Phthalimide
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| Phthalimide | |
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| General | |
| Systematic name | Isoindole-1,3-dione |
| Other names | Phthalimide |
| Molecular formula | C8H5O2N1 |
| SMILES | O=C2NC(C1=CC=CC=C12)=O |
| Molar mass | 147.13 g/mol |
| Appearance | white solid |
| CAS number | [85-41-6] |
| Properties | |
| Density and phase | ? g/cm3, ? |
| Solubility in water | <0.1 g/100 ml (19.5 °C) |
| Melting point | 238ºC |
| Boiling point | 336ºC (sublimes) |
| Acidity (pKa) | ? |
| Basicity (pKb) | ? |
| Viscosity | ? cP at ?°C |
| Structure | |
| Molecular shape | ? |
| Coordination geometry |
? |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | ?°C |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related Amides | Maleimide |
| Related compounds | Phthalic anhydride |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references |
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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 temperatre.
Contents |
[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, and can be made by reacting phthalimide with metal carbonates. Potassium phthalimide, made by reacting phthalimide with potassium carbonate in water at 100ºC, is used in the Gabriel synthesis of primary amines, and the Gabriel synthesis of glycine has yields as high as 85%.
[edit] References
- Information sheet
- Organic Chemistry: Structure and Function, Fourth Edition, Copyright 2003
[edit] External links
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