PRODUCTS

POTASSIUM PHTHALIMIDE

Potassium phthalimide is a chemical compound of formula C8H4KNO2.
Potassium phthalimide is the potassium salt of phthalimide, and usually presents as fluffy, very pale yellow crystals.
Potassium phthalimide can be prepared by adding a hot solution of phthalimide in ethanol to a solution of potassium hydroxide in ethanol; the desired product precipitates.

CAS Number: 1074-82-4
Molecular Formula: C8H4KNO2
Molecular Weight (g/mol): 185.22

Potassium phthalimide is a commercially available reagent used in the Gabriel synthesis of amines.

Potassium phthalimide is used as an intermediate in the synthesis of N-alkylated phthalimides, which is involved in the preparation of primary amines (Gabriel synthesis) by the hydrolysis reaction.
Potassium phthalimide is also used as an intermediate for synthetic indigo, pigments, dyes and pharmaceuticals.

Further, Potassium phthalimide is employed as an organocatalyst for the cyanosilylation of various carbonyl compounds under extremely mild conditions.
In addition to this, Potassium phthalimide serves as a reagent for the transformation of allyl- and alkyl halides into protected primary amines.

Potassium phthalimide has also been shown to be active against HIV infection and may be useful for other diseases involving virus infections.
Potassium phthalimide binds covalently with HLA proteins on the surface of infected cells and inhibits viral replication by preventing reverse transcription.

This substance is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.
This substance is used at industrial sites and in manufacturing.

Potassium phthalimide 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.

Potassium phthalimide 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.

Potassium phthalimide is a chemical that reacts with oxygen nucleophiles to form the corresponding N-hydroxyphthalimide.
Potassium phthalimide has been shown as an effective treatment for cancer by targeting tumor cells and inhibiting their growth.

The mechanism of action involves binding to 5-HT2 receptors in the cell membrane, which leads to inhibition of the enzyme adenylate cyclase, leading to decreased levels of cAMP.
This decreases the activity of protein kinase A, which in turn leads to decreased production of proteins such as p21WAF1/CIP1, which are required for cell cycle progression.

Potassium phthalimide (PPI) is employed as an efficient and effective basic organocatalyst for the one-pot three-component reaction of β-oxoesters with hydroxylamine hydrochloride and various aromatic aldehydes.
This cyclocondensation reaction was performed in water as an environmentally benign solvent at room temperature giving 3,4-disubstituted isoxazol-5(4H)-ones in good to excellent yields.

Potassium phthalimide was found to be an effective organocatalyst for the synthesis of isoxazol-5(4H)-one system.
The advantages of this method are efficiency, clean, easy work-up, high yields, shorter reaction times, inexpensive, and readily available catalyst.

Potassium phthalimide, K+.C8H4NO2-, a widely used reagent for the preparation of anthranilic acid via Hofmann degradation or primary alkylamines via the Gabriel synthesis, crystallizes in polar layers of potassium cations coordinated by five O and three N centres alternating with apolar layers of stacked benzene subunits.

Potassium phthalimide is as an excellent absorbent for equimolar CO2 capture with simultaneous activation.
The in situ catalytic conversion of captured CO2 can be successfully converted into value-added chemicals and fuel-related products under mild conditions through a carbon capture and utilization pathway, rather than going through desorption process.

Potassium phthalimide, with weak basicity, is an excellent absorbent for rapid carbon dioxide capture with almost equimolar absorption.
This process is assumed to proceed through the potassium carbamate formation pathway, as supported by NMR spectroscopy, an in situ FTIR study, and computational calculations.

Both the basicity and nucleophilicity of phthalimide salts have a crucial effect on the capture process.
Furthermore, the captured carbon dioxide could more easily be converted in situ into value-added chemicals and fuel-related products through carbon capture and utilization, rather than going through a desorption process.

Applications of Potassium phthalimide:
Potassium phthalimide is used as an intermediate in the synthesis of N-alkylated phthalimides, which is involved in the preparation of primary amines (Gabriel synthesis) by the hydrolysis reaction.
Potassium phthalimide is also used as an intermediate for synthetic indigo, pigments, dyes and pharmaceuticals.

Condensation of Potassium phthalimide with organic halide in dimethylformamide has been reported.
Reaction of potassium phthalimide and sulfur monochloride in petroleum ether has been studied.

Potassium phthalimide salt was employed as organocatalyst for the cyanosilylation of various carbonyl compounds under extremely mild conditions.
Potassium phthalimide was also employed as reagent for the transformation of allyl- and alkyl halides into protected primary amines.

