5428-09-1

Basic information

• Product Name: N-ALLYLPHTHALIMIDE
• Synonyms: N-ALLYLPHTHALIMIDE;IFLAB-BB F1799-0016;2-(2-Propenyl)-2H-isoindole-1,3-dione;2-Allyl-1,3-dihydro-2H-isoindole-1,3-dione;2-Allyl-2H-isoindole-1,3-dione;2-Allylisoindoline-1,3-dione;N-(2-Propenyl)phthalimide;2-allyl-1H-isoindole-1,3(2H)-dione
• CAS NO: 5428-09-1
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.19
• Product Categories: Intermediates
• Mol File: 5428-09-1.mol

Chemical Properties

• Melting Point: 68.0 to 72.0 °C
• Boiling Point: 295°C(lit.)
• Flash Point: 129°C
• Appearance: White/Solid
• Density: 1.233g/cm³
• Vapor Pressure: 0.00145mmHg at 25°C
• Refractive Index: 1.591
• Storage Temp.: 2-8°C
• PKA: -2.18±0.20(Predicted)
• CAS DataBase Reference: N-ALLYLPHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ALLYLPHTHALIMIDE(5428-09-1)
• EPA Substance Registry System: N-ALLYLPHTHALIMIDE(5428-09-1)

Safety Data

• Hazardous Substances Data: 5428-09-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-Allylphthalimide is used as a reagent for the preparation of allylic amines, which are important intermediates in the synthesis of various organic compounds. Its ability to effectively allylate a range of nucleophiles makes it a valuable component in this application.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, N-Allylphthalimide is utilized in the synthesis of various compounds, contributing to the development of new drugs and therapeutic agents. Its role in creating complex molecular structures is essential for advancing medicinal chemistry.
Used in Natural Product Synthesis:
N-Allylphthalimide also plays a part in the synthesis of natural products, aiding researchers and chemists in replicating or modifying the structures of naturally occurring substances for use in various applications, including medicine and cosmetics.
Used in Research and Development:
Due to its reactivity and versatility, N-Allylphthalimide is employed in research and development settings to explore new chemical reactions and pathways, potentially leading to the discovery of novel compounds and materials.

InChI:InChI=1/C11H9NO2/c1-2-7-12-10(13)8-5-3-4-6-9(8)11(12)14/h2-6H,1,7H2

Upstream product

• 85-44-9 phthalic anhydride 
• 107-11-9 1-amino-2-propene 
• 67-56-1 methanol 
• 71-43-2 benzene 
• 201230-82-2 carbon monoxide 
• 583-53-9 2,3-dibromobenzene 
• 7223-50-9 N-propargylphthalimide 

Downstream Products

• 947-81-9 N-allyl-phthalamic acid 
• 133787-08-3 α-N-benzoyl-δ-N-phthaloylornithine methyl ester 
• 83665-62-7 (E)-2-(3-(4-nitrophenyl)allyl)isoindoline-1,3-dione 
• 128425-78-5 2-allyl-3-hydroxy-3-phenyl-2,3-dihydro-isoindol-1-one 
• 17480-07-8 2-[(E)-3-phenylprop-2-enyl]-2,3-dihydro-1H-isoindole-1,3-dione 
• 22621-98-3 (E)-2-(3-(4-chlorophenyl)allyl)isoindoline-1,3-dione 
• 83680-96-0 N-(para-coumaryl)phthalimide 
• 83665-58-1 (E)-2-(3-(4-bromophenyl)allyl)isoindoline-1,3-dione 
• 83665-89-8 2-[(Z)-3-(2-Chloro-phenyl)-allyl]-isoindole-1,3-dione 
• 83665-59-2 (E)-2-(3-(2-chlorophenyl)allyl)isoindoline-1,3-dione 
• 83665-63-8 N-<4-(thiomethyl)cinnamyl>phthalimide 
• 83665-66-1 (E)-4-(3-(1,3-dioxoisoindolin-2-yl)prop-1-enyl)benzonitrile 
• 83665-65-0 methyl (E)-4-(3-(1,3-dioxoisoindolin-2-yl)prop-1-en-1-yl)benzoate 
• 83665-61-6 2-[(E)-3-(4-Dimethylamino-phenyl)-allyl]-isoindole-1,3-dione 

