Succinimide: Difference between revisions

Succinimide
Names
	IUPAC name Pyrrolidine-2,5-dione
	Other names Succinimide; Succinic acid imide
Identifiers
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=1/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7) Key: KZNICNPSHKQLFF-UHFFFAOYAV;
	SMILES O=C1NC(=O)CC1;
Properties
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)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Irritant; Slightly Flammable
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	14 g/kg (rat, oral)
Safety data sheet (SDS)	External MSDS
Related compounds
Related Imides	Maleimide, N-Chlorosuccinimide, N-Bromosuccinimide
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 10:37, 2 November 2018

Succinimide is an organic compound with the formula (CH₂)₂(CO)₂NH. This white solid is used in a variety of organic syntheses, as well as in some industrial silver plating processes. The compound is classified as a cyclic imide. It may be prepared by thermal decomposition of ammonium succinate.^[2]

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.

References

^ ^a ^b Merck Index, 12th Edition, 9040
^ H. T. Clarke and Letha Davies Behr "Succinimide" Organic Syntheses 1936, volume 16, 75. doi:10.15227/orgsyn.016.0075

[Merck-1] Merck Index, 12th Edition, 9040

[2] H. T. Clarke and Letha Davies Behr "Succinimide" Organic Syntheses 1936, volume 16, 75. doi:10.15227/orgsyn.016.0075

[1]

[2]

@@ Line 39: / Line 39: @@
 | Density = 1.41 g/cm<sup>3</sup>
 | Appearance = White crystalline powder
-| Solubility = 1 g/3 mL
+| Solubility = 0.33 g/mL
 | MeltingPtC = 125 to 127
 | BoilingPtC = 287 to 289
@@ Line 63: / Line 63: @@
 }}
-'''Succinimide''' is an [[organic compound]] with the formula (CH<sub>2</sub>)<sub>2</sub>(CO)<sub>2</sub>NH. This white solid is used in a variety of organic syntheses, as well as in some industrial silver plating processes. The compound is classified as a cyclic [[imide]]. It may be prepared by [[thermal decomposition]] of [[ammonium]] [[Succinic acid|succinate]].<ref>H. T. Clarke and Letha Davies Behr "Succinimide" Organic Syntheses 1936, volume 16, 75. {{DOI|10.15227/orgsyn.016.0075}}</ref> Succinimide is soluble in many different liquids including water. However, it would take approximately 4.8 mL of water to dissolve 1g of succinimide.
+'''Succinimide''' is an [[organic compound]] with the formula (CH<sub>2</sub>)<sub>2</sub>(CO)<sub>2</sub>NH. This white solid is used in a variety of organic syntheses, as well as in some industrial silver plating processes. The compound is classified as a cyclic [[imide]]. It may be prepared by [[thermal decomposition]] of [[ammonium]] [[Succinic acid|succinate]].<ref>H. T. Clarke and Letha Davies Behr "Succinimide" Organic Syntheses 1936, volume 16, 75. {{DOI|10.15227/orgsyn.016.0075}}</ref>
 ==Succinimides==
-Succinimides refers to compounds that contain the succinimide group, although they are generally not made from succinimide itself.  These compounds have some notable uses. Several succinimides are used as [[anticonvulsant]] drugs, including [[ethosuximide]], [[phensuximide]], and [[methsuximide]].
+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.<!--referring to maleimide derivatives?-->

Revision as of 10:37, 2 November 2018

Succinimides

See also

References