Basic information Safety Supplier Related

4-Methylpyrazole

Basic information Safety Supplier Related

4-Methylpyrazole Basic information

Product Name:
4-Methylpyrazole
Synonyms:
  • 1H-Pyrazole, 4-methyl-
  • 4-Methyl-1H-pyrazole
  • 4-Methylpyrazol
  • 4-methyl-pyrazol
  • Pyrazole, 4-methyl-
  • 4-METHYLPYRRAZOLE
  • 4-METHYLPYRAZOLE
  • AKOS B014452
CAS:
7554-65-6
MF:
C4H6N2
MW:
82.1
EINECS:
231-445-0
Product Categories:
  • Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines
  • Bioactive Small Molecules
  • Building Blocks
  • C3 to C5
  • Cell Biology
  • Chemical Synthesis
  • F
  • Heterocyclic Building Blocks
  • Pyrazoles
Mol File:
7554-65-6.mol
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4-Methylpyrazole Chemical Properties

Melting point:
13°C
Boiling point:
99-100 °C6 mm Hg(lit.)
Density 
0.993 g/mL at 25 °C(lit.)
vapor pressure 
7.136-87.85Pa at 20-50℃
refractive index 
n20/D 1.495(lit.)
Flash point:
205 °F
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
solubility 
soluble
pka
14.95±0.50(Predicted)
form 
Liquid After Melting
color 
Clear colorless to yellow
Specific Gravity
0.993
Water Solubility 
soluble
Sensitive 
Hygroscopic
Merck 
14,4226
BRN 
105204
LogP
1.097 (est)
CAS DataBase Reference
7554-65-6(CAS DataBase Reference)
NIST Chemistry Reference
4-methylpyrazole(7554-65-6)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26-36-24/25
RIDADR 
2810
WGK Germany 
3
RTECS 
UQ7350000
10-23
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29331990
Toxicity
LD50 (7 days) in mice, rats (mmol/kg): 3.8, 3.8 i.v.; 7.8, 6.5 orally (Magnusson)

MSDS

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4-Methylpyrazole Usage And Synthesis

Description

Fomepizole is a competitive inhibitor of alcohol dehydrogenase, the enzyme that catalyzes metabolism of ethylene glycol and methanol to toxic metabolites. At 10 μM in monkeys, it can prevent the formation of toxic alcohol metabolites that generate metabolic acidosis. This compound is typically used as an antidote for ethylene glycol or methanol poisoning.

Description

Fomepizole is the first drug indicated as an antidote for ethylene glycol poisoning (it has also shown promise as a treatment for methanol poisoning). Fomepizole is 4-methyl-1H-pyrazole active as a synthetic alcohol dehydrogenase inhibitor, blocking the formation of toxic ethylene glycol metabolites which are responsible for a severe metabolic acidosis and renal failure. In limited human studies, it reversed the toxicity of potentially lethal doses of ethylene glycol. The main urinary metabolite has been reported to be 4-carboxypyrazole by oxidation of the methyl group. Compared with the current treatment (ethanol), the duration of action is longer and the safety is improved, with no toxic effects reported.

Chemical Properties

clear colourless to yellowish liquid after melting

Originator

Orphan Medical (US)

Uses

Fomepizole (4-Methylpyrazole) can be used as:

  • A reactant to prepare 4-methyl-1-phenyl-1H-pyrazole by reacting with bromobenzene via N-arylation using a copper catalyst.
  • A starting material for the synthesis of 4-methyl-3(5)-nitropyrazole by nitration.
  • A ligand in the preparation of gallium(III) complex of 4-methylpyrazole as potential antitumor and antiviral agent.

Uses

Useful as an antidote in methanol and ethylene glycol poisoning.

Uses

Antidote in methanol or ethylene glycol poisoning;Alcohol dehydrogenase inhibitor

Uses

antidote to ethylene glycol or methanol poisoning

Definition

ChEBI: A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.

Manufacturing Process

Preparation of 4-methylpyrazole
1.0 g (6.67 mmol) of sodium iodide is added to a suspension of 560 g (4.0 mol) of 70% strength sulfuric acid and 62.5 g (1.0 mol) of 80% strength hydrazine hydrate and, at 125°C, 86.4 g (1.2 mol) of isobutyraldehyde are pumped under the surface of the suspension over the course of 2 hours using a metering pump. During and up to 100 min after the addition of isobutyraldehyde, a total of 175 g of water was distilled out, with the temperature of the mixture rising to 135°C. The solution is cooled and adjusted to pH 8.6 with 820 g (5.125 mol) of 25% strength sodium isobutyraldehyde hydroxide solution and is extracted with isobutanol. The combined extracts are concentrated to 82 g in a rotary evaporator and then distilled. The main fraction (boiling point 82°C/7 mbar; 49 g) consists of 82% 4-methylpyrazole. Yield: 49% of theory.

brand name

Antizol (Jazz).

Therapeutic Function

Antidote

General Description

4-Methylpyrazole inhibits CYP2E1 activity. It also acts as alcohol dehydrogenase inhibitor.

Biochem/physiol Actions

Alcohol dehydrogenase inhibitor.

4-MethylpyrazoleSupplier

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