3-AMINOPHTHALIC HYDRAZIDE
3-Aminophthalhydrazide
CAS: 521-31-3
Molecular Formula: C8H7N3O2
3-AMINOPHTHALIC HYDRAZIDE - Names and Identifiers
| Name | 3-Aminophthalhydrazide |
| Synonyms | Luminol AURORA KA-3798 RARECHEM AH BS 0053 3-AMINOPHTHALHYDRAZINE 3-Aminophthalhydrazide LABOTEST-BB LT00645356 3-AMINOPHTHALHYDRAZIDE 3-AMINOPHTHALIC HYDRAZIDE 3-AMINOPHTHALOYLHYDRAZINE 2,3-Dihydro-5-nitro-4-phthalazinedione 5-AMINO-2,3-DIHYDRO-1,4-PHTHALAZINEDONE 5-Amino-2,3-dihydro-1,4-phthalazinedione 5-AMINO-2,3-DIHYDRO-1,4-PHTHALAZINEDIONE 5-AMINO-2,3-DIHYDRO-PHTHALAZINE-1,4-DIONE 5-amino-1,2,3,4-tetrahydrophthalazine-1,4-dione 5-AMINO-1,2,3,4-TETRAHYDRO-1,4-PHTHALAZINEDIONE 5-amino-2,3-dihydro-1,4-*phthalazinedione free ac |
| CAS | 521-31-3 |
| EINECS | 208-309-4 |
| 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) |
| InChIKey | HWYHZTIRURJOHG-UHFFFAOYSA-N |
3-AMINOPHTHALIC HYDRAZIDE - Physico-chemical Properties
| Molecular Formula | C8H7N3O2 |
| Molar Mass | 177.16 |
| Density | 1.3393 (rough estimate) |
| Melting Point | >300 °C (lit.) |
| Boling Point | 309.07°C (rough estimate) |
| Water Solubility | <0.1 g/100 mL at 19 ºC |
| Solubility | Soluble in lye, soluble in dilute acid, insoluble in water and organic solvents, insoluble in alcohol. When neutral or lightly acidic solutions are exposed to ultraviolet light, they show strong bright blue fluorescence. |
| Appearance | Crystalline powder |
| Color | Dark green to dark blue-purple |
| Maximum wavelength(λmax) | ['425nm'] |
| Merck | 14,5600 |
| BRN | 383929 |
| pKa | (Calcd.) 10.50 ± 0.20;;0.58 ± 0.20(at 25℃) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, strong bases, strong reducing agents. Emits light on reaction with oxidizers. |
| Sensitive | Sensitive to air |
| Refractive Index | 1.6500 (estimate) |
| MDL | MFCD00006890 |
| Physical and Chemical Properties | Yellow crystalline powder. Soluble in alkali, soluble in dilute acid, almost insoluble in water, insoluble in alcohol. When a neutral or slightly acidic solution is exposed to ultraviolet light, it shows strong bright blue fluorescence. Melting point 329-332 ℃ |
| Use | Chemiluminescent analysis detection reagent (e. G. Determination of metal cations or blood) |
3-AMINOPHTHALIC HYDRAZIDE - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S37/39 - Wear suitable gloves and eye/face protection S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | TH8890060 |
| FLUKA BRAND F CODES | 10-23 |
| TSCA | Yes |
| HS Code | 29339990 |
3-AMINOPHTHALIC HYDRAZIDE - Reference
| Reference Show more | 1. Zhang Kaidi, Zengzhi, Zeng Xiangyu, et al. Reliability of single-plane EWOD devices in chemiluminescence detection [J]. Fudan Journal (Natural Science) 2015 54(006):721-727. 2. Meng Qingyu, Fu Ling, Gao Zhen, yin fen, Yao Hanchun, Bi Yuefeng. Comparison of extraction methods and antioxidant activity of total flavonoids from Chrysanthemum indicum [J]. Chinese Herbal Medicine, 2015,46(21):3194-3197. 3. Yao, Hong, et al. "DPPH ·-luminol chemilution system and its application in the determination of scutellarin in pharmaceutical injections and rat plasma with flow injection analysis." Luminal 32.4 (2017): 588-595.https:// doi.org/10.1002/bio.3225 4. Yao, Hong, et al. "A strategy for integrated pharmacokinetic study of cardiovascular herbal medicines based on chemiluminescence and HPLC-MS/MS assays: a case using Danshen injection." RSC advances 7.22 (2017): 13570-13583. 5. [IF=3.361] Hong Yao et al."A strategy for integrated pharmacokinetic study of cardiovascular herbal medicines based on chemiluminescence and HPLC-MS/MS assays: a case using Danshen injection."Rsc Adv. 2017 Feb;7(22):13570-13583 6. [IF=2.464] Hong Yao et al."DPPH·-luminol chemiluminescence system and its application in the determination of scutellarin in pharmaceutical injections and rat plasma with flow injection analysis."Luminescence. 2017 Jun;32(4):588-595 7. [IF=4.616] Zheng Yao et al."Full-color emissive carbon-dots targeting cell walls of onion for in situ imaging of heavy metal pollution."Analyst. 2019 May;144(11):3685-3690 |
3-AMINOPHTHALIC HYDRAZIDE - Introduction
