3-methyl-1-phenyl-2-pyrazolin-5-on
3-Methyl-1-phenyl-2-pyrazolin-5-one
CAS: 89-25-8
Molecular Formula: C10H10N2O
3-methyl-1-phenyl-2-pyrazolin-5-on - Names and Identifiers
| Name | 3-Methyl-1-phenyl-2-pyrazolin-5-one |
| Synonyms | PMP MCI-186 Edaravone 1,3,5-PMP MONOPYRAZOLONE C.I. Developer 1 TIMTEC-BB SBB003801 1-Phenyl-3-Methyl-5-Pyrazole 3-methyl-1-phenyl-5-pyrazolon 1-Phenyl-3-Methyl-5-Pyrazolone 3-methyl-1-phenyl-2-pyrazolin-5-on 3-Methyl-1-phenyl-2-pyrazolin-5-one 2-Pyrazolin-5-one, 3-methyl-1-phenyl- 3H-Pyrazol-3-one,2,4-dihydro-5-methyl- 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one 2,4-dihydro-5-methyl-2-phenyl-3h-pyrazol-3-on 2,4-dihydro-5-methyl-2-phenyl-3h-pyrazol-3-one |
| CAS | 89-25-8 |
| EINECS | 201-891-0 |
| InChI | InChI=1/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3 |
| InChIKey | QELUYTUMUWHWMC-UHFFFAOYSA-N |
3-methyl-1-phenyl-2-pyrazolin-5-on - Physico-chemical Properties
| Molecular Formula | C10H10N2O |
| Molar Mass | 174.2 |
| Density | 1,12 g/cm3 |
| Melting Point | 126-128°C(lit.) |
| Boling Point | 287°C265mm Hg(lit.) |
| Flash Point | 191°C/17mm |
| Water Solubility | 3 g/L (20 ºC) |
| Solubility | Soluble in hot water, alcohol, acid, alkali, slightly soluble in benzene, insoluble in ether, petroleum ether. |
| Vapor Presure | 0.016Pa at 20℃ |
| Appearance | Pale yellow crystalline powder |
| Color | Yellow to beige |
| Merck | 14,6713 |
| BRN | 609575 |
| pKa | 2.73±0.50(Predicted) |
| PH | 4.0-4.4 (H2O, 20℃)(saturated aqueous solution) |
| Storage Condition | 2-8°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
| Sensitive | Air sensitivity |
| Refractive Index | 1.6300 (estimate) |
| MDL | MFCD00003138 |
| Physical and Chemical Properties | Melting point 127-131°C boiling point 287°C (265 mmHg) water-soluble 3g/L (20°C) |
| Use | Intermediates for the preparation of pyrazolone dyes and pharmaceuticals |
3-methyl-1-phenyl-2-pyrazolin-5-on - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 1 |
| RTECS | UQ9625000 |
| TSCA | Yes |
| HS Code | 29331990 |
| Toxicity | LD50 orl-rat: 3500 mg/kg LONZA# 08FEB79 |
3-methyl-1-phenyl-2-pyrazolin-5-on - Upstream Downstream Industry
3-methyl-1-phenyl-2-pyrazolin-5-on - Reference
| Reference Show more | 1. Xu Chenyu, Song Yingli, Wang Weiqian, Qin Wen, Wang Dan. Determination of mannose in compound capsule of dendrobium officinale [J]. Modern food, 2021(03):145-150. 2. [IF = 2.516] Nani Wang et al."Monosactride composition analysis of immunomodulatory polyaccharides by on‐line holow fiber microextraction with high‐performance liquid chromatography. J Sep Sci. 2016 Mar;39(5):818-826 3. [IF = 7.514] Jing Ma et al." The inhibition of pectin oligosacarides on degranulation of RBL-2H3 cells from apple pectin with high. "Food Chem. 2022 Mar;371:131097 4. [IF = 6.475] Mingchun Wen et al."Quantitative changes in monosaccharides of Keemun black tea and qualitative analysis of theaflavins-glucose adducts during processing."Food Res Int. 2021 Oct;148:110588 5. [IF=3.645] Jiayi Hu et al."Determination and analysis of monosaccharides in Polygonatum cyrtonema Hua polysaccharides from different areas by ultra-high-performance liquid chromatography quadrupole trap tandem mass spectrometry."J Sep Sci. 2021 Sep;44(18):3506-3515 6. [IF=5.165] Hongmei Zhang et al."Quality differentiation method of similar phytomedicines with high sugar content based on the sugar-marker: Taking Schisandrae Chinensis Fructus and Schisandrae Sphenantherae Fructus as an example."Arab J Chem. 2022 Apr;15:103727 7. [IF=5.396] Chunyin Qin et al."Comparison on the chemical composition, antioxidant, anti-inflammatory α-amylase and α-glycosidase inhibitory activities of the supernatant and cream from black tea infusion."Food & Function. 2022 Apr ;: |
3-methyl-1-phenyl-2-pyrazolin-5-on - Nature
Open Data Verified Data
white powder or crystal. Soluble in water, slightly soluble in ethanol or benzene, difficult to dissolve in cold water, petroleum ether, ether. Boiling Point (27. 33kPa)287 ℃. The melting point was 129-130 °c. Vapor pressure (20 °c) <1.33 PA. Refractive index 1.637.
