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

A11134 Potassium phthalimide, 98+%

CAS Number
1074-82-4
Synonyms
Phthalimide potassium salt

Size Price ($) Quantity Availability
100g 23.04
500g 71.37
2500g 277.20
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Potassium phthalimide, 98+%

MDL
MFCD00005887
EINECS
214-046-6

Chemical Properties

Formula
C8H4KNO2
Formula Weight
185.23
Melting point
>300°
Density
1.63
Sensitivity
Moisture Sensitive
Solubility
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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

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

Precautionary Statements: 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.

Other References

Beilstein
3598719
Harmonized Tariff Code
2925.19
TSCA
Yes

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