Phthalimide

Phthalimide is the organic compound with the formula C6H4(CO)2NH. It is the imide derivative of phthalic anhydride. It is a sublimable white solid that is slightly soluble in water but more so upon addition of base. It is used as a precursor to other organic compounds as a masked source of ammonia.

Not to be confused with Thalidomide.
Phthalimide
Names
Preferred IUPAC name
1H-Isoindole-1,3(2H)-dione
Other names
1,3-dioxoisoindoline
Phthalimidoyl (deprotonated)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.458
UNII
  • InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)8(11)9-7/h1-4H,(H,9,10,11) Y
    Key: XKJCHHZQLQNZHY-UHFFFAOYSA-N Y
  • InChI=1/C8H5NO2/c10-7-5-3-1-2-4-6(5)8(11)9-7/h1-4H,(H,9,10,11)
    Key: XKJCHHZQLQNZHY-UHFFFAOYAS
  • O=C2c1ccccc1C(=O)N2
Properties
C8H5NO2
Molar mass 147.133 g·mol−1
Appearance White solid
Melting point 238 °C (460 °F; 511 K)
Boiling point 336 °C (637 °F; 609 K) sublimes
<0.1 g/100 ml (19.5 °C)
Acidity (pKa) 8.3
Basicity (pKb) 5.7
−78.4×10−6 cm3/mol
Related compounds
Related Amides
 Maleimide
Related compounds
 Phthalic anhydride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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