Last Update：2024-01-02 23:10:35
3-methyl-1-phenyl-2-pyrazolin-5-on - Preparation Method
Open Data Verified Data
- using glacial acetic acid as raw material, ketene was obtained by pyrolysis at high temperature, and diketene was obtained by polymerization, followed by ammonolysis to obtain acetoacetamide.
- further, aniline is used as a raw material, and under acidic conditions (hydrochloric acid), diazotization is carried out by using NaN02, and reduction is carried out by using ammonium bisulfite and ammonium sulfite as a reducing agent, followed by hydrolysis with sulfuric acid to produce phenylhydrazine.
- phenylhydrazine and acetoacetamide condensation product.
Last Update：2022-01-01 10:54:07
3-methyl-1-phenyl-2-pyrazolin-5-on - Standard
Authoritative Data Verified Data
This product is 3-methyl -1-phenyl -2-pyrazolin-5-one. The content of C10H10N2O shall not be less than 99.0% based on the dry product.
Last Update：2024-01-02 23:10:35
3-methyl-1-phenyl-2-pyrazolin-5-on - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder; Odorless.
- This product is soluble or soluble in methanol, soluble in ethanol, very slightly soluble or almost insoluble in water.
melting point
The melting point of this product is 126~130 ℃ (General 0612).
Last Update：2022-01-01 13:36:28
3-methyl-1-phenyl-2-pyrazolin-5-on - Introduction
Soluble in water, solubility in water: 3g/l (20°C). Slightly soluble in ethanol and benzene, insoluble in ether, soluble in acid.
Last Update：2022-10-16 17:29:37
3-methyl-1-phenyl-2-pyrazolin-5-on - Use
Open Data Verified Data
mainly used in the production of pharmaceutical antipyrine, aminopyrine, analgin. Also used in dyes (permanent yellow G, acid medium jujube BN, etc.) and color film dyes, pesticides and organic synthesis industry. And can be used as a chemical reagent for detecting vitamin B12,CO,Fe,Cu,Ni, etc.
Last Update：2022-01-01 10:54:06
3-methyl-1-phenyl-2-pyrazolin-5-on - Differential diagnosis
Authoritative Data Verified Data
- take this product 50mg, add ethanol 2ml to dissolve, add 2 drops of bromine test solution, shake, Bromine test solution fade.
- take this product, dissolve and dilute with ethanol to make a solution containing about 8ug per lml, and measure by UV-Vis spectrophotometry (General 0401), there is an absorption maximum at a wavelength of 244Nm.
- The infrared absorption spectrum of this product should be consistent with that of the reference product (General rule 0402).
Last Update：2022-01-01 13:36:29
3-methyl-1-phenyl-2-pyrazolin-5-on - Safety
Open Data Verified Data
- low toxicity, no report of harm. Contact allergy was found in the production process. Inhalation of its vapor will stimulate the respiratory tract, causing chest tightness, Cough, loss of appetite and other symptoms. Skin contact caused by redness and swelling. When out of contact, general symptoms can be disappeared, no sustained effect.
