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160385

Sigma-Aldrich

Phthalimide potassium salt

98%

Synonym(s):

1,3-Dihydro-1,3-dioxoisoindole potassium salt, Potassium phthalimide

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About This Item

Empirical Formula (Hill Notation):
C8H4KNO2
CAS Number:
Molecular Weight:
185.22
Beilstein/REAXYS Number:
3598719
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

powder

mp

>300 °C (lit.)

solubility

water: soluble 50 mg/mL, clear to slightly hazy, colorless to yellow

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

Condensation of phthalimide potassium with organic halide in dimethylformamide has been reported. Reaction of potassium phthalimide and sulfur monochloride in petroleum ether has been studied.
Phthalimide potassium salt was employed as organocatalyst for the cyanosilylation of various carbonyl compounds under extremely mild conditions. It was also employed as reagent for the transformation of allyl- and alkyl halides into protected primary amines.

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Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

346.3 °F - closed cup

flash_point_c

174.6 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves


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An improved procedure for the condensation of potassium phthalimide with organic halides.
Sheehan JC and Bolhofer WA.
Journal of the American Chemical Society, 72(6), 2786-2788 (1950)
Tetrahedron Letters, 48, 3043-3043 (2007)
Reactions of Phthalimide and Potassium Phthalimide with Sulfur Monochloride.
Kalnins MV.
Canadian Journal of Chemistry, 44(17), 2111-2113 (1966)
Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.
Jianming Lu et al.
Journal of the American Chemical Society, 129(25), 7768-7769 (2007-06-02)
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)

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