79790
Phthalimide potassium salt
purum, ≥99.0% (NT)
Synonym(s):
PPI, 1,3-Dihydro-1,3-dioxoisoindole potassium salt, Potassium phthalimide
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About This Item
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grade
purum
Quality Level
Assay
≥99.0% (NT)
form
powder
impurities
≤0.5% water
mp
>300 °C (lit.)
functional group
imide
SMILES string
[K]N1C(=O)c2ccccc2C1=O
InChI
1S/C8H5NO2.K/c10-7-5-3-1-2-4-6(5)8(11)9-7;/h1-4H,(H,9,10,11);/q;+1/p-1
InChI key
FYRHIOVKTDQVFC-UHFFFAOYSA-M
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Application
Phthalimide potassium salt (PPI) is widely used for the synthesis of primary amines from corresponding alkyl halides, known as Gabriel synthesis. Some of the other applications are:
- Preparation of phthalimidogold precatalyst for gold catalysis.
- It can be used in the palladium-catalyzed enantioselective synthesis of α- and β-amino acids.
- Potassium phthalimide is as an effective organocatalyst for the cyanosilylation of carbonyl compounds to synthesize cyanohydrin trimethylsilyl ethers.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
346.3 °F - closed cup
Flash Point(C)
174.6 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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A facile one-pot synthesis of N-substituted phthalimides using a catalytic amount of crown ether.
Bulletin of the Chemical Society of Japan, 55(5), 1671-1672 (1982)
One-pot synthesis of core-expanded naphthalene diimides: enabling N-substituent modulation for diverse n-type organic materials.
Organic Letters, 14(1), 292-295 (2011)
γ?Aminobutyric Acid
Organic Syntheses, 4-4 (1943)
Activation of trimethylsilyl cyanide by potassium phthalimide for facile synthesis of TMS-protected cyanohydrins.
Journal of Organometallic Chemistry, 694(12), 1789-1794 (2009)
Palladium-catalysed asymmetric allylic substitution: synthesis of α-and β-amino acids.
Journal of the Chemical Society. Perkin Transactions 1, 9, 1411-1420 (1997)
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