All Photos(1)
Synonym(s):
PPI, 1,3-Dihydro-1,3-dioxoisoindole potassium salt, Potassium phthalimide
Empirical Formula (Hill Notation):
C8H4KNO2
CAS Number:
Molecular Weight:
185.22
Beilstein:
3598719
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
grade
purum
Quality Level
Assay
≥99.0% (NT)
form
powder
impurities
≤0.5% water
mp
>300 °C (lit.)
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
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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One-pot synthesis of core-expanded naphthalene diimides: enabling N-substituent modulation for diverse n-type organic materials.
Hu Y, et al.
Organic Letters, 14(1), 292-295 (2011)
A facile one-pot synthesis of N-substituted phthalimides using a catalytic amount of crown ether.
Soai K, et al.
Bulletin of the Chemical Society of Japan, 55(5), 1671-1672 (1982)
γ?Aminobutyric Acid
DeWitt C C
Organic Syntheses, 4-4 (1943)
Activation of trimethylsilyl cyanide by potassium phthalimide for facile synthesis of TMS-protected cyanohydrins.
Dekamin MG and Karimi Z.
Journal of Organometallic Chemistry, 694(12), 1789-1794 (2009)
Stanton Hon Lung Kok et al.
Bioorganic & medicinal chemistry, 16(7), 3626-3631 (2008-02-26)
Phthalic anhydride is a highly toxic substance, facing, however, the problem of hydrolysis. In fact, it is rapidly hydrolyzed in aqueous medium, generating phthalic acid as the final product, which is almost harmless to viable cells. Here we describe the
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