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123-56-8

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Identification

Name
Succinimide
CAS
123-56-8
Synonyms
2,5-DIKETOPYRROLIDENE
2,5-DIKETOPYRROLIDINE
2,5-Dioxopyrrolidine
2,5-PYRROLIDINEDIONE
AKOS BBS-00004334
BUTANIMIDE
SI
SUCCINIC ACID IMIDE
Succinic imide
SUCCINIMIDE
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
Succinimide,~99%
Succinimide, 98+%
EINECS(EC#)
204-635-6
Molecular Formula
C4H5NO2
MDL Number
MFCD00005495
Molecular Weight
99.09
MOL File
123-56-8.mol

Chemical Properties

Appearance
white crystalline powder
Melting point 
123-125 °C (lit.)
mp 
123-125 °C(lit.)

Boiling point 
285-290 °C (lit.)
bp 
285-290 °C(lit.)

density 
1.41
vapor pressure 
<1 hPa (50 °C)
refractive index 
1.4166 (estimate)
Fp 
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)
Water Solubility 
Soluble in water and ethanol. Insoluble in ether and chloroform.
Detection Methods
GC
Merck 
14,8871
BRN 
108440
InChIKey
KZNICNPSHKQLFF-UHFFFAOYSA-N
Uses
Growth stimulants for plants, organic synthesis.
CAS DataBase Reference
123-56-8(CAS DataBase Reference)
NIST Chemistry Reference
2,5-Pyrrolidinedione(123-56-8)
EPA Substance Registry System
123-56-8(EPA Substance)

Questions And Answer(Q&A)

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.
Preparation of Succinimide

Safety Data

Hazard Codes 
Xi
Risk Statements 
R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Statements 
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 .
WGK Germany 
2

RTECS 
WN2200000

TSCA 
Yes
HS Code 
29251995
Toxicity
LD50 orally in rats: 14 g/kg (Melon)

Raw materials And Preparation Products

Material Safety Data Sheet(MSDS)

Hazard Information

Chemical Properties
white crystalline powder
Definition
ChEBI: A dicarboximide that is pyrrolidine which is substituted by oxo groups at positions 2 and 5.
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
Purification Methods
Crystallise the imide from EtOH (1mL/g) or water. [Beilstein 21 H 369, 21/9 V 438.]

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