Luminol is one of the oldest and most commonly used reagents. It can be oxidized by peroxides under alkaline conditions and emit light at the same time. The redox reaction between luminol and peroxides requires a catalyst. This catalyst is generally polyvalent metal ions, peroxidase such as iron, horseradish peroxidase, etc. This method is often used to detect the content of peroxides, heavy metals, and peroxidase, as well as the derived methods for detecting free radicals, performing toxicological analysis and analysis based on peroxidase and glucose oxidase. Under normal circumstances, luminol reacts very rapidly with hydrogen peroxide in the presence of some catalysts. The most commonly used catalyst is metal ions. In a large concentration range, the concentration of metal ions is proportional to the luminous intensity, so that the chemiluminescence analysis of certain metal ions can be performed. This reaction can be used to analyze those organic compounds containing metal ions. High sensitivity. Secondly, the inhibition effect of organic compounds on luminol chemiluminescence reaction was used to determine the organic compounds with quenching effect on chemiluminescence reaction. The third is the indirect determination of inorganic or organic compounds through coupling reactions.
Last Update：2022-10-16 17:25:50
3-AMINOPHTHALIC HYDRAZIDE - Reference Information
| pH indicator color change ph range | NonH uorescence (6.0) to blue H uorescence (7.0) |
| main applications | Night vision devices, identification of product forgeries, determination of nitride in food, analytical chemistry, pharmaceuticals, iodine in biological materials, evaluating phagocytes, detecting tumors, DNA, biosensors, assay of fungi, bacteria, yeasts, assay of lipase activity |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Chemical fluorescent molecule | Luminol is a chemical fluorescent molecule that can be converted into excited amino phthalic acid in the presence of hydrogen peroxide molecules, The latter emits strong fluorescence. Hydrogen peroxide is the product of many biological oxidation reactions, so it is easy to link these biological oxidation reactions to light detection by the introduction of luminol. For example, the glucose oxidase/catalase probe can detect the concentration of hydrogen peroxide or glucose in the sample, and the response time is only 0. 5S (dynamic method). The chemiluminescent substance is combined with immunological reaction, and the concentration of the measured immune component is expressed by light reaction, which is called chemiluminescence immunoassay (CLIA). In 1976, Shmeder proposed chemiluminescence immunoassay, using luminol-H202 and the derivative ABEI as the detection reaction display system. At present, luminol (luminol) and its derivatives are the most commonly used markers in chemiluminescence immunoassay applications. Under alkaline conditions, they can release a large number of photons through microperoxidase (microperoxidase) catalysis, lumino can be used for Western Blot of HRP-labeled antibodies and nucleic acid hybridization detection of HRP-labeled probes, as well as for modern criminal bloodstain detection. The compounds of chemiluminescent substances that can be used as chemiluminescent markers must meet the following conditions: high quantum yield of luminescence; its physical and chemical properties match the studied system; its luminescence reaction is the result of the oxidation reaction of luminescent substances; It is non-toxic to organisms within the concentration range used. Several types of chemiluminescent reagents commonly used are: acridine ester (acridinium ester), which is a widely used chemiluminescent tracer. It is a tricyclic organic compound that is easy to oxidize, and the oxidation reaction does not require a catalyst. Photons are released at 430nm; luminol and isiluminol and their derivatives are the most mature chemical luminescent agents. As early as 1964, While made a research report on chemiluminescence, luminol, isoluminol and their derivatives have achieved ideal results for chemiluminescence immunoassay. luminosity detection: the optimum fluorescence wavelength is 400nm (chemical luminosity detection in 60mM K2S2O 8,100mM K2CO3,pH11.5 solution) fig. 1 is luminol structural formula. |
