5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one CAS 89-25-8

Introduction：Basic information about 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one CAS 89-25-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Basic information

• Product Name: 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
• Synonyms: TIMTEC-BB SBB003801;PMP;MONOPYRAZOLONE;2,4-dihydro-5-methyl-2-phenyl-3h-pyrazol-3-on;2-Pyrazolin-5-one, 3-methyl-1-phenyl-;3H-Pyrazol-3-one,2,4-dihydro-5-methyl-;3-methyl-1-phenyl-2-pyrazolin-5-on;3-methyl-1-phenyl-5-pyrazolon
• CAS: 89-25-8
• MF: C10H10N2O
• MW: 174.2
• EINECS: 201-891-0
• Product Categories: heteroXlink;Cardiovascular APIs;Aromatices;Heterocycles;Intermediates & Fine Chemicals;Pharmaceutical intermediates;API;Aromatics Compounds;Pharmaceuticals;OthersDerivatization Reagents;Coupling;ChromophoresPeptide Synthesis;Glycan Labeling;Glycan Labeling and Analysis;Intermediates of Dyes and Pigments;Derivatization Reagents HPLC;OthersSynthetic Reagents;Peptide Synthesis;UV-VIS;89-25-8
• Mol File: 89-25-8.mol

5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Chemical Properties

• Melting point: 126-128 °C(lit.)
• Boiling point: 287 °C265 mm Hg(lit.)
• density: 1,12 g/cm³
• vapor pressure: 0.016Pa at 20℃
• refractive index: 1.6300 (estimate)
• Fp: 191°C/17mm
• storage temp.: 2-8°C
• solubility: 3.30g/l
• form: Crystalline Powder
• pka: 2.73±0.50(Predicted)
• color: Yellow to beige
• PH: 4.0-4.4 (H2O, 20℃)(saturated aqueous solution)
• Water Solubility: 3 g/L (20 ºC)
• Merck: 14,6713
• BRN: 609575
• 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.
• Major Application: peptide synthesis
• Cosmetics Ingredients Functions: HAIR DYEING
• InChI: 1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3
• InChIKey: QELUYTUMUWHWMC-UHFFFAOYSA-N
• SMILES: CC1=NN(C(=O)C1)c2ccccc2
• LogP: 0.75 at 24℃
• CAS DataBase Reference: 89-25-8(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-(89-25-8)
• EPA Substance Registry System: 1-Phenyl-3-methyl-5-pyrazolone (89-25-8)

Safety Information

• Hazard Codes: Xi
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 1
• RTECS: UQ9625000
• TSCA: TSCA listed
• HS Code: 29331990
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Acute Tox. 4 Oral Eye Irrit. 2
• Hazardous Substances Data: 89-25-8(Hazardous Substances Data)
• Toxicity: LD50 orl-rat: 3500 mg/kg LONZA# 08FEB79

5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Usage And Synthesis

Description

Edaravone was marketed in Japan for improving neurologic recoveryfollowing acute brain infarction. Currently, several agents classified as neuroprotectantsand acting by diverse mechanisms (inhibition of glutamate release, blockade of calciumchannels, lazaroids) have been marketed for treating the outcomes of brain damage due totrauma, ischemia or cardiac arrest. Edavarone is the first antioxidant with free radicalscavenging activity to be introduced for this pathology. This previously described molecule(in particular as norantipyrine, one of three metabolites of antipyrine in mammals) can besimply prepared by direct cyclization of phenylhydrazine with alkylacetoacetate. Edarevoneis a lipophilic agent, readily accessible to brain tissue, that is capable of reducing edemain the brain following ischemia by blocking the arachidonic acid cascade triggeringperoxidative neurodegeneration. Interestingly, this agent has been shown to quench activeoxygen species in endothelial cell homogenate, as well as inhibiting in vitro lipid peroxidative disintegration of membranes, so making this compound effective duringreperfusion following ischemic injury. As an additional indication, phase III trials started with edaravone for increasing the chance of recovery after subarachnoid hemorrhage.