Potassium phthalimide is used as organocatalyst for the cyanosilylation of various carbonyl compounds under extremely mild conditions, and also used as reagent for the transformation of allyl- and alkyl halides into protected primary amines.
Potassium phthalimide is used as an intermediate in the synthesis of N-alkylated phthalimide, which is involved in the preparation of primary amines (Gabriel synthesis) by the hydrolysis reaction.

Potassium phthalimide is also used as an intermediate for synthetic indigo, pigments, dyes and pharmaceuticals.
Potassium phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and saccharin.

Potassium phthalimide is also used for pharma intermediate.

Uses of Potassium phthalimide:

Uses at industrial sites:
This substance is used in the following products: laboratory chemicals.
This substance has an industrial use resulting in manufacture of another substance (use of intermediates).

This substance is used in the following areas: formulation of mixtures and/or re-packaging and scientific research and development.
This substance is used for the manufacture of: chemicals.
Release to the environment of this substance can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.

Handling and Storage of Potassium phthalimide:

Storage conditions:
Tightly closed.
Moisture sensitive.

Storage class:
Storage class (TRGS 510): 11: Combustible Solids

Storage Condition:
Keep container tightly closed in a dry and well-ventilated place.
Protected from moisture.

Stability and Reactivity of Potassium phthalimide:

Reactivity
Forms explosive mixtures with air on intense heating.
A range from approx. 15 Kelvin below the flash point is to be rated as critical.

The following applies in general to flammable organic substances and mixtures:
In correspondingly fine distribution, when whirled up a dust explosion potential may generally be assumed.

Chemical stability:
Potassium phthalimide is chemically stable under standard ambient conditions (room temperature).

Conditions to avoid:
Strong heating.

First Aid Measures of Potassium phthalimide:

General advice:
Show Potassium phthalimide safety data sheet to the doctor in attendance.

After inhalation:
Fresh air.

In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.

After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.

After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.

Firefighting Measures of Potassium phthalimide:

Suitable extinguishing media:
Water Foam Carbon dioxide (CO2) Dry powder

Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.

Special hazards arising from the substance or mixture:
Carbon oxides
Nitrogen oxides (NOx)
Potassium oxides

Combustible.
Vapors are heavier than air and may spread along floors.

Forms explosive mixtures with air on intense heating.
Development of hazardous combustion gases or vapours possible in the event of fire.

Advice for firefighters:
Stay in danger area only with self-contained breathing apparatus.
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.

Further information:
Suppress (knock down) gases/vapors/mists with a water spray jet.
Prevent fire extinguishing water from contaminating surface water or the ground water system.

Accidental release measures of Potassium phthalimide:

Personal precautions, protective equipment and emergency procedures:

Advice for non-emergency personnel:
Avoid inhalation of dusts.
Avoid substance contact.
Ensure adequate ventilation.
Evacuate the danger area, observe emergency procedures, consult an expert.

Environmental precautions:
Do not let product enter drains.

Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.

Observe possible material restrictions.
Take up dry.

Dispose of properly.
Clean up affected area.
Avoid generation of dusts.

Identifiers of Potassium phthalimide:
CAS Number: 1074-82-4
ChemSpider: 10627162
ECHA InfoCard: 100.012.770
PubChem CID: 3356745
UNII: X6KKA27DIL
CompTox Dashboard (EPA): DTXSID5027358
InChI: 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
Key: FYRHIOVKTDQVFC-UHFFFAOYSA-N
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
Key: FYRHIOVKTDQVFC-UHFFFAOYAD
Key: FYRHIOVKTDQVFC-UHFFFAOYSA-N
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: C1=CC=C2C(=C1)C(=O)[N-]C2=O.[K+]

CAS: 1074-82-4
Molecular Formula: C8H4KNO2
Molecular Weight (g/mol): 185.22
MDL Number: MFCD00005887
InChI Key: FYRHIOVKTDQVFC-UHFFFAOYSA-M
PubChem CID: 3356745
IUPAC Name: potassium;isoindol-2-ide-1,3-dione
SMILES: [K+].O=C1[N-]C(=O)C2=CC=CC=C12

Properties of Potassium phthalimide:
Chemical formula: C8H4KNO2
Molar mass: 185.221 g/mol
Appearance: Light yellow solid
Melting point: > 300 °C (572 °F; 573 K)
Solubility in water: Soluble in water

