521-31-3

Basic information

• Product Name: 3-Aminophthalhydrazide
• Synonyms: AURORA KA-3798;LABOTEST-BB LT00645356;LUMINOL;3-AMINOPHTHALHYDRAZINE;3-AMINOPHTHALIC HYDRAZIDE;3-AMINOPHTHALOYLHYDRAZINE;3-AMINOPHTHALHYDRAZIDE;5-AMINO-2,3-DIHYDRO-PHTHALAZINE-1,4-DIONE
• CAS NO: 521-31-3
• Molecular Formula: C₈H₇N₃O₂
• Molecular Weight: 177.16
• EINECS: 208-309-4
• Product Categories: Piperazine derivates;Analytical Chemistry;Chemiluminescence;Luminols (Chemiluminescence);Pharmaceutical intermediates;Fluorescent
• Mol File: 521-31-3.mol

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 309.07°C (rough estimate)
• Flash Point: 329.9oC
• Appearance: Dark green to dark blue-purple/Powder
• Density: 1.3393 (rough estimate)
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Solubility Insoluble in water, soluble in dimethyl sulfoxide, ba
• PKA: (Calcd.) 10.50 ± 0.20;;0.58 ± 0.20(at 25℃)
• Water Solubility: <0.1 g/100 mL at 19℃
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, strong bases, strong reducing agents. Emits light
• Merck: 14,5600
• BRN: 383929
• CAS DataBase Reference: 3-Aminophthalhydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminophthalhydrazide(521-31-3)
• EPA Substance Registry System: 3-Aminophthalhydrazide(521-31-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-20/21/22
• Safety Statements: 26-36/37-37/39-36
• WGK Germany: 3
• RTECS: TH8890060
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 521-31-3(Hazardous Substances Data)

Usage

Chemical fluorescent molecules

Luminol?is an organic compound which, when oxidized, emits light — a phenomenon known as?chemiluminescence.??This is similar to the reactions that fireflies uses to emit light, and to those used in "glow-sticks" and some roadside emergency lights.?In this reaction, a small amount of luminol?(3-aminophthalhydrazide or 5-amino-2,3-dihydro- 1,4-phthalazinedione) is dissolved in a basic aqueous solution, which also contains a small amount of copper(II) sulfate.? To this solution is added a solution of a mild oxidizing agent, which is 0.3% hydrogen peroxide in the demonstration below.? (Bleach is also used in some recipes as the oxidizing agent.)??The reaction is believed to occur by the following mechanism:

Chemiluminescence method

Luminol chemiluminescence has been trialed for estimating the PMI from skeletal remains. Luminol methods are based on the reaction between luminol and hydrogen peroxide which is catalyzed by iron in hemoglobin found in fluids and tissues from bodies. This reaction results in a chemiluminescence light which can be measured by various means .

Chemical properties

Yellow crystalline powder, Easily soluble in lye, soluble in dilute acid but almost insoluble in water and hardly soluble in alcohol. When its neutral or weak acidic solution is exposed to ultraviolet light, it exhibits strongly bright blue fluorescence. Melting point: 329-332 ° C

Uses

Different sources of media describe the Uses of 521-31-3 differently. You can refer to the following data:
1. 1.??? It can be used as chemical analysis reagents, indicators. 2.??? It can be used for chemiluminescence analysis such as measurement of metal cations, blood and glucocorticoids
2. Luminol is a chemiluminescent probe that has been used to detect myeloperoxidase-mediated oxidative events in granulocytes and for chemiluminescence analysis of metal cations and blood.
3. Detection of copper, iron, peroxides, cyanides.
4. Luminol is used in the detection of copper, iron, peroxides and cyanides. It exhibits chemiluminescence and utilized to measure opsonic and phagocytic function. It acts as a biological sensor and involved in the detection of polymorphonuclear leukocytes response in a patient with a myeloperoxidase deficiency. Further, it is used as a forensic test for blood.