Description

MCI-186 is a free radical scavenger with diverse protective effects in vivo. Most notably, it reduces damage due to ischemia-reperfusion injury in lung, liver, and brain in animal models of transplant, infection, traumatic brain injury, and stroke. MCI-186 provides these protective effects, at least in part, by reducing reactive oxygen species, inhibiting apoptosis, and blocking nonenzymatic peroxidation and lipoxygenase activity.

Chemical Properties

Off white to light yellow powder

Originator

Mitsubishi Pharma (Japan)

Uses

3-Methyl-1-phenyl-2-pyrazolin-5-one used as reagent for detection of reducing carbohydrates by ESI/MALDI -MS.

Uses

antioxidant, lipoxygenase inhibitor

Uses

Edaravone inhibits the disease activity in rheumatoid arthritis.

Definition

ChEBI: A pyrazolone that is 2,4-dihydro-3H-pyrazol-3-one which is substituted at positions 2 and 5 by phenyl and methyl groups, respectively.

Brand name

Radicut

General Description

A free radical scavenger and antioxidant that reduces post-ischemic brain injury. Inhibits iron-dependent peroxidation in rat brain homogenates (IC₅₀ = 15 μM). Inhibits mitochondrial permeability transition pore.

Hazard

Toxic by ingestion.

Flammability and Explosibility

Not classified

Biological Activity

A radical scavenger and antioxidant which is able to protect against the effects of ischemia, probably by inhibiting the lipoxygenase system. Protects against MPTP-induced neurotoxicity.

Biochem/physiol Actions

Product does not compete with ATP.

Safety Profile

Moderately toxic by ingestion andintraperitoneal routes. An eye irritant. When heated todecomposition it emits toxic fumes of NOx.

storage

Store at RT

Purification Methods

Crystallise the pyrazolone from hot H2O, EtOH or EtOH/water (1:1). It complexes with metals. [Veibel et al. Acta Chim Scand 6 1066 1952, Beilstein 24 II 9, 24 III/IV 71.]

References

[1] T WATANABE. Protective effects of MCI-186 on cerebral ischemia: possible involvement of free radical scavenging and antioxidant actions.[J]. Journal of Pharmacology and Experimental Therapeutics, 1994, 268 3: 1597-1604.
[2] HIROSHI YOSHIDA. Neuroprotective Effects of Edaravone: a Novel Free Radical Scavenger in Cerebrovascular Injury[J]. CNS drug reviews, 2006, 12 1: 9-20. DOI:10.1111/j.1527-3458.2006.00009.x
[3] TOSHIYUKI KAWASAKI. Edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one), a radical scavenger, prevents 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurotoxicity in the substantia nigra but not the striatum.[J]. Journal of Pharmacology and Experimental Therapeutics, 2007, 322 1: 274-281. DOI:10.1124/jpet.106.119206

5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Preparation Products And Raw materials

• Raw materials: Ethanol-->Hydrochloric acid-->Sulfuric acid-->Sodium carbonate-->Sodium nitrite-->Ammonium hydroxide-->Ammonia-->Formaldehyde-->Dimethyl sulfate-->Aniline-->Formic acid-->Sodium metabisulfite-->Acetyl ketene-->p-Toluidine-->METHANE-->Acetoxyacetic acid-->Ammonium bisulfite-->Acetoacetamide-->AMMONIUM NITRITE, 20% SOLN
• Preparation Products: Pyrazole-->DIFENZOQUAT METHYLSULFATE-->Tracid Light Yellow G-->3,5-DIPHENYLPYRAZOLE-->ACID YELLOW 17-->Mordant Red 7-->sodium [2,4-dihydro-4-[(2-hydroxy-5-nitrophenyl)azo]-5-methyl-2-phenyl-3H-pyrazol-3-onato(2-)][1-[(2-hydroxy-4-nitrophenyl)azo]-2-naphtholato(2-)]cobaltate(1-)-->Neutral Bordeaux D-BN-->Cuprate(2-), [4-[bis[4-(diethylamino)phenyl]hydroxymethyl]-5-[(4,5-dihydro-3-methyl-5-(oxo-κO)-1-phenyl-1H-pyrazol-4-yl)azo-κN1]-6-(hydroxy-κO)-1,3-benzenedisulfonato(4-)]-, disodium