ChemicalBook > CAS DataBase List > 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one

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

Product Name
5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
CAS No.
89-25-8
Chemical Name
5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one
Synonyms
PMP;EDARAVONE;1-Phenyl-3-methyl-5-pyrazolone;5-METHYL-2-PHENYL-2,4-DIHYDRO-3H-PYRAZOL-3-ONE;3-methyl-1-phenyl-1H-pyrazol-5(4H)-one;Norphenazone;3-METHYL-1-PHENYL-5-PYRAZOLONE;3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ONE;MONOPYRAZOLONE;PHENYLMETHYLPYRAZOLON
CBNumber
CB1287462
Molecular Formula
C10H10N2O
Formula Weight
174.2
MOL File
89-25-8.mol
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5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Property

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)
Flash point:
191°C/17mm
storage temp. 
2-8°C
solubility 
3.30g/l
pka
2.73±0.50(Predicted)
form 
Crystalline Powder
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.
InChIKey
QELUYTUMUWHWMC-UHFFFAOYSA-N
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)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
1
RTECS 
UQ9625000
TSCA 
Yes
HS Code 
29331990
Hazardous Substances Data
89-25-8(Hazardous Substances Data)
Toxicity
LD50 orl-rat: 3500 mg/kg LONZA# 08FEB79
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR2348
Product name
Antipyrine Related Compound A
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
50MG
Price
$534
Updated
2024/03/01
Sigma-Aldrich
Product number
443300
Product name
MCI-186
Packaging
500mg
Price
$96.7
Updated
2024/03/01
Sigma-Aldrich
Product number
1040016
Product name
Antipyrine Related Compound A
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
25mg
Price
$1300
Updated
2024/03/01
TCI Chemical
Product number
M0687
Product name
3-Methyl-1-phenyl-5-pyrazolone
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$21
Updated
2024/03/01
TCI Chemical
Product number
M0687
Product name
3-Methyl-1-phenyl-5-pyrazolone
Purity
>98.0%(HPLC)(T)
Packaging
500g
Price
$43
Updated
2024/03/01
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5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Chemical Properties,Usage,Production

Description

Edaravone was marketed in Japan for improving neurologic recovery following acute brain infarction. Currently, several agents classified as neuroprotectants and acting by diverse mechanisms (inhibition of glutamate release, blockade of calcium channels, lazaroids) have been marketed for treating the outcomes of brain damage due to trauma, ischemia or cardiac arrest. Edavarone is the first antioxidant with free radical scavenging activity to be introduced for this pathology. This previously described molecule (in particular as norantipyrine, one of three metabolites of antipyrine in mammals) can be simply prepared by direct cyclization of phenylhydrazine with alkylacetoacetate. Edarevone is a lipophilic agent, readily accessible to brain tissue, that is capable of reducing edema in the brain following ischemia by blocking the arachidonic acid cascade triggering peroxidative neurodegeneration. Interestingly, this agent has been shown to quench active oxygen species in endothelial cell homogenate, as well as inhibiting in vitro lipid peroxidative disintegration of membranes, so making this compound effective during reperfusion 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) Watanabe et al. (1994), Protective effects of MCI-186 on cerebral ischemia:possible involvement of free radical scavenging and antioxidant actions; J. Pharmacol. Exp. Ther., 268 1597 2) Yoshida et al. (2006) Neuroprotective effects of edaravone:a novel free radical scavenger in cerebrovascular injury; CNS Drug Reviews, 12 9 3) Kawasaki et al. (2007) 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. Pharmacol. Exp. Ther., 322 274

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

Raw materials

Acetyl ketene AMMONIUM NITRITE, 20% SOLN Acetoacetamide Ammonium hydroxide Ethanol Acetoxyacetic acid Ammonium bisulfite Formaldehyde Formic acid Sodium nitrite Aniline Hydrochloric acid p-Toluidine METHANE Sulfuric acid Sodium carbonate Ammonia Sodium metabisulfite Dimethyl sulfate