Molecular Weight: 185.22 g/mol
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 0
Exact Mass: 184.98790986 g/mol
Monoisotopic Mass: 184.98790986 g/mol
Topological Polar Surface Area: 35.1Å²
Heavy Atom Count: 12
Complexity: 195
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 2
Compound Is Canonicalized: Yes

Specifications of Potassium phthalimide:
Melting Point: >300°C
Color: Green or White to Yellow
Infrared Spectrum: Authentic
Assay Percent Range: 99%
Packaging: Plastic bottle
Quantity: 100 g
Solubility Information: Solubility in water: soluble in water
Formula Weight: 185.22
Percent Purity: 99%
Physical Form: Crystalline Powder
Chemical Name or Material: Phthalimide, potassium derivative

Melting Point: >300°C
Density: 1.63
Quantity: 500 g
Beilstein: 3598719
Sensitivity: Moisture sensitive
Solubility Information: Soluble in water.
Formula Weight: 185.23
Percent Purity: ≥98%
Chemical Name or Material: Potassium phthalimide

Related compounds of Potassium phthalimide:
Phthalimide

Related Products of Potassium phthalimide:
N,N-Dimethylanilinium Tetrakis(pentafluorophenyl)borate
(R)-(-)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine
Dichlorophenylphosphine
N,N-Dimethyl-1,3-propylenediamine
N,N-Dimethyl-1,3-propylenediamine-d6

Names of Potassium phthalimide:

Regulatory process names:
N-potassium phthalimide

IUPAC names:
1H-ISOINDOLE-1,3(2H)-DIONE POTASSIUM(+1) (1:1)
N-Potassium phthalimide
N-potassium phthalimide
N-potassium phthalimide
Phthalimide Potassium Salt
potassium 1,3-dioxo-1,3-dihydroisoindol-2-ide
Potassium phthalimide
potassium;isoindol-2-ide-1,3-dione

Trade names:
Phthalimide potassium

Other identifiers:
1074-82-4

Synonyms of Potassium phthalimide:
(1,3-dioxoisoindolin-2-yl) potassium
(1,3-dioxoisoindolin-2-yl)potassium
1,3-Dihydro-1,3-dioxoisoindole potassium salt
1,3-Dihydroisoindole-1,3-dione potassium salt
10.14272/FYRHIOVKTDQVFC-UHFFFAOYSA-M.1
1074-82-4
1H-Isoindole-1,3(2H)-dione, potassium salt
1H-Isoindole-1,3(2H)-dione, potassium salt (1:1)
2-potassio-2,3-dihydro-1H-isoindole-1,3-dione
A801706
AC7863
AKOS000121936
AKOS034830283
AM90358
BCP26871
BP-21214
C8-H5-N-O2.K
C8H5NO2.K
CAS-1074-82-4
CHEMBL3183390
CS-0015141
doi:10.14272/FYRHIOVKTDQVFC-UHFFFAOYSA-M.1
DTXCID007358
DTXSID5027358
EINECS 214-046-6
EN300-31459
F1908-0080
FT-0640165
FT-0651552
HSDB 5781
J-001904
J-524025
LS-195293
MFCD00005887
N-Potassiophthalimide
N-Potassium phthalimide
NCGC00258560-01
NSC 167070
NSC-167070
P0403
Phthalimide potassium salt
Phthalimide potassium salt, 98%
Phthalimide potassium salt, purum, >=99.0% (NT)
Phthalimide, potassium salt
potassium 1,3-dioxo-1,3-dihydroisoindol-2-ide
potassium 1,3-dioxo-2,3-dihydro-1H-isoindol-2-ide
Potassium 1,3-dioxoisoindolin-2-ide
Potassium Phtahlimide
Potassium phthalimidate
POTASSIUM PHTHALIMIDE
POTASSIUM PHTHALIMIDE [HSDB]
Potassium phthalylimide
Q413572
SB64015
SCHEMBL9230
SY001384
Tox21_201007
UNII-X6KKA27DIL
X6KKA27DIL
1H-Isoindol-1,3(2H)-dion -kalium (1:1) [German] [ACD/IUPAC Name]
1H-Isoindole-1,3(2H)-dione - potassium (1:1) [ACD/IUPAC Name]
1H-Isoindole-1,3(2H)-dione - potassium (1:1) [French] [ACD/IUPAC Name]
1H-Isoindole-1,3(2H)-dione, potassium salt (1:1) [ACD/Index Name]
potassium phthalimide
1074-82-4 [RN]