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1074-82-4 - Potassium phthalimide, 98+% - Phthalimide potassium salt - A11134 - Alfa Aesar

A11134 Potassium phthalimide, 98+%

Numéro CAS
1074-82-4
Synonymes
Phthalimide potassium salt

Dimensions Prix ($) Quantité Disponibilité
100g 26,50
500g 78,50
2500g 311,00
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Potassium phthalimide, 98+%

MDL
MFCD00005887
EINECS
214-046-6

Propriétés chimiques

Formule
C8H4KNO2
Poids formulaire
185.23
Point de fusion
>300°
Densité
1.63
Sensibilité
Moisture Sensitive
Solubilité
Soluble in water.

Applications

Potassium phthalimide is used as an intermediate in the synthesis of N-alkylated phthalimides, which is involved in the preparation of primary amines (Gabriel synthesis) by the hydrolysis reaction. It is also used as an intermediate for synthetic indigo, pigments, dyes and pharmaceuticals. Further, it is employed as an organocatalyst for the cyanosilylation of various carbonyl compounds under extremely mild conditions. In addition to this, it serves as a reagent for the transformation of allyl- and alkyl halides into protected primary amines.

Notes

Moisture sensitive. Incompatible with strong oxidizing agents and strong acids.

Références bibliographiques

For an example of the classical Gabriel synthesis of primary amines from an alkyl halide by alkylation of potassium phthalimide followed by hydrolysis, see: Org. Synth. Coll., 2, 25 (1943). For use of the Gabriel reaction on Merrifield resin as the first step of a synthesis of a polymer-supported carbodiimide, see: Org. Synth. Coll., 6, 951 (1988). The phthalimide alkylation is often carried out in DMF. A liquid-liquid phase-transfer method using (n-Hexadecyl)­tri-n-butyl­phosphonium bromide, L01335, as catalyst also gives excellent results: Synthesis, 389 (1976).

The standard method for cleavage of the N-substituted phthalimide is with hydrazine hydrate, effective under milder conditions than acid or base hydrolysis. Other hydrazines and primary amines have also been successful, e.g. methylhydrazine or N,N-dimethylpropanediamine: Org. Synth. Coll., 9, 13, 16 (1998). Another technique involves borohydride reduction to the hydroxy amide, and liberation of the amine with acetic acid, with cyclization to phthalide: Tetrahedron Lett., 25, 2093 (1984). For suggested improvements to the cleavage conditions in the Gabriel synthesis, see: J. Org. Chem., 61, 8063 (1996). Review of the Gabriel reaction: Angew. Chem. Int. Ed., 7, 919 (1968).

For an alternative approach to the formation of primary amines, see Dibenzyl­amine, A11554.

Kiyokawa, K.; Kosaka, T.; Kojima, T.; Minakata, S. Synthesis and Structure of Hypervalent Iodine(III) Reagents Containing Phthalimidate and Application to Oxidative Amination Reactions. Angew. Chem. Int. Ed. 2015, 127 (46), 13923-13927.

Fesenko, A. A.; Trafimova, L. A.; Albov, D. V.; Shutalev, A. D. Nucleophile-dependent diastereoselectivity in the ring expansion of pyrimidines to give 1,3-diazepines. Tetrahedron Lett. 2015, 56 (11), 1317-1321.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Mentions de prudence: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
3598719
Code tarifaire harmonisé
2925.19
TSCA
Yes

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