Hazards & Safety Information

Category Toxic substances Toxic grading poisoning Acute toxicity Oral – rat; LD50: > 500 mg/kg Flammability and Hazardous properties it is combustible with combustion producing toxic nitrogen oxide fumes Storage and transportation characteristics warehouse: ventilated, low temperature and dry Fire extinguishing agent dry powder, foam, sand, carbon dioxide, mist water

Chemical Properties

yellow crystals or beige powder

General Description

Yellow crystals or light beige powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Oxidation of 3-Aminophthalhydrazide is accompanied by a striking emission of light. . .

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 3-Aminophthalhydrazide emits toxic fumes.

Fire Hazard

Flash point data for 3-Aminophthalhydrazide are not available, but 3-Aminophthalhydrazide is probably combustible.

Synthesis

The synthesis of Luminol is as follows: To a reaction tube, add 140 mg of 3-nitrophthalhydrazide and 1.0 mL of 3 M sodium hydroxide solution. Stir with a rod, and to the resulting deep brown-red solution add 0.6 g of sodium hydrosulfite dihydrate (Na2S2O4 · 2 H2O, MW 210.2). Wash down the sides of the tube with a small amount of water. Heat to a gentle boil and keep the tube hot for 5 minutes. During this time some product may begin to crystallize. Add 0.4 mL of acetic acid, cool the tube in cold water, and stir. Collect the light-yellow product?Luminol by suction filtration.

Purification Methods

Dissolve luminol in KOH solution, treat with Norit (charcoal), filter and precipitate it with conc HCl. [Hardy et al. Talanta 24 297 1977.] Store it in the dark in an inert atmosphere, because its structure changes during its luminescence. It has been recrystallised from 0.1M KOH [Merenyi et al. J Am Chem Soc 108 77716 1986]. [Beilstein 25 II 389, 25 III/IV 4192.]

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

Upstream product

• 121433-36-1 2,4-diaminoisoindoline-1,3-dione 
• 16533-45-2 ethyl 2-carboxy-3-nitrobenzoate 
• 60851-83-4 5-aminophthalazine-1,4-dione 
• 2518-24-3 3-aminophthalimide 
• 7732-18-5 water 
• 7803-57-8 hydrazine hydrate 
• 2257-85-4 4-amino-2-methyl-1H-isoindole-1,3(2H)-dione 
• 768370-07-6 (2-methyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl)-carbamic acid benzyl ester 
• 603-62-3 4-nitro-1H-isoindole-1,3(2H)-dione 
• 603-11-2 3-nitrophthalic acid 
• 3682-15-3 5-nitro-2,3-dihydro-phthalazine-1,4-dione 

Downstream Products

• 15371-00-3 5-Acetylamino-2-acetyl-phthalaz-1,4-dion 
• 27846-29-3 3-aminophthalate dianion 
• 60851-83-4 5-aminophthalazine-1,4-dione 
• 99-05-8 meta-aminobenzoic acid 
• 54569-56-1 5-(2-chloro-acetylamino)-2,3-dihydro-phthalazine-1,4-dione 
• 554-68-7 triethylamine hydrochloride 
• 1173901-18-2 7-amino-3,4-dihydro-3,3-dimethyl-13-(4-fluorophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione 
• 1173901-16-0 7-amino-3,4-dihydro-3,3-dimethyl-13-(4-methoxyphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione 
• 1173901-24-0 7-amino-3,4-dihydro-3,3-dimethyl-13-(2,4-dichlorophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione 
• 1173901-14-8 7-amino-3,4-dihydro-3,3-dimethyl-13-(4-cyanphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione 
• 1173901-27-3 7-amino-3,4-dihydro-3,3-dimethyl-13-(2-bromophenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione 
• 1173901-22-8 7-amino-3,4-dihydro-3,3-dimethyl-13-(2,3-dimethoxyphenyl)-2H-indazolo[2,1-b]phthalazine-1,6,11(13H)-trione 
• 5434-20-8 3-aminophthalic acid 