- It is packed with plastic bags, jacket hemp bags or polypropylene woven bags, or external wood barrels, cardboard barrels, etc., each 30kg, 40kg or 50kg. Store in a dry ventilated place. Prevent moisture and heat. According to the general provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:54:08
3-methyl-1-phenyl-2-pyrazolin-5-on - Exam
Authoritative Data Verified Data
acidity
take 0.50g of this product, add 50ml of water, shake for 10 minutes, filter, take the filtrate to determine according to law (General 0631) , pH value should be 4.5~5.5.
clarity and color of ethanol solution
take this product O.lg, add 0901 ethanol to dissolve, the solution should be clear and colorless; If the color is colored, it should not be deeper compared with the yellow or yellow-green No. 1 Standard Colorimetric solution (General Principles first method).
Related substances
new system for clinical use. Take an appropriate amount of this product, add the mobile phase to dissolve and dilute to make a solution containing about 1 mg per 1 ml, as a test solution; Take an appropriate amount of precision I, A solution containing about 1 ug per 1 ml was prepared as a control solution by quantitative dilution with the mobile phase. Test according to high performance liquid chromatography (General 0512). Silica gel bonded with eighteen alkyl silane was used as the filler; The mobile phase was methanol -0.05mol/L ammonium dihydrogen phosphate solution (adjusted to pH 20% with 3.5 phosphoric acid solution)(50:50); The detection wavelength was 245mn. Take an appropriate amount of reference substance of impurity I, add methanol to dissolve and dilute to make a solution containing about 2ug per lml, take lml, add human test solution (lml), mix well, and use as a system applicable solution, measure 10 u1, inject into liquid chromatograph, record chromatogram, the separation degree between edaravone peak and impurity I peak should be greater than 8.0. Take 10 u1 of the test solution and the control solution respectively, inject the human liquid chromatograph, record the chromatogram to 7 times of the retention time of the main component peak. If there is a chromatographic peak consistent with the retention time of impurity I in the chromatogram of the test solution, the peak area shall not be greater than the main peak area of the control solution (0.1% ) , other single impurity peak area shall not be greater than the main peak area of the control solution (0.1% ) , and the sum of each impurity peak area shall not be greater than 3 times (0.3%) of the main peak area of the control solution.
phenylhydrazine
new system for clinical use. Take an appropriate amount of this product, precision weighing, adding mobile phase dissolution and quantitative dilution to make a solution containing about 1 mg per 1 ml, as a test solution; Take an appropriate amount of phenylhydrazine, precision weighing, the mobile phase was added to dissolve and quantitatively dilute to prepare a solution containing about 0.5ug per 1 ml as a control solution. Tested according to high performance liquid chromatography (General 0512). The mobile phase consisted of methanol -0.05mol/L ammonium dihydrogen phosphate solution (adjusted to pH 20% with 3.5 phosphoric acid solution)(25:75) and the detection wavelength was 226nm. 20 u1 of the test solution and the reference solution were respectively injected into the human liquid chromatograph, and the chromatograms were recorded. If there is a chromatographic peak consistent with the retention time of phenylhydrazine peak in the chromatogram of the sample and solution, the peak area shall be calculated according to the external standard method, and shall not exceed 0.05%.
loss on drying
take this product, at 60°C under reduced pressure drying to constant weight, weight loss should not exceed 0.5% (General rule 0831).
ignition residue
about l.Og of this product shall be taken and inspected according to law (General rule 0841). The remaining residue shall not exceed 0.1%.
Heavy metals
The residue left under the item of burning and flooding shall be inspected according to law (general law 0821, Law II) and shall not contain more than 10 parts per million of heavy metals.
Last Update：2022-01-01 13:36:30
3-methyl-1-phenyl-2-pyrazolin-5-on - Content determination
Authoritative Data Verified Data
take this product about 0.32g, precision weighing, add ethanol 60ml, slightly heat to dissolve, cool, according to the potential titration method (General rule 0701), with sodium hydroxide titration solution (O. 1 mol/L) titration, and the results of the titration were corrected with a blank test. Each 1 ml of sodium hydroxide titration solution (0.1 mol/L) corresponds to 17.42mg of C10H10N2O.
Last Update：2022-01-01 13:36:30
3-methyl-1-phenyl-2-pyrazolin-5-on - Category
Authoritative Data Verified Data
free radical scavengers.