Preparation Products

ACID YELLOW 17 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 Tracid Light Yellow G DIFENZOQUAT METHYLSULFATE Mordant Red 7 Pyrazole 3,5-DIPHENYLPYRAZOLE
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View Lastest Price from 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Edaravone 89-25-8
Price
US $180.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-06-06
WUHAN FORTUNA CHEMICAL CO., LTD
Product
5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one 89-25-8
Price
US $0.00/Kg/Drum
Min. Order
100g
Purity
99%min
Supply Ability
10KGS
Release date
2021-07-17
HebeiShuoshengImportandExportco.,Ltd
Product
5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one 89-25-8
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-05

89-25-8, 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-oneRelated Search:

PHENYL VALERATE Kresoxim-methyl Methanol Methyl acrylate Basic Violet 1 Cefazolin sodium salt Methyl acetate Acetonitrile Cefazolin Edaravone N-Oxide Paraquat dichloride Methylparaben Dihydromyrcenol Edaravone Glucuronide 1,2-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one 4,5-dihydro-a-(hydroxyMethyl)-a,3-diMethyl-5-oxo-1-phenyl-1H-Pyrazole-4-Methanesulfonic acid BISPYRAZOLONE Edaravone Impurity 26

  • 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
  • 3-Methyl-1-phenylpyrazol-5-one
  • 3-Methyl-1-phenylpyrazolin-5-one
  • 5-Pyrazolone, 3-methyl-1-phenyl-
  • Developer Z
  • 3-Methyl-1-pehnyl-2-pyrazolin-5-one
  • 1-phenyl-3-methyl-5-pyrazolone(PMP)
  • Adaravone
  • 3-Methyl-1-phenyl-2-pyrazolin-5-one, 98+%
  • 1-Phenyl-3-methyl-1H-4,5-dihydropyrazol-5-one
  • Radicu
  • 3-Methyl-1-phenyl-5-pyrazolido
  • 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-
  • N-demethylantipyrine
  • PHENYLMETHYLPYRAZOLON
  • 3-methyl-1-pheny-1-1H-pyrazol-5(4H)-one
  • 3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ONE [NORANTIPYRINE]
  • Radicut
  • Methyl-1-phenyl-2-pyrazolin-5-one, 3-
  • 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
  • 1-Phenyl-3-methyl-2-prazolin-5-one
  • 3-Methyl-1-phenylpyrazolin-5(4H)-one
  • 5-Methyl-2-phenyl-1H-pyrazol-3-one
  • -1,2-dihydropyrazoL
  • MCI-186
  • EDARAVONE
  • C.I. Developer 1
  • AURORA KA-3365
  • 2,4-dihydro-5-methyl-2-phenyl-3h-pyrazol-3-one
  • 1-PHENYL-3-METHYL-5-OXO-2-PYRAZOLINE
  • 1-PHENYL-3-METHYL-5-PYRAZALONE
  • 5-METHYL-2-PHENYL-2,4-DIHYDRO-3H-PYRAZOL-3-ONE
  • 5-METHYL-2-PHENYL-2,4-DIHYDRO-PYRAZOL-3-ONE
  • 3-METHYL-1-PHENYL-5-PYRAZOLONE
  • 3-METHYL-1-PHENYL-5-PYROZOLENE
  • 3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ONE
  • 3-METHYL-1-PHENYL-2-PYRAZOLINE-5-ONE
  • AKOS B029819
  • developerz
  • Methylphenylpyrazolone
  • NCI-C03952
  • norantipyrine
  • Norphenazone
  • NSC-12
  • NSC-26139
  • NSC-2629
  • phenylmethylpyrazolone
  • 1-Fenyl-3-methyl-2-pyrazolin-5-on
  • 1-Phenyl-3-methyl-5-pyrazolon
  • 1-Phenyl-3-methylpyrazolone
  • 1-Phenyl-3-methylpyrazolone-5