Phthalimide is a reagent used to transform allyl- and alkyl halides into protected primary amines. . It is used as a precursor to other organic compounds as a masked source of ammonia.
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Applications
Phthalimide is a reagent used to transform allyl- and alkyl halides into protected primary amines. . It is used as a precursor to other organic compounds as a masked source of ammonia.
Solubility
Slightly soluble in water. Soluble in aqueous alkali hydroxides
Notes
Store at room temperature. Ensure good ventilation.
RUO – Research Use Only
General References:
- John C. Sheehan.; William A. Bolhofer. An Improved Procedure for the Condensation of Potassium Phthalimide with Organic Halides. J. Am. Chem. Soc. 1950, 72 (2), 2786-2788.
- Lıdia M Lima.; Paulo Castro.; Alexandre L Machado.; Carlos Alberto M Fraga.; Claire Lugnier.; Vera Lúcia Gonçalves de Moraes.; Eliezer J Barreiro. Synthesis and anti-inflammatory activity of phthalimide derivatives, designed as new thalidomide analogues. Bioorg. Med. Chem.. 2002, 10 (9),3067-3073.
- For use in the Gabriel synthesis of primary amines, see: Potassium phthalimide, A11134. For an example of N-alkylation in the presence of K2CO3, see: Org. Synth. Coll., 2, 83 (1943). The N-alkylation by alkyl halides can be effected using KF, RbF or CsF as base; NaF and LiF are ineffective: J. Am. Chem. Soc., 99, 498 (1977).
- The direct conversion of alcohols to N-alkylphthalimides and hence to amines can be effected in the presence of the Mitsunobu reagent: Org. Synth. Coll., 7, 501 (1990):