Phthalimide

Base Information

• Chemical Name: Phthalimide
• CAS No.: 85-41-6
• Molecular Formula: C₈H₅NO₂
• Molecular Weight: 147.133
• Hs Code.: 2925.19
• European Community (EC) Number: 201-603-3
• NSC Number: 3108
• UNII: 1J6PQ7YI80
• DSSTox Substance ID: DTXSID3026514
• Nikkaji Number: J4.918B
• Wikipedia: Phthalimide
• Wikidata: Q412784
• Metabolomics Workbench ID: 56017
• ChEMBL ID: CHEMBL277294
• Mol file: 85-41-6.mol

Synonyms:phthalimide;phthalimide calcium (2:1) salt;phthalimide potassium salt;potassium phthalimide

Chemical Property of Phthalimide

Chemical Property:

• Appearance/Colour: white to slightly yellowish crystalline flakes
• Vapor Pressure: 0.001Pa at 25℃
• Melting Point: 232-235 °C(lit.)
• Refractive Index: 1.4700 (estimate)
• Boiling Point: 359 °C at 760 mmHg
• PKA: 8.3(at 25℃)
• Flash Point: 170.9 °C
• PSA: 46.17000
• Density: 1.367 g/cm³
• LogP: 0.89900
• Storage Temp.: Store below +30°C.
• Solubility.: water: slightly soluble(lit.)
• Water Solubility.: <0.1 g/100 mL at 19.5℃
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 147.032028402
• Heavy Atom Count: 11
• Complexity: 190

Purity/Quality:

99% ^*data from raw suppliers

Phthalimide 99+% ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22-36/37/38-40
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Rings
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)NC2=O
• Uses: Phthalimide is a reagent used to transform allyl- and alkyl halides into protected primary amines. Phthalimide analogues have been extensively used in medicinal chemistry owing to their wide spectrum of applications as anti-convulsant, anti-inflammatory, analgesic, hypolipidimic and immunomodulatory activities. Phthalimide, C6H4(CO)2NH, is an imide of commercial and industrial importance, forming a number of interesting derivatives. With alcoholic potash, phthalimide forms a potassium derivative, C6H4 (CO)2 NK, which, when reacted with ethyl iodide (or other alkyl halides), yields ethylphthalimide, C6H4(CO)2 N C2H5. The latter product, when hydrolyzed with an acid or alkali, further yields ethylamine [CAS: 75-04-7] C2H7N. Such reaction chains are useful in the preparation of certain primary amines and their derivatives. Phthalimide is a reagent used to transform allyl- and alkyl halides into protected primary amines. Phthalimide analogues have been extensively used in medicinal chemistry owing to their wide spectrum of applications as anti-convulsant, anti-inflammatory, analgesic, hypolipidimic and immunomodulatory activities. Dyes and metabolites, Environmental Testing.

Technology Process of Phthalimide

There total 155 articles about Phthalimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 21.0%

3-phthalimidopropanoic acid (3339-73-9) → phthalimide (136918-14-4,85-41-6) + N-ethylphthalimide (5022-29-7) + 3,4-dihydro-1H-2-benzazepine-1,5(2H)-dione (41764-17-4)

Guidance literature:

In acetonitrile; for 20h; Irradiation;

DOI:10.1016/S0040-4020(99)00702-4

Reference yield: 16.0%

methanol (67-56-1) + 2,2'-(phenyl-λ3-iodanediyl)bis(isoindoline-1,3-dione) (86451-26-5) → phthalimide (136918-14-4,85-41-6) + methyl 2-((methoxycarbonyl)amino)benzoate (7143-42-2) + 2-carbomethoxyaniline (134-20-3)

Guidance literature:

With [hydroxy(tosyloxy)iodo]benzene; potassium carbonate; sodium sulfate; In acetonitrile; at 20 ℃; for 6h; regioselective reaction;

DOI:10.1021/ol300028j

Reference yield:

N-hydroxyphthalimide (524-38-9) + nitrobenzene (98-95-3,26969-40-4) → phthalimide (136918-14-4,85-41-6) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + 2-hydroxynitrobenzene (88-75-5,78813-12-4)

Guidance literature:

at 270 ℃; for 30h; Mechanism; also with naphthalene;

upstream raw materials:

N-methylaniline

(+/-)-phthaloylaspartic acid

N-bromophthalimide

diethyl ether

Downstream raw materials:

2-(oxan-2-ylmethyl)-2,3-dihydro-1H-isoindole-1,3-dione

2-benzoylisoindoline-1,3-dione

3-quinolin-2-ylmethylene-2,3-dihydro-isoindol-1-one

2-(2-hydroxy-2-(4-nitro-phenyl)-ethyl)-isoindole-1,3-dione

Refernces

• 1、 Chandrachud, Preeti P.,Wojtas, Lukasz,Lopchuk, Justin M.. "Decarboxylative Amination: Diazirines as Single and Double Electrophilic Nitrogen Transfer Reagents". supporting information. p. 21743 - 21750. Retrieved 2021/01/11.
• 2、 Tkachuk, Volodymyr A.,Hordiyenko, Olga V.,Omelchenko, Irina V.,Medviediev, Volodomir V.,Arrault, Axelle. "Methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted α-amino acids as promising building blocks in peptidomimetic synthesis: a comparative study". . p. 2293 - 2309. Retrieved 2018/11/02.