136918-14-4

Basic information

• Product Name: phthalimide
• Synonyms: phthalimide
• CAS NO: 136918-14-4
• Molecular Weight: 147.133
• Mol File: 136918-14-4.mol
• Article Data: 124

Chemical Properties

• CAS DataBase Reference: phthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: phthalimide(136918-14-4)
• EPA Substance Registry System: phthalimide(136918-14-4)

Safety Data

• Hazardous Substances Data: 136918-14-4(Hazardous Substances Data)

Usage

Chemical Description

Different sources of media describe the Chemical Description of 136918-14-4 differently. You can refer to the following data:
1. Phthalimide, diethyl azodicarboxylate, triphenylphosphine, and hydrazine monohydrate are reagents used in the synthesis of the compounds.
2. Phthalimide and methyl toluenesulfonamide are amides that contain a nitrogen atom attached to a carbonyl group.
3. Phthalimide is a cyclic imide compound that can be used as a protecting group for amines.

Upstream product

• 100-61-8 N-methylaniline 
• 4443-39-4 (+/-)-phthaloylaspartic acid 
• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 2142-01-0 N-benzylphthalimide 
• 94-36-0 dibenzoyl peroxide 
• 85-44-9 phthalic anhydride 
• 55-21-0 benzamide 
• 17356-08-0 thiourea 
• 57-13-6 urea 
• 2439-85-2 N-bromophthalimide 
• 60-29-7 diethyl ether 
• 996-82-7 sodium diethylmalonate 
• 71-43-2 benzene 

Downstream Products

• 3891-07-4 N-(2-Hydroxyethyl)phthalimide 
• 550-44-7 N-methylphthalimide 
• 4667-76-9 2-(piperidin-1-ylmethyl)-1,3-dihydroisoindoline-1,3-dione 
• 6857-12-1 N-morpholin-4-ylmethyl-phthalimide 
• 35645-98-8 2-(2-hydroxy-2-phenyl-ethyl)-isoindole-1,3-dione 
• 5394-18-3 2-(4-bromobutyl)isoindoline-1,3-dione 
• 3623-90-3 1,4-bis(phthalimido)butane 
• 1515-72-6 N-butylphthalimide 
• 3197-25-9 2-(4-oxopentyl)isoindole-1,3-dione 
• 5022-29-7 N-ethylphthalimide 
• 74873-98-6 N-(N-benzyl-anilinomethyl)-phthalimide 
• 116595-37-0 N-(2-bromo-4-methyl-anilinomethyl)-phthalimide 
• 6629-44-3 N-(2,5-dimethyl-anilinomethyl)-phthalimide 
• 116594-79-7 N-[2-(2-hydroxy-ethyl)-anilinomethyl]-phthalimide 

Relevant articles and documents

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Exploratory studies probing the intermediacy of azomethine ylides in the photochemistry of N-phthaloyl derivatives of α-amino acids and β-amino alcohols

Exploratory photochemical studies with N-phthaloyl derivatives of glutamic acid, aspartic acid, serine, threonine and analogous carboxylic acids and alcohols have been conducted to determine the generality of azomethine ylide forming decarboxylation and retro-aldol fragmentation reactions. Preferences in the competition between these excited state reaction pathways have been determined by studies with phthalimides which contain both α-amino acid and β-aminoethanol groups.

Spectroscopic and analysis of the hydrolytic process of folpet and its interaction with DNA

Hydrolysis of the pesticide folpet [N-(trichloromethylthio) phthalimide] in aqueous solution in the absence or presence of calf thymus DNA (ctDNA) was investigated using UV-Vis absorption spectroscopy, and the interactions of folpet and its hydrolyzates with ctDNA were determined by fluorescence and circular dichroism spectroscopy, coupled with viscosity and melting temperature measurements. The absorption spectra data was further analyzed by alternate least squares, a chemometrics method, and the concentration profiles of the reacting species (folpet, unstable intermediate, phthalimide and phthalic acid) and their pure component spectra were simultaneously extracted to monitor the hydrolytic process. It was found that the hydrolytic process consists of at least two steps, generation of an unstable intermediate and production of its end hydrolyzates, phthalimide and phthalic acid. Addition of ctDNA significantly affects the hydrolysis of folpet. The results from the competitive binding with intercalator ethidium bromide, ctDNA melting and viscosity measurements, and circular dichroism studies indicate that folpet and the intermediate can intercalate into the double-helix of DNA, phthalic acid is bound to DNA by a partial intercalation, while phthalimide does not show binding to ctDNA. Moreover, the binding of folpet (or the intermediate) and phthalic acid to ctDNA induced structural changes of the DNA.

Photochemical Chlorodecarboxylation via an Electron Transfer Mechanism

A new method of chlorodecarboxylation of carboxylic acids via N-acyloxyphthalimides is developed; the reaction proceeds upon irradiation of N-acyloxyphthalimides in the presence of 1,4-diazabicyclooctane in ButOH-CCl4-H2O (53:42:5 v/v) in moderate to high yields.

Use of Standard Addition to Quantify in Situ FTIR Reaction Data

FTIR spectroscopy is a common in situ reaction monitoring technique used in modern academic and industrial environments. The FTIR signals collected during the course of a reaction are proportional to the concentration of the reaction components but not intrinsically quantitative. To make FTIR data quantitative, precalibration or offline analyses of reaction samples are required, which diminishes the unique benefits of in situ reaction monitoring techniques. Herein, we report the use of standard addition as a convenient method to obtain quantitative FTIR data.

Oxidative C-O cross-coupling of 1,3-dicarbonyl compounds and their heteroanalogues with N-substituted hydroxamic acids and N-hydroxyimides

The oxidative C-O cross-coupling of 1,3-dicarbonyl compounds and their heteroanalogues, 2-substituted malononitriles and cyanoacetic esters, with N-substituted hydroxamic acids and N-hydroxy- imides was realized. The best results were obtained with the use of manganese (III) acetate [Mn (OAc) 3] or the cobalt(II) acetate catalyst [Co (OAc)2cat.]/ potassium permanganate [KMnO4] system as the oxidant. The synthesis can be scaled up to gram quantities of coupling products; yields are 30-94%. The reaction proceeds via a radical mechanism through the formation of nitroxyl radicals from N-substituted hydroxamic acids and N-hydroxyimides.

Incorporation of molecular nitrogen into organic compounds. Titanium catalyzed nitrogenation

Incorporation of molecular nitrogen into organic compounds was realized using a catalytic amount of TiCl4 in the presence of excess TMSCl and Li under nitrogen.

Dual linker with a reference cleavage site for information rich analysis of polymer-supported transformations

Two dual linker systems with specific reference cleavage sites were designed and synthesized to accelerate and simplify development and optimization of reaction conditions for solid-phase synthesis. The dual linker allows simple evaluation of cleavage rate of polymer-supported compounds from the linker and, at the same time, ensures that all resin-bound components are cleaved from the solid support. The dual linker 4 was assembled from two Wang linkers connected by a three carbon spacer. The linker 9 was synthesized using the PAL and HMPB linkers.

An expedient and convenient approach for one-pot synthesis of 1H-isoindole-1,3(2H)-diones

An easy and expedient method for the one-pot synthesis of 1H-isoindole-1,3(2H)-diones has been developed by the reaction of the corresponding cyclic anhydrides with guanidinium chloride as a nitrogen source in the presence of FeCl3 as a catalyst under mild reaction conditions.

Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines

An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions and excellent substrate generality give this protocol broad application prospects.

Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea

N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.