating processes.
Succinimide is a reagent that is used in the synthesis of Lumiflavin (L473900), which is a toxic photolysis product of vitamin B2 (R415000).

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.

Succinimide is used in organic syntheses and in industrial silver plating processes.
Succinimide is also used as anticonvulsant drugs such as ethosuximide, phensuximide and methsuximide.

Succinimide is widely used as an intermediate in the synthesis of pharmaceuticals and other biologically active compounds.
Succinimide is used in the production of N-substituted succinimide derivatives for specialty chemical applications.

Succinimide serves as a building block in organic synthesis for introducing imide and nitrogen-containing functional groups.
Succinimide derivatives are used in agrochemical research and the preparation of selected crop-protection intermediates.

Succinimide is also used in polymer chemistry and functional material development as a precursor for modified imide compounds.
Succinimide can be employed in laboratory research, fine chemical synthesis, and the manufacture of specialty intermediates requiring controlled nitrogen functionality.

Preparation of Succinimide:
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 concentrating 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 dibasic acids (e.g., 3- and/or 4) hydroxyphthalic acid with a large variety of diamines including diaminosiloxanes such as bis (3-aminopropyl)-tetra-methylsiloxane.

Synthesis of Succinimide:
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.

Stability and Reactivity of Succinimide:

Chemical stability:
Succinimide is stable under normal conditions of handling and storage.

Conditions to avoid:
Avoid dust formation, excessive heat, and contact with incompatible materials.

Incompatible materials:
Avoid acids, bases, strong oxidizing agents, and strong reducing agents.

Hazardous decomposition products:
Thermal decomposition or combustion may produce nitrogen oxides, carbon monoxide, and carbon dioxide.

Handling and Storage of Succinimide:

Safe handling:
Avoid contact with skin and eyes, prevent inhalation of dust, and use adequate ventilation during handling.

Storage conditions:
Keep the container tightly closed in a cool, dry, and well-ventilated place away from incompatible materials.

First Aid Measures of Succinimide:

Inhalation:
Move the affected person to fresh air and obtain medical attention if symptoms occur.

Skin contact:
Wash thoroughly with soap and plenty of water and remove contaminated clothing.

Eye contact:
Rinse immediately with plenty of water for at least 15 minutes and obtain medical attention if irritation persists.

Ingestion:
Rinse the mouth with water and obtain medical attention.

Firefighting Measures of Succinimide:

Suitable extinguishing media:
Use water spray, carbon dioxide, dry chemical, or chemical foam.

Protective equipment:
Firefighters should wear full protective equipment and self-contained breathing apparatus.

Hazardous combustion products:
Combustion may generate nitrogen oxides, carbon monoxide, and carbon dioxide.

Accidental Release Measures of Succinimide:

Personal precautions:
Ensure adequate ventilation, avoid dust formation, and wear appropriate personal protective equipment.

Cleanup methods:
Carefully sweep or collect spilled material into suitable containers for disposal and prevent release to the environment.

Exposure Controls/Personal Protection of Succinimide:

Engineering controls:
Provide adequate ventilation, particularly in enclosed working areas.

Eye protection:
Wear appropriate safety glasses or chemical protective goggles.

Hand protection:
Wear suitable protective gloves.

Body protection:
Use appropriate protective clothing to minimize skin exposure.

Respiratory protection:
Respiratory protection is generally not required under normal conditions with adequate ventilation; use suitable particulate protection when significant dust is generated.

Identifiers of Succinimide:
Empirical Formula (Hill Notation): C4H5NO2
CAS Number: 123-56-8
Molecular Weight: 99.09
NACRES: NA.26
PubChem Substance ID: 24899836
UNSPSC Code: 12352209
EC Number: 204-635-6
MDL Number: MFCD00005495
Beilstein/REAXYS Number: 108440

CAS Number: 123-56-8
3D Model (JSmol): Interactive image
ChEBI: CHEBI:9307
ChEMBL: ChEMBL275661
ChemSpider: 10955
ECHA InfoCard: 100.004.215
PubChem CID: 11439
RTECS Number: WN2200000
UNII: 10X90O3503
CompTox Dashboard (EPA): DTXSID8051629
InChI: InChI=1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)
Key: KZNICNPSHKQLFF-UHFFFAOYSA-N
InChI: InChI=1/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)
Key: KZNICNPSHKQLFF-UHFFFAOYAV
SMILES: O=C1NC(=O)CC1

CAS No.: 123-56-8
Chemical Name: Succinimide
CBNumber: CB4852973
Molecular Formula: C4H5NO2
Molecular Weight: 99.09
MDL Number: MFCD00005495
MOL File: 123-56-8.mol

