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79790

Sigma-Aldrich

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
Beilstein:
3598719
EC Number:
214-046-6
MDL number:
MFCD00005887
UNSPSC Code:
12352100
PubChem Substance ID:
329768624
NACRES:
NA.22

grade

purum

Quality Level

200

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

79790-500G:
79790-BULK:
79790-100G:
79790-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD1711
BCCC6724
BCCB5113
BCCB1795
BCBZ5643

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γ?Aminobutyric Acid
DeWitt C C
Organic Syntheses, 4-4 (1943)
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)
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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