3682-14-2

Usage

Uses

Used in Analytical Chemistry:
4-Aminophthalhydrazide is used as a chemiluminescent agent for detecting and measuring reactive oxygen species (ROS) in various assays. Its chemiluminescent properties allow for the sensitive and accurate detection of ROS, which are essential in understanding various biological processes and disease mechanisms.
Used in Medical Research:
In the field of medical research, 4-Aminophthalhydrazide is used as a diagnostic tool for assessing the immune response of neutrophils. It is particularly useful in neutrophil ROS assays post-infections, such as Yersinia pseudotuberculosis and K. pneumonia, as well as in response to formylated-methionine-leucine-proline. These assays help researchers understand the role of neutrophils in the immune system and their response to different pathogens, which can be crucial in developing new treatments and therapies for various diseases.
Used in Pharmaceutical Industry:
4-Aminophthalhydrazide's chemiluminescent properties also make it a valuable compound in the pharmaceutical industry. It can be used in the development of new drugs and therapies that target ROS-related pathways, as well as in the formulation of diagnostic tools for monitoring the effects of these treatments on the immune system.

Biochem/physiol Actions

4-Aminophthalhydrazide or isoluminol is a chemiluminescent compound that comprises a phthalazine ring. It is more hydrophilic than luminol. Isoluminol is commercially used in a wide variety of in vitro immunoassays and is a chemiluminescence amplifier for studying reactive oxygen species. It is also useful as an electroluminescence (ECL) biosensor and as a probe for rapid microbial detection.

InChI:InChI=1/C8H7N3O2.H2O/c9-4-1-2-5-6(3-4)8(13)11-10-7(5)12;/h1-3H,9H2,(H,10,12)(H,11,13);1H2

Upstream product

• 2518-24-3 3-aminophthalimide 
• 2307-00-8 4-amino-N-methylphthalimide 
• 3676-85-5 4-aminophthalimide 
• 610-22-0 dimethyl 4-nitrophthalate 
• 89-40-7 4-nitrophthalimide 
• 3069-13-4 2,3-diacetyl-2,3-dihydro-phthalazine-1,4-dione 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 610-27-5 4-nitrophthalic acid 
• 3682-19-7 6-nitro-2,3-dihydrophthalazine-1,4-dione 
• 2050-19-3 4-nitrophthalic acid diethyl ester 

Downstream Products

• 107807-39-6 isoluminol isothiocyanate 
• 99-05-8 meta-aminobenzoic acid 

Relevant academic research and scientific papers

A High Selective Chemiluminescent Probe Derived from Iso-luminol Enabling High Sensitive Determination of Ferrous Ions in the Environmental Waters

A new chemiluminescence (CL) reagent named 4-amino-5-thiocyanato-phthalyl-hydrazine (iso-luminol-SCN) is synthesized by the bromide-mediated substitution reaction of iso-luminol with sodium thiocyanate in dimethyl formamide (DMF) at room temperature. Stro

Hydrazine-hydroquinone complex as an efficient solid phase hydrazine donor: High yield synthesis of luminol and isoluminol

Isomeric aminophthalhydrazides, luminol and isoluminol were easily obtained from the corresponding aminoph-thalimides by solid phase hydrazinolysis with the hydrazine-hydroquinone complex in high yields. Synthesis of a novel chemiluminescent agent, a heterocyclic analogue of isoluminol related to aminoimidazolecarboxamide, is also described.

Luminol or isoluminol synthesizing method by one-pot process

The invention discloses a luminol or isoluminol synthesizing method by a one-pot process. The luminol or the isoluminol synthesizing method by the one-pot process includes the steps of 1) enabling 3-nitrophthalic acid or 4-nitrophthalic acid as a starting material to react with urea in an organic solvent to obtain 3-nitrophthalimide or 4-nitrophthalimide; 2) enabling the 3-nitrophthalimide or the 4-nitrophthalimide to react with a hydrazine hydrate aqueous solution to obtain 3-nitrophthalhydrazide or 4-nitrophthalhydrazide; 3) enabling the 3-nitrophthalhydrazide or the 4-nitrophthalhydrazide to react with a reducing agent in the presence of a catalyst to obtain luminol or isoluminol. The luminol or the isoluminol synthesizing method by the one-pot process has the advantages of simplicity, convenience in operation, low cost, high yield and less pollution, and can be applicable to industrialized production.

Method for preparing isoluminol from phthalylhydrazine used as raw material

The invention belongs to the technical field of chemical synthesis and particularly relates to a method for preparing isoluminol from phthalylhydrazine used as a raw material. According to the method for preparing the isoluminol, the phthalylhydrazine is used as the raw material and reacts with an acetylation reagent, and diacetyl phthalylhydrazine is obtained; the diacetyl phthalylhydrazine reacts with a nitroso compound, and nitroso diacetyl phthalylhydrazine is obtained; then nitroso phthalylhydrazine is obtained through a deacetylation reaction; the isoluminol is obtained through a reduction reaction. With the adoption of the method, a large quantity of phthalylhydrazine byproducts in the existing Gabriel amine synthesis method are sufficiently utilized as the raw material, the raw material is cheap and easy to obtain, meanwhile, the synthesis process is simple, reaction conditions are mild, the yield of isoluminol products is higher, reactions are simple to operate, the application range is wider, and industrial production requirements of the products can be fully met.

Cyclic Imides. 16. Hydroxy and Methoxy Derivatives of Aminophthalimide and Phthalhydrazide

Treatment of N-alkyl derivatives of 3,6-dichlorophthalimide and 4,5-dichlorophthalimide with potassium nitrite gave 3-hydroxy-6-nitro- and 4-hydroxy-5-nitrophthalimides.The potassium salts of these phenols were alkylated by dialkyl sulfates.The products were reduced to the 3-amino-6-alkoxy- and 4-amino-5-alkoxyphthalimides, and the fluorescence emission spectra of these products were measured.Hydrazinolysis of the phthalimides in a toulene medium gave phthalhydrazides.The luminescence spectra of several aminophthalhydrazides were measured.The infrared and proton magnetic resonance spectra of these and of some nitrophthalhydrazides were measured and aspects of these spectra characteristic of phthalhydrazides were identified.

CHEMILUMINESCENCE MECHANISM OF CYCLIC HYDRAZIDES SUCH AS LUMINOL IN AQUEOUS SOLUTIONS.

Independently of the mode of oxidation, the first critical intermediate on the chemiluminescent pathway of luminol is a hydroperoxide. Below its pK//a it decomposes into oxygen and the parent hydrazide. At higher pH, the monoanion of the hydroperoxide expels nitrogen and yields a monoprotonated dicarboxylate. The latter is chemiexcited to some extent.