Relevant articles and documents

Synthesis and pharmacological characterization of new silicon-based W84-type allosteric modulators for ligand binding to muscarinic M2 receptors

The silicon-based allosteric modulators of ligand binding to muscarinic acetylcholine receptors [R1- (CH2) 3-SiMe2-(CH2)5 -NMe2-(CH2)3- R1]Br (3), [R2-(CH2)3 -SiMe2-(CH2)5- NMe2-(CH2)3-R2] Br (4), [R1-(CH2)3- SiMe2-(CH2)5- NMe2-(CH2)3-R2] Br (5), and [R2-(CH2)3- SiMe2-(CH2)5- NMe2-(CH2)3-R1] Br (6) (R1=phthalimido; R2=1,8-naphthalimido) were synthesized, starting from chlorodimethylsilane. Compounds 3-6 were studied for their allosteric interaction at porcine heart muscarinic M2 receptors. They inhibited the dissociation of the orthosteric ligand [3H] N-methylscopolamine ([3H] NMS) with similar potency; compounds 4 and 6 yielded steep concentration-effect curves. All compounds enhanced [3H]NMS equilibrium binding, but with different efficacies. The effect of 4 on [3H]NMS binding was studied at cloned M1-M 5 receptor subtypes. Compound 4 did not affect [3H] NMS equilibrium binding at M1, M3, M4, and M5 receptors, thus representing an M2-selective allosteric enhancer of [3H]NMS binding.

Selective Semi-Hydrogenation of Terminal Alkynes Promoted by Bimetallic Cu-Pd Nanoparticles

The selective semi-hydrogenation of terminal alkynes was efficiently performed, under mild reaction conditions (H 2 balloon, 110 °C), promoted by a bimetallic nanocatalyst composed of copper and palladium nanoparticles (5:1 weight ratio) supported on mesostructured silica (MCM-48). The Cu-PdNPS@MCM-48 catalyst, which demonstrated to be highly chemoselective towards the alkyne functionality, is readily prepared from commercial materials and can be recovered and reused after thermal treatment followed by reduction under H 2 atmosphere.

Synthesis of Branched Triubiquitin Active-Site Directed Probes

Active-site directed probes are powerful tools for studying the ubiquitin conjugation and deconjugation machinery. Branched ubiquitin chains have emerged as important proteasome-targeting signals for aggregation-prone proteins and cell cycle regulators. By implementing a new synthetic strategy for the electrophilic warhead, we herein report on the generation and reactivity of a series of branched triubiquitin active-site directed probes. These new tools can be used to dissect the molecular basis of branched chain assembly and disassembly.

Preparation method of modified silane coupling agent

A preparation method of a modified silane coupling agent comprises: (1), dissolving mono-anhydride or tetracid dianhydride in glacial acetic acid, adding allylamine according to a molar ratio of the mono-anhydride or tetracid dianhydride to the allylamine being 1:1 or 1:2, stirring and reflowing for 3-24 h, adding water, filtering, washing, and drying to obtain an imide product; (2), dissolving the imide product in an aprotic solvent of medium polarity, adding 0.2 ml or 0.35 ml of a catalyst and trialkoxysilane according to a molar ratio to the imide product being 1:1 or 2:1, and reacting at 50-70 DEG C for 5-48 h, distilling at reduced pressure to remove a low-boiling-point fraction to obtain a product.Least catalyst is used at the premise of ensuring optimal catalytic efficiency so that lowest production cost is achieved.

Rhodium/Yanphos-Catalyzed Asymmetric Interrupted Intramolecular Hydroaminomethylation of trans-1,2-Disubstituted Alkenes

The first interrupted asymmetric hydroaminomethylation reaction was developed. The challenging trans-1,2-disubstituted olefins were employed as substrates, and a series of valuable chiral pyrrolidinones and pyrrolidines were obtained in high yields with high regioselectivities and excellent enantioselectivities. Several synthetic transformations were conducted, demonstrating the high synthetic utility of our method. A creative route for the synthesis of vernakalant and Enablex was also developed.