| chemiluminescence method | chemiluminescence method (Chemilum inescence) is widely used as a sensitive measurement method to detect free radicals and reaction metabolites produced in enzymes, cells and biological organisms. The light emitted by its oxidation products and metabolites can be detected by various photometers. Due to its sensitive, rapid, simple operation and low price, chemiluminescence method is widely used in the screening and research of antioxidants, such as polyphenols, polysaccharides, flavonoids, anthraquinones, etc. The chemiluminescence systems commonly used for the determination of superoxide anions include xanthine oxidase-luminol, pyrogallol-luminol and dimethyl sulfoxide-luminol three systems. The former belongs to the enzymatic system, and the latter two belong to the non-enzymatic system. The chemiluminescence systems for the determination of hydroxyl radicals mainly include copper sulfate-yeast (or bone marrow cells)-ascorbic acid-hydrogen peroxide, CuCl-H2O2-o-phenanthroline-carbonate buffer, copper sulfate-o-phenanthroline-ascorbic acid-hydrogen peroxide, ferrous sulfate-luminol-hydrogen peroxide and ferrous sulfate-luminol Five chemiluminescence systems, all involve the classic Fenton reaction to produce hydroxyl radicals, and then attack the luminescent agent to produce chemiluminescence, it can be used to measure the activity of the extract to scavenge reactive oxygen radicals. experimental method: pyrogallol-luminol chemiluminescence system was adopted: luminol was prepared into a solution with a concentration of 0.05mol/L with 0.05mol/L NaOH solution, stored in a dark place, diluted into a solution of 1mmol/L with double distilled water before use, pyrogallol was prepared into a solution of 0.01mol/L with 1mmol/L HCl, and stored in a refrigerator at 4 ℃, dilute to 16 times 6.25 × 10-4mol/L solution with double distilled water before use. 0.05mol/L pH10.2 Na2CO3-NaHCO3 buffer (containing 0.1mmol/L EDTA) was mixed with 1mmol/L luminol at a volume fraction of 2:1 before the experiment to form a mixture of luminol and carbonate buffer. During the measurement, 10.0 μL (0,0.08,0.4,2 and 10 mg/mL) samples with different concentrations (using the sample buffer as the control) are injected into the luminescence cell, then 6.25 × 10-4mol/L pyrogallol 0.05mL is injected, and finally 0.94mL of luminol and carbonic acid buffer mixture is added to start the reaction (30 ℃), the luminous intensity is counted at intervals of 2 seconds, and the total luminous integral intensity of 300s is measured, the background luminescence intensity is the luminescence value without pyrogallol. there are also chemical fluorescence method, fluorescence spectrometry and NBS-dichlorofluorescein chemiluminescence system for the determination of fluorescence chemiluminescence method, etc., their biggest advantage is high sensitivity. |
| use | as chemical analysis reagent and indicator. chemiluminescence analysis and detection reagents (such as determination of metal cations or blood) used for chemiluminescence analysis, such as metal cations, blood and glucocorticoids luminescence test: Emmax 440 nm (chemiluminescence; 60 mM K2S2O 8, 100 mM K2CO3, pH 11.5; After adding H2O2) chemiluminescence reagents and indicators are commonly used in chemiluminescence analysis, such as metal cations, blood immunity, etc. |
| Production method | 3-nitrophthalic acid is obtained by cyclization and reduction. Add 3-nitrophthalic acid to 8% hydrazine aqueous solution and heat to dissolve the solid. Add ethylene glycol, evaporate excess water in the solution in the evaporator, heat at 215-220 ℃ for 2min, close the heterocyclic ring, and obtain yellow nitro compound after cooling. Cooling, adding 10% sodium hydroxide solution, stirring, adding sodium disulfate, heating to boiling, keeping warm for 5min, adding acetic acid, cooling to make bright yellow product. Leave overnight and filter to get the product. |
| category | toxic substances |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD:>500 mg/kg |
| flammability hazard characteristics | combustible; combustion produces toxic nitrogen oxide smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, mist water |
Last Update：2024-04-09 20:45:29
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