Phthalimide

Chembox new
Name = Phthalimide
ImageFileL1 = Phthalimide.png ImageSizeL1 = 130
ImageNameL1 = skeletal formula of the phthalimide molecule
ImageFileR1 = Phthalimide-3D-balls.png ImageSizeR1 = 150
ImageNameR1 = ball-and-stick model of the phthalimide molecule
IUPACName = Isoindole-1,3-dione
OtherNames = PhthalimidePhthalimidoyl (deprotonated)
Section1 = Chembox Identifiers
SMILES = O=C2NC(C1=CC=CC=C12)=O
CASNo = 85-41-6
RTECS =
Section2 = Chembox Properties
Formula = carbon|8hydrogen|5oxygen|2nitrogen|1
MolarMass = 147.13 g/mol
Appearance = white solid
Density = ? g/cm³, ?
Solubility =<0.1 g/100 ml (19.5 °C)
MeltingPt = 238°C
BoilingPt = 336°C (sublimes)
pKa = 8.3
pKb = 5.7
Viscosity = ? cP at ?°C
Section3 = Chembox Structure
MolShape =
Coordination =
CrystalStruct =
Dipole =
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards =
FlashPt = ?°C
RPhrases =
SPhrases =
Section8 = Chembox Related
Function = Amides
OtherFunctn = Maleimide
OtherCpds = Phthalic anhydride

Phthalimide is an imide, which is a chemical compound with two carbonyl groups bound to a primary amine or ammonia. It is a white solid at room temperature.

Uses

Phthalimide is used in plastics in chemical synthesis, and in research.

Reactivity

It forms salts with various metals such as potassium and sodium due to its high acidity caused by the electrophilic carbonyl groups attached to the nitrogen atom, and can be made by reacting phthalimide with metal carbonates. Potassium phthalimide, made by reacting phthalimide with potassium carbonate in water at 100°C, is used in the Gabriel synthesis of primary amines, and the Gabriel synthesis of glycine has yields as high as 85%.

Natural occurrence

Kladnoite is a natural (mineral) analogue of phthalimide. It is very rarely found among few burning coal fire sites.

References

* [http://www.chemicalland21.com/specialtychem/finechem/PHTHALIMIDE.htm Information sheet]
* Organic Chemistry: Structure and Function, Fourth Edition, Copyright 2003

External links