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Merck
CN

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

Empirical Formula (Hill Notation):
C8H4KNO2
CAS Number:
1074-82-4
Molecular Weight:
185.22
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
329768624
EC Number:
214-046-6
Beilstein/REAXYS Number:
3598719
MDL number:
MFCD00005887

Key Documents

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Product Name

Phthalimide potassium salt, purum, ≥99.0% (NT)

InChI key

FYRHIOVKTDQVFC-UHFFFAOYSA-M

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

SMILES string

[K]N1C(=O)c2ccccc2C1=O

grade

purum

assay

≥99.0% (NT)

form

powder

impurities

≤0.5% water

mp

>300 °C (lit.)

functional group

imide

Quality Level

200

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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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN8957
BCCM2709
BCCH4018
BCCJ2164
BCCD1711

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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)
Palladium-catalysed asymmetric allylic substitution: synthesis of α-and β-amino acids.
Bower J F, et al.
Journal of the Chemical Society. Perkin Transactions 1, 9, 1411-1420 (1997)
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)
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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