A double-end amino (poly) method for the preparation of

A double-end amino (poly) silicone preparation method, which is characterized in that: the olefin-based primary amine and aromatic or aliphatic formed in ice of phthalic anhydride in acetic acid solvent, for 0 o C-10 o C reaction 1-3h, reflux 3-6h, water, precipitated N-olefin-imide; the molar ratio of 1 : 2.0-5.0 of siloxane and including hydrogen base N-olefin-imide, the aromatic hydrocarbon or alcohol, ether solvent, the presence of a platinum catalyst, for 30 o C-120 o C reaction 3-10h, cooling to room temperature, filter, pressure reducing evaporate the solvent, get [...] imide silicone; the double-phthalimide siloxane dissolved in organic solvent, under the acid catalysis and D 3 or D 4 for 30 o C-100 o C reaction to obtain [...] imide silicone; the double-phthalimide (poly) silicone using ethanol as the solvent, by adding hydrazine hydrate in 60 o C-80 o C reaction 5-15h, filter, pressure reducing evaporate solvent. The process of the invention is simple, normal pressure reaction, non-corrosive material, with little investment; all yield and purity of the product is very high; the solvent can be recycled, the production cost is low, no environmental pollution; by-product of phthalic hydrazide also can be widely applied.

Versatile and sustainable synthesis of cyclic imides from dicarboxylic acids and amines by Nb2O5 as a base-tolerant heterogeneous lewis acid catalyst

Catalytic condensation of dicarboxylics acid and amines without excess amount of activating reagents is the most atom-efficient but unprecedented synthetic method of cyclic imides. Here we present the first general catalytic method, proceeding selectively and efficiently in the presence of a commercial Nb2O5 as a reusable and base-tolerant heterogeneous Lewis acid catalyst. The method is effective for the direct synthesis of pharmaceutically or industrially important cyclic imides, such as phensuximide, N-hydroxyphthalimide (NHPI), and unsubstituted cyclic imides from dicarboxylic acid or anhydrides with amines, hydroxylamine, or ammonia.

Multimetallic iridium-tin (Ir-Sn3) catalyst in N-acyliminium ion chemistry: Synthesis of 3-substituted isoindolinones via intra- and intermolecular amidoalkylation reaction

The multimetallic iridium-tritin (Ir-Sn3) complex [Cp*Ir(SnCl3)2{SnCl2(H2O) 2}] (1) proved to be a highly effective catalyst towards C-OH bond activation of γ-hydroxylactams, leading to a nucleophilic substitution reaction known as the α-amidoalkylation reaction. Catalyst 1 can be easily synthesized from the reaction of (pentamethylcyclocyclopentadienyl)iridium dichloride dimer {[Cp*IrCl2]2} and tin(II) dichloride (SnCl2). In terms of catalyst loading, reaction conditions and yields of the product formed, 1 is found to be superior compared to classical Lewis acid catalysts. Different carbon (arenes, heteroarenes, allyltrimethylsilane, 1,3-dicarbonyls) and heteroatom (alcohols, thiols, amides and sulfonamides) nucleophiles have been successfully employed in the intramolecular and intermolecular alkylations, as well as in heterocyclization reactions. In the majority of cases good to excellent yields of 3-substituted isoindolinones and 5-substituted pyrrolidin-2-ones have been obtained. Besides, the reactions are also atom economical and salt free. It is proposed that the multimetallic Ir-Sn3 catalyst behaves as a mild and selective Lewis acid to activate the γ-hydroxylactam towards the formation of the N-acyliminium ion; the latter being trapped by potent nucleophiles leading to the desired products.

Expeditious synthesis of 1-substituted taurines with diverse functionalized side-chains

A radical addition reaction and subsequent performic acid oxidation were used for the synthesis of 1-substituted taurines with diverse functionalized side-chains from N-allylphthalimide and various xanthates. The current approach shows high yields and short synthetic route and reaction time. Moreover, the current method is a convenient and practical method for the synthesis of 1-substituted taurines with different functionalized side-chains.

Substrate-directable heck reactions with arenediazonium salts. The regio- and stereoselective arylation of allylamine derivatives and applications in the synthesis of naftifine and abamines

The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the car-bonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.