Last Update：2022-01-01 13:36:31
3-methyl-1-phenyl-2-pyrazolin-5-on - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 13:36:31
3-methyl-1-phenyl-2-pyrazolin-5-on - Edaravone injection
Authoritative Data Verified Data
This product is a sterile aqueous solution of edaravone. The content of edaravone (C10H10N2O) should be 90.0% to 110.0% of the labeled amount.
trait
This product is a colorless to yellowish (or yellowish green) clear liquid.
identification
- take 2ml of this product, add 1 drop of bromine test solution, shake well, Bromine test solution color.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- This product is diluted with water to prepare a solution containing about 8ug of edaravone per 1 ml, which is determined by UV-visible spectrophotometry (General rule 0401) and has a maximum absorption at the wavelength of 239nm.
examination
- the pH value should be 3.0 to 4.5 (General 0631).
- color this product should be colorless; If the color, and yellow or yellow-green No. 1 Standard Colorimetric liquid (General Principles 0901 The first method) comparison, not deeper.
- appropriate amount of related substances should be taken and diluted with mobile phase to prepare a solution containing about 0.5mg of edaravone per 1 ml as a sample solution, A solution containing about 0.5ug of edaravone per 1 ml was prepared by dilution with the mobile phase as a control solution. According to the chromatographic conditions under the content determination item, 20 u1 of the test solution and the control solution are accurately measured, and the human liquid chromatograph is injected respectively, and the chromatogram is recorded to 7 times of the retention time of the main component peak. If there is a chromatographic peak in the chromatogram of the test solution that is consistent with the retention time of impurity I peak, the peak area shall not be greater than the main peak area of the control solution (0.1%), other single impurity peak area shall not be greater than 6 times (0.6%) of the main peak area of the control solution, and the sum of each impurity peak area shall not be greater than 12 times (1.2%) of the main peak area of the control solution.
- the bacterial endotoxin should be taken and checked according to law (General rule 1143). The amount of endotoxin contained in 1 mg of Edaravone should be less than 2.0EU.
- sterile take this product, after membrane filtration treatment, with PH 7.0 sterile gasification sodium-peptone buffer washing (not less than 200ml per membrane), with Staphylococcus aureus as positive control bacteria, inspection in accordance with the law (General rule 1101), should comply with the provisions.
- others should comply with the relevant provisions under injection (General 0102).
Content determination
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; 0.05mol/L ammonium dihydrogen phosphate solution (adjusted to pH 20% with 3.5 phosphoric acid solution)-methanol (50:50) as mobile phase; The detection wavelength was 245mn. Take the appropriate amount of edaravone and impurity I respectively, add methanol to dissolve and dilute to make a mixed solution containing about 0.5ug in each lml, take 20 u1, and inject human liquid chromatograph, record chromatogram, the separation degree of edaravone peak and impurity I peak should be greater than 8.0.
- determination precision: take an appropriate amount of this product and dilute it with mobile phase to make a solution containing about 50ug of edaravone per lml, as a sample solution, take 20 u1 for precision measurement, and inject it into human liquid chromatograph, record the chromatogram; Take an appropriate amount of edaravone reference substance, precisely weigh, add mobile phase to dissolve and quantitatively dilute to make a solution containing about 50ug per 1 ml, and determine with the same method. According to the external standard method to calculate the peak area, that is.
category
Same as edaravone.
specification
(l)5ml:lOmg (2)10ml:15mg (3)20ml:30mg
storage
light shielding, closed storage.
