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| | Phthalimide Basic information |
| | Phthalimide Chemical Properties |
| Melting point | 232-235 °C(lit.) | | Boiling point | 366 °C | | density | 1.21 | | vapor pressure | 0.001Pa at 25℃ | | refractive index | 1.4700 (estimate) | | Fp | 165 °C | | storage temp. | Store below +30°C. | | solubility | water: slightly soluble(lit.) | | pka | 8.3(at 25℃) | | form | Crystalline Flakes | | color | White to slightly yellow | | PH | 3.8 (0.6g/l, H2O) | | Water Solubility | <0.1 g/100 mL at 19.5 ºC | | Sublimation | 366 ºC | | Merck | 14,7373 | | BRN | 118522 | | InChIKey | XKJCHHZQLQNZHY-UHFFFAOYSA-N | | LogP | 1.15 | | CAS DataBase Reference | 85-41-6(CAS DataBase Reference) | | NIST Chemistry Reference | Phthalimide(85-41-6) | | EPA Substance Registry System | Phthalimide (85-41-6) |
| | Phthalimide Usage And Synthesis |
| Chemical Properties | white to slightly yellowish crystalline flakes | | Uses | Phthalimide is a reagent used to transform allyl- and alkyl halides into protected primary amines. Phthalimide analogues have been extensively used in medicinal chemistry owing to their wide spectrum of applications as anti-convulsant, anti-inflammatory, analgesic, hypolipidimic and immunomodulatory activities. Dyes and metabolites, Environmental Testing. | | Uses | Phthalimide, C6H4(CO)2NH, is an imide of commercial and industrial importance, forming a number of interesting derivatives. With alcoholic potash, phthalimide forms a potassium derivative, C6H4 (CO)2 NK, which, when reacted with ethyl iodide (or other alkyl halides), yields ethylphthalimide, C6H4(CO)2 N C2H5. The latter product, when hydrolyzed with an acid or alkali, further yields ethylamine [CAS: 75-04-7] C2H7N. Such reaction chains are useful in the preparation of certain primary amines and their derivatives. | | Uses | Phthalimide is a reagent used to transform allyl- and alkyl halides into protected primary amines. Phthalimide analogues have been extensively used in medicinal chemistry owing to their wide spectrum
of applications as anti-convulsant, anti-inflammatory, analgesic, hypolipidimic and immunomodulatory activities. | | Definition | ChEBI: A dicarboximide that is 2,3-dihydro-1H-isoindole substituted by oxo groups at positions 1 and 3. | | Synthesis Reference(s) | Journal of the American Chemical Society, 111, p. 3725, 1989 DOI: 10.1021/ja00192a034
The Journal of Organic Chemistry, 45, p. 363, 1980 DOI: 10.1021/jo01290a038
Tetrahedron Letters, 34, p. 6907, 1993 DOI: 10.1016/S0040-4039(00)91827-6 | | General Description | White to light tan powder. Slightly acidic. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | O-Phthalimide is an imide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). O-Phthalimide forms salts with bases. | | Health Hazard | ACUTE/CHRONIC HAZARDS: When heated to decomposition O-Phthalimide emits toxic fumes of nitrogen oxides. | | Fire Hazard | Literature sources indicate that O-Phthalimide is combustible. | | Safety Profile | Moderately toxic by
intraperitoneal route. Mildly toxic by
ingestion. An experimental teratogen. Other
experimental reproductive effects. When
heated to decomposition it emits toxic
fumes of NOx. | | Purification Methods | Crystallise the imide from EtOH (20mL/g) (charcoal), or sublime it. For potassium phthalimide see entry in “Metal-organic Compounds”, Chapter 5. [Beilstein 21/10 V 270.] |
| | Phthalimide Preparation Products And Raw materials |
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