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About This Item
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
Quality Level
Assay
98%
form
powder
mp
>300 °C (lit.)
solubility
water: soluble 50 mg/mL, clear to slightly hazy, colorless to yellow
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
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.
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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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)
Reactions of Phthalimide and Potassium Phthalimide with Sulfur Monochloride.
Kalnins MV.
Canadian Journal of Chemistry, 44(17), 2111-2113 (1966)
Tetrahedron Letters, 48, 3043-3043 (2007)
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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