|Jmol-3D images||Image 1|
|Molar mass||147.13 g mol−1|
|Melting point||238 °C (460 °F; 511 K)|
|Boiling point||336 °C (637 °F; 609 K) sublimes|
|Solubility in water||<0.1 g/100 ml (19.5 °C)|
|Related compounds||Phthalic anhydride|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Phthalimide can be prepared by heating phthalic anhydride with aqueous ammonia giving 95-97% yield. Alternatively, it may be prepared by fusing the anhydride with ammonium carbonate.
Phthalimide is used in plastics, in chemical synthesis, and in research. They are useful for protecting amines in chemical synthesis, especially in peptide synthesis where they are used " to block both hydrogens and avoid racemization of the substrates". They are commonly removed with hydrazine, but dimethylamine can also be used.
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, which can be made by reacting phthalimide with metal carbonates. Potassium phthalimide, made by reacting phthalimide with potassium carbonate in water at 100 °C or with potassium hydroxide in absolute ethanol, is used in the Gabriel synthesis of primary amines, and the Gabriel synthesis of glycine has yields as high as 85%.
Kladnoite is a natural mineral analog of phthalimide. It is very rarely found among a few burning coal fire sites.
- "Phthalimide". Chemicalland21. Retrieved 15 November 2011.
- "Phthalimides". Retrieved 2013-02-07.
- "DEPROTECTION – REMOVAL OF AMINE PROTECTING GROUPS (PHTHALIMIDE AND DIMETHYLAMINOSULPHONYL)". Retrieved 2013-02-07.
- "β-BROMOETHYLPHTHALIMIDE". Organic Syntheses. Retrieved 15 November 2011.
- "Kladnoite". mindat.org. Retrieved 15 November 2011.