3676-85-5

Usage

Uses

Used in Research Applications:
4-Aminophthalimide is used as a fluorescent labeling compound in research for its ability to emit light when exposed to specific wavelengths. This property allows it to be utilized in various fields, such as biochemistry, molecular biology, and cell biology, to label and track specific molecules or cellular components.
Used in Chemical Synthesis:
In addition to its use in research, 4-Aminophthalimide can also be employed as an intermediate in the synthesis of various chemical compounds. Its unique structure and reactivity make it a versatile building block for creating a range of products, including pharmaceuticals, dyes, and other specialty chemicals.
Used in Analytical Chemistry:
4-Aminophthalimide's fluorescent properties can be harnessed in analytical chemistry for the detection and quantification of specific substances. It can be used to develop sensitive and selective assays, which are crucial for identifying and measuring target analytes in complex samples.
Used in Material Science:
The unique optical properties of 4-Aminophthalimide also make it a candidate for use in the development of advanced materials, such as light-emitting diodes (LEDs), sensors, and other optoelectronic devices. Its potential applications in this field are still being explored and could lead to innovative technologies in the future.

InChI:InChI=1/C8H6N2O2/c9-4-1-2-5-6(3-4)8(12)10-7(5)11/h1-3H,9H2,(H,10,11,12)

Upstream product

• 89-40-7 4-nitrophthalimide 
• 136918-14-4 phthalimide 
• 610-27-5 4-nitrophthalic acid 

Downstream Products

• 107942-71-2 5-(4-hydroxy-phenylazo)-isoindoline-1,3-dione 
• 10506-95-3 N-(1,3-dioxoisoindolin-5-yl)acetamide 
• 49545-91-7 N-(1,3-dioxoisoindolin-5-yl)benzamide 
• 7147-90-2 4-chlorophthalimide 
• 2021-26-3 5-phenylisoindoline-1,3-dione 
• 65399-05-5 5-amino-3H-isobenzofuran-1-one 
• 55080-55-2 4-amino-N-ethylphthalimide 
• 68930-97-2 4-amino-N-butylphthalimide 

Relevant academic research and scientific papers

Development of three ways molecular logic gate based on water soluble phenazine fluorescent ‘selective ion’ sensor

New hydrophilic fluorescent selective ion sensor based on phenazine and phthalazine moieties, 1,1′-(phenazine-2,3-diyl)-bis(3-(1,4-dihydroxyphthalazin-6-yl)urea) (1), has been designed, synthesized and characterized. Interestingly, sensor 1 exhibits prominent “turn-on” and “turn-off” fluorogenic signaling at 580 nm towards Fe2+ & AcO? and Sr2+ & Cu2+, respectively. The fluorescence titration experiments shed light on the nature of the interaction between 1 and guest molecules (Fe2+, Sr2+, Cu2+ and AcO?), which divulge that 1 is flexible enough to orient itself according to the size of the guest molecule. Water mediated excited-state intramolecular proton transfer (ESIPT) and photo-induced electron transfer (PET) mechanisms are responsible for the dual behavior of 1, which binds with guest molecules in 1:1 stoichiometry. Based on the significant duplex fluorescence response of 1, a molecular logic gate keypad lock with sixteen “on” passwords for a storage system has been developed.

Novel n-channel organic semiconductor based on pyrene-phenazine fused monoimide and bisimides

Large π-conjugated pyrene-phenazine monoimide and bisimides were synthesized by imine condensation reaction. These imides form well ordered 1D nanotapes upon self-assembly in solution. Electrochemical and electric conductivity measurement reveal it can be served as an n-channel semiconductor with large charge carrier mobility up to 4.1 cm2 V?1 s?1. Both alkylated imides are highly luminescent, and can be quenched via protonization using trifluoroacetic acid, which could be served as potential colorimetric acid sensors.

Phthalimide compound as well as preparation method and application thereof

The invention provides a phthalimide compound or a pharmaceutically acceptable salt thereof, wherein the structure of the phthalimide compound is shown as a formula I; in the formula I, R1 is selected from hydrogen, aliphatic hydrocarbon, alkoxy and halogen; R2 and R3 are the same or different and are selected from hydrogen, aliphatic hydrocarbon, alkoxy and halogen; or R2, R3 and connected N atoms are cyclized to form a closed substituted or unsubstituted five-membered or six-membered ring; R1, R2 and R3 can be unsubstituted or substituted by straight chain or branched chain alkyl or alkoxy selected from C1 - C10 and halogen; and R1, R2 and R3 are not hydrogen at the same time. The compound disclosed by the invention has the effect of a ROCK inhibitor and an anti-tumor effect, and is expected to be used as a clinical medicine with a relatively high therapeutic index.

Hydrogenation of nitroarenes to anilines in a flow reactor using polystyrene supported rhodium in a catalyst-cartridge (Cart-Rh@PS)

The present methodology described the chemo-selective hydrogenation of various nitroarenes in a flow reactor under polystyrene supported rhodium in a catalyst-cartridge (Cart-Rh@PS) as a heterogeneous nano-catalyst. The polystyrene supported Rh (Rh@PS) nanoparticles (NPs) were prepared by following our earlier reported protocol and packed inside the catalyst-cartridge (Cat-Cart) to obtain Cart-Rh@PS, which is compatible with ThalesNano's H-Cube Pro flow system. The advantages of the prepacked catalyst Cart-Rh@PS are as follows: no need for catalyst activation up to 12 runs, negligible metal leaching detected by ICP-AES analysis and significantly less back pressure generated under the flow conditions. The same catalyst, Cart-Rh@PS, was also effective up to a 1 gram scale for the reduction of nitroarenes and reusable for successive runs. The hydrogenation in the flow reactor is a greener approach for the reduction of nitroarenes to their corresponding anilines in high yields.

