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Potassium phthalimide

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CAS:1074-82-4
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  • CAS:1074-82-4
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  • Purity: 99%
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  • CAS:1074-82-4
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  • CAS:1074-82-4
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Potassium phthalimide Basic information
Product Name:Potassium phthalimide
Synonyms:1,3-Dihydroisoindole-1,3-dione potassium salt;1H-Isoindole-1,3(2H)-dione,potassiumsalt;n-potassiophthalimide;potassiumphthalimidate;Nsc167070;PotassiumIsoindole-1,3-dione;PotassiuM 1,3-dioxoisoindolin-2-ide;PHTHALIMIDE POTASSIUM SALT FOR SYNTHESIS
CAS:1074-82-4
MF:C8H5NO2.K
MW:186.23
EINECS:214-046-6
Product Categories:Amination;Classes of Metal Compounds;K (Potassium) Compounds (excluding simple potassium salts);N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Synthetic Organic Chemistry;Typical Metal Compounds;pharmaceutical;Dye;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Cyclic Imides;Organic Building Blocks;1074-82-4
Mol File:1074-82-4.mol
Potassium phthalimide Structure
Potassium phthalimide Chemical Properties
Melting point >300°C
Boiling point 366C
density 1.63
storage temp. Inert atmosphere,Room Temperature
solubility water: soluble50mg/mL, clear to slightly hazy, colorless to yellow
pka8.3 (basic)(Solvent: Water)
form Crystalline Powder
color White to yellow or greenish
PHpH (50g/l, 25℃) : 10.5~12.5
Water Solubility Soluble in water.
Sensitive Moisture Sensitive
BRN 3598719
InChIInChI=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
InChIKeyFYRHIOVKTDQVFC-UHFFFAOYSA-M
SMILESC12C=CC=CC=1C(N([K])C2=O)=O
LogP-1.859
CAS DataBase Reference1074-82-4(CAS DataBase Reference)
EPA Substance Registry SystemPotassium phthalimide (1074-82-4)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-24/25-26-60-37
WGK Germany 3
TSCA TSCA listed
HS Code 29251995
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
Hazardous Substances Data1074-82-4(Hazardous Substances Data)
MSDS Information
ProviderLanguage
N-Potassium phthalimide English
ACROS English
SigmaAldrich English
ALFA English
Potassium phthalimide Usage And Synthesis
Chemical Propertiesslight yellow-green to white powder
UsesPotassium phthalimide is usually 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.
UsesPotassium Phthalimide is a green, solid-base organocatalys.
UsesCondensation of phthalimide potassium with organic halide in dimethylformamide has been reported. Reaction of potassium phthalimide and sulfur monochloride in petroleum ether has been studied.
Synthesis
1H-Isoindol-1-one, 3-hydroxy-

136918-14-4

Potassium phthalimide

1074-82-4

General procedure for the synthesis of phthalimide potassium salt from 3-hydroxy-1H-isoindol-1-one: Add phthalimide to the reactor with 3 times the mass of anhydrous ethanol, and heat it up to 60℃. A pre-prepared anhydrous ethanol solution of 30% potassium methanolate (molar ratio of potassium methanolate to phthalimide 1.2:1) was slowly added by dropping through a burette with a controlled dropping time of 3 hours, during which the temperature was slightly elevated (up to a maximum of 65 °C). After the reaction lasted for 10 hours, the reaction mixture was filtered, washed once with anhydrous ethanol, and dried to give a high-purity potassium salt of phthalimide with a purity of 99.3% and a molar yield of 98%.

Purification MethodsThe solid may contain phthalimide and K2CO3 from hydrolysis. If too much hydrolysis has occurred (this can be checked by extraction with cold Me2CO in which the salt is insoluble, evaporate the Me2CO and weigh the residue), it would be better to prepare it afresh. If little hydrolysis has occurred, then recrystallise it from a large volume of EtOH, and wash the solid with a little Me2CO and dry it in a continuous vacuum to constant weight. [Salzerg & Supriawski Org Synth Coll Vol I 119 1941, Raman & IR: Hase J Mol Struct 48 33 1978, Dykman Chem Ind (London) 40 1972, IR, NMR: Assef et al. Bull Soc Chim Fr II 167 1979, Beilstein 21/10 V 270.]
References[1] Patent: CN104447497, 2017, B. Location in patent: Paragraph 0018-0019; 0021; 0023
[2] Patent: CN106699682, 2017, A. Location in patent: Paragraph 0051; 0052
[3] Patent: CN107382980, 2017, A. Location in patent: Paragraph 0027; 0028; 0029; 0030
[4] Patent: CN107540647, 2018, A. Location in patent: Paragraph 0020-0024
[5] Journal of the American Chemical Society, 2011, vol. 133, # 41, p. 16410 - 16413
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