Phthalimide
| Phthalimide | |
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Isoindole-1,3-dione |
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Other names
Phthalimide |
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| Identifiers | |
| CAS number | 85-41-6  |
| PubChem | 6809 |
| ChemSpider | 6550 |
| ChEBI | CHEBI:38817 |
| ChEMBL | CHEMBL277294 |
| Jmol-3D images | Image 1 |
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| Properties[1] | |
| Molecular formula | C8H5NO2 |
| Molar mass | 147.13 g mol−1 |
| Appearance | White solid |
| Melting point |
238 °C, 511 K, 460 °F |
| Boiling point |
336 °C, 609 K, 637 °F (sublimes) |
| Solubility in water | <0.1 g/100 ml (19.5 °C) |
| Acidity (pKa) | 8.3 |
| Basicity (pKb) | 5.7 |
| Related compounds | |
| Related Amides | Maleimide |
| Related compounds | Phthalic anhydride |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Phthalimide is an imide, which is a chemical compound with two carbonyl groups bound to a secondary amine or ammonia. It is a white solid at room temperature.
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[edit] Preparation
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.
[edit] Uses
Phthalimide is used in plastics, in chemical synthesis, and in research.
[edit] 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, 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[2], is used in the Gabriel synthesis of primary amines, and the Gabriel synthesis of glycine has yields as high as 85%.
[edit] Natural occurrence
Kladnoite is a natural mineral analog of phthalimide.[3] It is very rarely found among few burning coal fire sites.
[edit] References
- ^ "Phthalimide". Chemicalland21. http://www.chemicalland21.com/specialtychem/finechem/PHTHALIMIDE.htm. Retrieved 15 November 2011.
- ^ "β-BROMOETHYLPHTHALIMIDE". Organic Syntheses. http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0119. Retrieved 15 November 2011.
- ^ "Kladnoite". mindat.org. http://www.mindat.org/min-2222.html. Retrieved 15 November 2011.
- Vollhardt, K. Peter C.; Schore, Neil Eric (2002). Organic Chemistry: Structure and Function (4th ed.). New York: W.H. Freeman. ISBN 978-0716743743.
- Finar, Ivor Lionel (1973). Organic Chemistry. 1 (6th ed.). London: Longman. ISBN 0582442214.
