Succinimide

ChemicalBook > CAS DataBase List > Succinimide

Product Name: Succinimide
CAS No.: 123-56-8
Chemical Name: Succinimide
Synonyms: SI;Pyrrolidine-2,5-dione;2,5-PYRROLIDINEDIONE;3,4-Dihydropyrrole-2,5-dione;Lubrizol 2153;succiminide;Succinic imide;Orotric;BUTANIMIDE;SUCCINIMIDE
CBNumber: CB4852973
Molecular Formula: C4H5NO2
Formula Weight: 99.09
MOL File: 123-56-8.mol

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Succinimide Property

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 temp.: 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
InChIKey: KZNICNPSHKQLFF-UHFFFAOYSA-N
LogP: -0.85 at 20℃
CAS DataBase Reference: 123-56-8(CAS DataBase Reference)
NIST Chemistry Reference: 2,5-Pyrrolidinedione(123-56-8)
EPA Substance Registry System: Succinimide (123-56-8)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 22-24/25-36-26-S24/25
WGK Germany: 2
RTECS: WN2200000
TSCA: Yes
HS Code: 29251995
Toxicity: LD50 orally in rats: 14 g/kg (Melon)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 8.07971
Product name: Succinimide
Purity: for synthesis
Packaging: 250g
Price: $65.5
Updated: 2024/03/01

Sigma-Aldrich

Product number: S9381
Product name: Succinimide
Packaging: 500g
Price: $117
Updated: 2024/03/01

Sigma-Aldrich

Product number: 8.07971
Product name: Succinimide
Purity: for synthesis
Packaging: 1kg
Price: $233
Updated: 2024/03/01

TCI Chemical

Product number: S0108
Product name: Succinimide
Purity: >98.0%(T)
Packaging: 25g
Price: $18
Updated: 2024/03/01

TCI Chemical

Product number: S0108
Product name: Succinimide
Purity: >98.0%(T)
Packaging: 500g
Price: $67
Updated: 2024/03/01

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Succinimide Chemical Properties,Usage,Production

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

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.

Uses

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.

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.

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 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 Reference(s)

Journal of the American Chemical Society, 102, p. 7448, 1980 DOI: 10.1021/ja00545a009
Organic Syntheses, Coll. Vol. 2, p. 562, 1943

Flammability and Explosibility

Non flammable

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.]

Succinimide Preparation Products And Raw materials

Raw materials

Succinic acid

Preparation Products

N-Iodosuccinimide β-Alanine N-Bromosuccinimide Cilastatin N-Vinyl-2-pyrrolidone N-Chlorosuccinimide Dichloroacetonitrile 3-AMINO-1-PHENOXY-2-PROPANOL HYDROCHLORIDE

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View Lastest Price from Succinimide manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd

Product: Succinimide 123-56-8
Price: US $10.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20 ton
Release date: 2024-12-13

Hebei Miaoyin Technology Co.,Ltd

Product: Succinimide 123-56-8
Price: US $40.00/kg
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Purity: 99.9%
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Release date: 2023-04-07

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD

Product: Succinimide 123-56-8
Price: US $100.00-75.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 5000
Release date: 2024-08-22

123-56-8, SuccinimideRelated Search:

Bismaleimide O-Phthalimide Succinic acid Succinic anhydride Potassium phthalimide Maleimide Diisopropyl succinate MONO-METHYL SUCCINATE Dimethyl succinate Ascoric Acid DIALIFOS 1-Chloro-pyrrolidine-2,5-dione N-Bromosuccinimide CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE ALPHA-METHYL-ALPHA-PROPYLSUCCINIMIDE N-(2-Chlorobenzyloxycarbonyloxy)succinimide CBZOSU, BENZYLOXYCARBONYL N-SUCCINIMIDE,Z-Osu(N-(Benzyloxycarbonyloxy)Succinimide),Cbz-OSu (Nα-(Benzyloxycarbonyloxy) Succinimide) N-Hydroxysuccinimide

3,4-Dihydropyrrole-2,5-dione

Succinic imide

SUCCINIMIDE

SUCCINIC ACID IMIDE

3,4-Dihydropyrrolidinone

2-Hydroxy-1-pyrroline-5-one

succiminide

Succinimide,2,5-Pyrrolidinedione

SUCCINIMIDE FOR SYNTHESIS 1 KG

SUCCINIMIDE FOR SYNTHESIS 250 G

ALS (SodiuM allyl sulfonate)

Succinimide Vetec(TM) reagent grade, 98%

Succinimide≥ 99% (HPLC)

Ozagrel Impurity 13

Letrozole Impurity 22

3,4-dihydropyrrolidine

Dihydro-3-pyrroline-2,5-dione

Lubrizol 2153

Lubrizol 6406

Orotric

Pyrrolidine-2,5-dione

Succinimide-Sauba

Succinimide,~99%

Succinimide, 98+%

succinimide, butanimide

BUTANIMIDE,SUCCINIMIDE,2.5-PYRROLIDINEDIONE,2.5-DIKETOPYRROLIDINE

2,5-Pyrrolidinone

BUTANIMIDE

AKOS BBS-00004334

2,5-DIKETOPYRROLIDENE

2,5-DIKETOPYRROLIDINE

2,5-PYRROLIDINEDIONE

2,5-Dioxopyrrolidine

Succinimide &gt

Succinimide CAS 123-56-8 with Favorable Price

Succinimide (Butanimide) extrapure AR, 99%

Butadiene imide

Ozagrel Sodium Impurity 13

Succinimide, ≥ 98.0%

123-56-8

123-56-4

CH2CO2NH

KETONE

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Carbonyl Compounds

Organic Building Blocks

Peptide Synthesis

Building Blocks

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Amino Acids and Peptides

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123-56-8