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Phthalimide

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Phthalimide Basic information
Phthalimide Chemical Properties
  • Melting point:232-235 °C(lit.)
  • Boiling point:366 °C
  • Density 1.21
  • refractive index 1.4700 (estimate)
  • Flash point:165 °C
  • storage temp. Store below +30°C.
  • solubility water: slightly soluble(lit.)
  • pka8.3(at 25℃)
  • form Crystalline Flakes
  • color White to slightly yellow
  • PH3.8 (0.6g/l, H2O)
  • Water Solubility <0.1 g/100 mL at 19.5 ºC
  • Sublimation 366 ºC
  • Merck 14,7373
  • BRN 118522
  • InChIKeyXKJCHHZQLQNZHY-UHFFFAOYSA-N
  • CAS DataBase Reference85-41-6(CAS DataBase Reference)
  • NIST Chemistry ReferencePhthalimide(85-41-6)
  • EPA Substance Registry SystemPhthalimide (85-41-6)
Safety Information
MSDS
Phthalimide Usage And Synthesis
  • Chemical Propertieswhite to slightly yellowish crystalline flakes
  • UsesPhthalimide 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.
  • UsesPhthalimide, 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.
  • UsesPhthalimide 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.
  • DefinitionChEBI: 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 DescriptionWhite to light tan powder. Slightly acidic.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity ProfileO-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 HazardACUTE/CHRONIC HAZARDS: When heated to decomposition O-Phthalimide emits toxic fumes of nitrogen oxides.
  • Fire HazardLiterature sources indicate that O-Phthalimide is combustible.
  • Safety ProfileModerately 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 MethodsCrystallise 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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