Last Update：2022-01-01 13:36:32
3-methyl-1-phenyl-2-pyrazolin-5-on - Reference Information
| LogP | 0.75 at 24℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | edaravone is a new free radical scavenger, which was first launched in Japan in April, clinical mainly for the treatment of ischemic stroke. Edaravone exists in the form of anion, and can provide one electron to free radical to achieve the purpose of scavenging free radical. Because its molecular structure contains lipophilic groups, it is easy to reach the brain tissue through the blood-brain barrier, and has a protective effect on nerve cell injury caused by cerebral ischemia. |
| mechanism of action | the protective mechanism of edaravone on nerve cells mainly includes scavenging oxygen free radicals and inhibiting lipid peroxidation, regulation of inflammatory factors, inhibition of apoptosis and so on. With the in-depth study of edaravone, it is found that in addition to the treatment of acute cerebral ischemia, edaravone has therapeutic effect on other diseases involving oxidative stress in the nervous system. In addition, edaravone also has a protective effect on other organs outside the nervous system. At present, Edaravone is mainly used for the treatment of ischemic stroke, but less in other clinical applications. |
| indication | is suitable for improving neurological symptoms, activities of daily living and dysfunction caused by acute cerebral infarction. |
| drug interaction | combined with cefazolin, piperacillin, cefotiam, etc. Mixed with potassium Cantali or antiepileptic drugs such as diazepam, phenytoin sodium can produce turbidity. |
| preparation | a synthetic method of edaravone, comprising the following steps:(1) the hydrochloric acid solution or dilute sulfuric acid solution is cooled to 0~5 ℃ in an ice bath, and aniline solution is added dropwise thereto under stirring conditions. After the dropwise addition is completed, sodium nitrite solution is added dropwise thereto, maintain the temperature at 8~10 ℃, the dropping time is 1H, after the completion of all the dropping, keep the stirring reaction for a period of time, that is, to obtain the diazotization product;(2) step (1) the diazotization product was added dropwise to sodium bisulfite or sodium sulfite solution at 80~85 ℃ for 0.5~1H. After the addition, the mixture was kept for 30min and stirred; then heated reflux reaction for a period of time, and then add hydrochloric acid solution Dropwise, reflux acid after a period of time, to obtain phenylhydrazine hydrochloride;(3) step (2) after the reaction solution was cooled to room temperature, the pH was adjusted to 6 with aqueous ammonia, and ethyl acetoacetate was added dropwise thereto with vigorous stirring. The dropwise addition time was controlled to 1H, heating and refluxing, under the condition of stirring condensation reaction, after the reaction, stop heating, cooling Suction filtration, get light yellow edaravone crude product; |
| Usage | It is mainly used for the synthesis of pyrazolone antipyretic analgesics such as metamizole, antipyrine and aminopyrine; it is also an intermediate for pyrazolone acid dyes such as the acid media jujube BN, permanent yellow G and color film dyes, pesticides and some other fine chemicals. intermediates for the preparation of pyrazolone dyes and pharmaceuticals used as reagents for the determination of cobalt, copper, iron, nickel, silver and vitamin B12, also used for dye synthesis used for the synthesis of antipyrine, aminopyrine, analgin and other drugs, preparation of acid media jujube red BN, yongguhuang G, leather spray dyes such as red G is mainly used in the production of drugs antipyrine, aminopyrine, the raw materials of the static, also used in dyes and color film dyes, pesticides and organic synthesis industry. 1. Mainly used in the production of pharmaceutical antipyrine, aminopyrine, analgin. Also used in dyes and color film dyes, pesticides and organic synthesis industry. And can be used as a chemical reagent for detecting vitamin B12,CO,Fe,Cu,Ni, etc. reagent for reducing carbohydrate detection by ESI/MALDI-MS method reagent for reducing carbohydrate detection by ESI/MALDI-MS. Environmental protection reagent |
| production method | phenylhydrazine is obtained by reacting ethyl acetoacetate. Phenylhydrazine and ethanol were heated to about 50 ° C., and the addition of ethyl acetoacetate was started and refluxed for 4h after the addition. After a little cold, it was left overnight to precipitate yellow crystals, which were filtered, and the crude product was recrystallized with ethanol to be the finished product. Another method is the reaction of phenylhydrazine with butanone amide. Phenylhydrazine was reacted with butanone amide at about 50 ° C. After the reaction, the reaction was filtered, washed with water, and dried to obtain a finished product. Raw material consumption quota: aniline (98%)560kg/t, liquid ammonia 1100kg/t, hydrochloric acid (30%)1280kg/t, acetic acid 1060kg/t, sulfuric acid (93%)840kg/t, sulfur 850kg/t, ammonium nitrite (95%)440kg/t. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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View History
Raw Materials for 3-methyl-1-phenyl-2-pyrazolin-5-on
Ammonium hydroxide
Aniline
Aniline
p-Toluidine
Formaldehyde
Formaldehyde
Formic acid
Sulfuric acid
Dimethyl sulfate
diketene
Ammonium Bisulfite
Sodium nitrite
Sodium nitrite
Hydrochloric acid
Hydrochloric acid
Ammonia
Aniline
Aniline
p-Toluidine
Formaldehyde
Formaldehyde
Formic acid
Sulfuric acid
Dimethyl sulfate
diketene
Ammonium Bisulfite
Sodium nitrite
Sodium nitrite
Hydrochloric acid
Hydrochloric acid
Ammonia
Downstream Products for 3-methyl-1-phenyl-2-pyrazolin-5-on