Product Number: S0108
Purity / Analysis Method: >98.0%(T)
Molecular Formula / Molecular Weight: C4H5NO2 = 99.09
Physical State (20 deg.C): Solid
Storage Temperature: Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 123-56-8
Reaxys Registry Number: 108440
PubChem Substance ID: 87575721
SDBS (AIST Spectral DB): 1410
Merck Index (14): 8871
MDL Number: MFCD00005495

Article No.: 06150
Grade: For Synthesis
Purity: 99%
CAS No.: 123-56-8
Molecular Formula: C4H5NO2
Molecular Weight: 99.09
H.S. Code: 2925.1900

CAS: 123-56-8
IUPAC Name: pyrrolidine-2,5-dione
Molecular Formula: C4H5NO2
InChI Key: KZNICNPSHKQLFF-UHFFFAOYSA-N
SMILES: O=C1CCC(=O)N1
Molecular Weight (g/mol): 99.09

Properties of Succinimide:
Physical State at 20 °C: Solid
Colour: White crystalline
Odour: Odorless
pH Value: 4.5 at 50 g/l at 20 °C
Melting Point / Freezing Point [°C]: 123 - 125 °C
Flash Point [°C]: 201°C
Boiling Point [°C]: 285 - 290 °C
Initial Boiling Point [°C]: 285°C
Final Boiling Point [°C]: 290 °C
Solubility in Water [% weight]: 240 g/L (20°C)

Melting Point: 123-125 °C (lit.)
Boiling Point: 285-290 °C (lit.)
Density: 1.41
Vapor Pressure: <1 hPa (50 °C)
Refractive Index: 1.4166 (estimate)
Flash Point: 201 °C
Storage Temperature: Store below +30°C.
Solubility: 330g/l
pKa: 9.6 (at 25℃)
Form: Powder or Flakes
Color: Off-white to beige to light brown
PH: 4-6 (200g/l, H2O)
Odor: nearly odorless
Water Solubility: Soluble in water and ethanol. Insoluble in ether and chloroform.
Merck: 14,8871
BRN: 108440
InChI: 1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)
InChIKey: KZNICNPSHKQLFF-UHFFFAOYSA-N
SMILES: O=C1CCC(=O)N1
LogP: -0.85 at 20℃
CAS DataBase Reference: 123-56-8 (CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: 10X90O3503
ATC Code: G04BX10
NIST Chemistry Reference: 2,5-Pyrrolidinedione (123-56-8)
EPA Substance Registry System: Succinimide (123-56-8)
UNSPSC Code: 12352209
NACRES: NA.26

Molecular Weight: 99.09 g/mol
XLogP3-AA: -1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 99.032028402 Da
Monoisotopic Mass: 99.032028402 Da
Topological Polar Surface Area: 46.2 Å²
Heavy Atom Count: 7
Complexity: 105
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Chemical Formula: C4H5NO2
Molar Mass: 99.089 g·mol−1
Appearance: White crystalline powder
Density: 1.41 g/cm3
Melting Point: 125 to 127 °C (257 to 261 °F; 398 to 400 K)
Boiling Point: 287 to 289 °C (549 to 552 °F; 560 to 562 K)
Solubility in Water: 0.33 g/mL
Acidity (pKa): 9.5
Magnetic Susceptibility (χ): −47.3·10−6 cm3/mol
Pharmacology:
ATC Code: G04BX10 (WHO)

Product Name: Succinimide
Assay: 99.1%
Quality Segment: 200
Form: powder or crystals
Color: white to off-white
Boiling Point: 285-290 °C (lit.)
Melting Point: 123-125 °C (lit.)
SMILES String: O=C1CCC(=O)N1
InChI: 1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)
InChI Key: KZNICNPSHKQLFF-UHFFFAOYSA-N

Specifications of Succinimide:
Appearance: White to Almost white powder to crystal
Purity (Neutralization titration): min. 98.0 %
Melting Point: 124.0 to 127.0 °C
NMR: confirm to structure

Appearance (Color): White to cream to pale brown
Form: Powder or crystalline powder or flakes
Assay (GC): ≥98.0%
Identification (FTIR): Conforms
Melting Point (clear melt): 119-127°C

Related compounds of Succinimide:

Related Imides:
Maleimide
N-Chlorosuccinimide,
N-Bromosuccinimide

Names of Succinimide:

Preferred IUPAC name:
Pyrrolidine-2,5-dione

Other names:
Succinimide
Succinic acid imide