Mechanochemical catalytic transfer hydrogenation of aromatic nitro derivatives

Mechanochemical ball milling catalytic transfer hydrogenation (CTH) of aromatic nitro compounds using readily available and cheap ammonium formate as the hydrogen source is demonstrated as a simple, facile and clean approach for the synthesis of substituted anilines and selected pharmaceutically relevant compounds. The scope of mechanochemical CTH is broad, as the reduction conditions tolerate various functionalities, for example nitro, amino, hydroxy, carbonyl, amide, urea, amino acid and heterocyclic. The presented methodology was also successfully integrated with other types of chemical reactions previously carried out mechanochemically, such as amide bond formation by coupling amines with acyl chlorides or anhydrides and click-type coupling reactions between amines and iso(thio)cyanates. In this way, we showed that active pharmaceutical ingredients Procainamide and Paracetamol could be synthesized from the respective nitro-precursors on milligram and gram scale in excellent isolated yields.

4-aminophthalimide synthesis method

The invention provides a 4-aminophthalimide synthesis method which includes the steps: (1) adding dehydrate stannic chloride into concentrated hydrochloric acid, stirring mixture to completely be dissolved, adding 4-nitrophthalimide, stirring and reacting mixture for 0.5-60 hours at the temperature of 40-80 DEG C, and stopping reaction; (2) extracting and filtering reaction liquid to obtain filterresidues, soaking the filter residues by the aid of the concentrated hydrochloric acid twice, drying the filter residues, soaking the filter residues by the aid of ethyl acetate twice, performing second extracting and filtering, drying filter residues acquired after the second extracting and filtering to obtain 4-aminophthalimide. According to the method, excessive reducing agent purification products after reaction can be effectively removed, a post-treating process can be simplified, cost is reduced, and the yield and the purity of the products are high.

Preparation method of novel isobenzofuranone intermediate

The invention discloses a synthetic method of an important intermediate of novel diuretic drug ROMK inhibitor. The synthetic method comprises the following steps: adopting 4-nitro phthalimide as the starting material, performing two-step reaction, diazotization reaction, Suzuki reaction and epoxidation reaction, thus obtaining the important intermediate 5-epoxy ethyl isobenzofuranone of the ROMK inhibitor. The preparation method provided by the invention is mild in route reaction conditions, simple in after-treatment, high in yield, and capable of avoiding the use of toxic gases and bioenzymecatalysts.

Chemoselective Hydrogenation of Nitroarenes Catalyzed by Molybdenum Sulphide Clusters

Herein, we describe an atom efficient and general protocol for the chemoselective hydrogenation of nitroarenes to anilines catalyzed by well-defined diimino and diamino cubane-type Mo3S4 clusters. The novel diimino [Mo3S4Cl3(dnbpy)3]+ ([5]+) (dnbpy=4,4′-dinonyl-2,2′-dipyridyl, L1) trinuclear complex was synthesized in high yields by simple ligand substitution reactions starting from the thiourea (tu) [Mo3S4(tu)8(H2O)]Cl4?4 H2O (3) precursor. This strategy has also been successfully adapted for the isolation of the diamino [Mo3S4Cl3(dmen)3](BF4) ([6](BF4)), (dmen=N,N′-dimethylethylenediamine) salt. Applying these catalysts, high selectivity in the hydrogenation of functionalized nitroarenes has been accomplished. Over thirty anilines bearing synthetically functional groups have been synthesized in 70 to 99 % yield. Notably, the integrity of the cluster core is preserved during catalysis. Based on kinetic studies on the hydrogenation of nitrobenzene and other potential reaction intermediates, the direct reduction to aniline is the preferential route.

Isoindol - 1, 3 - dione compound and its preparation method and application (by machine translation)

The invention discloses a isoindole - 1, 3 - dione compound and its preparation method and application. The general formula (I) has the structure shown. The invention of the isoindole - 1, 3 - diones to LNCap cells with cell inhibitory activity, can be used for preparing anti-tumor drug. (by machine translation)

Ni@Pd core-shell nanoparticles supported on a metal-organic framework as highly efficient catalysts for nitroarenes reduction

Ni@Pd core-shell nanoparticles with a mean particle size of 8-9 nm were prepared by solvothermal reduction of bivalent nickel and palladium in oleylamine and trioctylphosphine. Subsequently, the first-ever deposition of Ni@Pd core-shell nanoparticles having different compositions on a metal-organic framework (MIL-101) was accomplished by wet impregnation in n-hexane. The Ni@Pd/MIL-101 materials were characterized by powder X-ray diffraction, Fourier transform infrared spectroscopy, transmission electron microscopy, and energy-dispersive X-ray spectroscopy and also investigated as catalysts for the hydrogenation of nitrobenzene under mild reaction conditions. At 30 °C and 0.1 MPa of H2 pressure, the Ni@Pd/MIL-101 gives a TOF as high as 375 h-1 for the hydrogenation of nitrobenzene and is applicable to a wide range of substituted nitroarenes. The exceptional performance of this catalyst is believed to result from the significant Ni-Pd interaction in the core-shell structure, together with promotion of the conversions of aromatics by uncoordinated Lewis acidic Cr sites on the MIL-101 support.