Relevant articles and documents

Physico-chemical properties of isomeric forms of luminol in aqueous solutions

Two luminol isomers, 2,4-diaminoisoindoline-1,3-dione and 8-amino-4-hydroxyphthalazin-1(2H)-one, have been obtained and described, their physical and chemical properties studied. Using UV-spectroscopy and fluorescence data, it has been shown that, in aque

A Common, Facile and Eco-Friendly Method for the Reduction of Nitroarenes, Selective Reduction of Poly-Nitroarenes and Deoxygenation of N-Oxide Containing Heteroarenes Using Elemental Sulfur

A transition metal-free, environment-friendly and practical protocol was developed either for the reduction of nitroarenes or for the deoxygenation of N-oxide containing heteroarenes. The reaction proceeded with the use of a non-toxic and cheap feedstock as elemental sulfur in aqueous methanol under relatively mild conditions. Green chemistry credentials were widely favorable compared to traditional and industrial protocols with good E-factors and a low production of waste. The strategy allowed the efficient reduction of a large variety of substituted-nitroarenes including various o-nitroanilines as well as selective reduction of various poly-nitroarenes in excellent yields with a broad substrate scope. The protocol was successfully extended to the deoxygenation of some N-oxide containing heteroarenes, like benzofuroxans, phenazine N,N'-dioxides, pyridine N-oxides, 2H-indazole N1-oxides, quinoxaline N1,N4-dioxides and benzo[d]imidazole N1,N3-dioxides. A gram-scale example for the synthesis of luminol, in green conditions, was reported. A solid mechanism of reaction was proposed from experimental evidences.

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.

CRYSTALLINE FORM OF 5-AMINO-2,3-DIHYDROPHTHALAZINE-1,4-DIONE

A new crystalline form of 5-amino-2,3-dihydro-1,4-phthalazinedione (luminol) is provided. Advantageous uses for this crystalline form as a detecting agent or as an agent for forensic purposes are disclosed, as well a pharmaceutical composition containing said crystalline form.

CRYSTALLINE FORMS FOR 5-AMINO-2, 3-DIHYDROPHTHALAZINE-1, 4-DIONE SODIUM SALT, PHARMACEUTICAL PREPARATIONS CONTAINING THE SAME AND METHOD FOR THE PRODUCTION OF SAID FORMS

The invention relates to the provision of two novel crystalline forms I and II for 5-amino-2,3-dihydrophthalazine-1,4-dione sodium salt. Surprisingly, it was discovered that form I and form II have differing immunological effects. This advantageous property is useful for immunospecific applications. In addition, both forms have advantageous physicochemical properties, which are useful in the production, further processing and/or use of a pharmaceutical preparation of form I or form II or a mixture of both.

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.

On the photophysical properties of new luminol derivatives and their synthetic phthalimide precursors

The photophysical properties of a series of structurally related 4-aminophthalimides and the corresponding 5-aminophthalic hydrazides (luminols) are reported. Absorption, steady-state, and time-resolved fluorescence spectra of luminols exhibited substitution, solvent, and pH dependence. Singlet lifetimes have been determined by time-resolved laser flash spectroscopy. UV spectra in gas phase and DMSO solution were calculated by TD-DFT which revealed the existence of two low-energy excited singlet states with strong pH-sensitivity. Springer Science+Business Media, LLC 2010.

A new efficient synthesis of substituted luminols using multicomponent reactions

A new general synthesis of substituted luminols (5-amino-2,3- dihydrophthalazine-1,4-diones) is presented. Diversely substituted luminol derivatives can be synthesized in three steps. The products are of interest as new materials, which exhibit chemiluminescence.

Composition of matter having bioactive properties

Particles of coordinated complex comprising a basic, hydrous polymer and a capacitance adding compound, as well as methods for their production, are described. These complexes exhibit a high degree of bioactivity making them suitable for a broad range of applications through their incorporation into conventional vehicles benefiting from antimicrobial and similar properties.

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.