ChemicalBook > CAS DataBase List > Succinimide

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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Succinimide Suppliers

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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
Min. Order
1kg
Purity
99.9%
Supply Ability
10000
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
  • SI
  • 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
  • Cyclic Imides
  • Carbonyl Compounds
  • Organic Building Blocks
  • Peptide Synthesis
  • Building Blocks
  • Biochemicals and Reagents
  • Amino Acids and Peptides
  • BioChemical
  • Miscellaneous
  • 123-56-8