7554-65-6 Usage
Description
4-Methylpyrazole, also known as Fomepizole, is a synthetic compound belonging to the class of pyrazoles. It is a clear, colorless to yellowish liquid after melting and is characterized by its ability to inhibit CYP2E1 activity. Fomepizole acts as a competitive alcohol dehydrogenase inhibitor, blocking the formation of toxic metabolites from methanol and ethylene glycol poisoning.
Uses
Used in Antidote Applications:
4-Methylpyrazole is used as an antidote for methanol and ethylene glycol poisoning. It functions as an alcohol dehydrogenase inhibitor, preventing the formation of toxic metabolites responsible for severe metabolic acidosis and renal failure. In limited human studies, it has been shown to reverse the toxicity of potentially lethal doses of ethylene glycol.
Used in Pharmaceutical Industry:
4-Methylpyrazole is used as a reactant to prepare 4-methyl-1-phenyl-1H-pyrazole by reacting with bromobenzene via N-arylation using a copper catalyst. It is also used as a starting material for the synthesis of 4-methyl-3(5)-nitropyrazole by nitration.
Used in Chemical Research:
4-Methylpyrazole serves as a ligand in the preparation of gallium(III) complex of 4-methylpyrazole, which has potential applications as an antitumor and antiviral agent.
Brand Name:
The brand name for 4-Methylpyrazole is Antizol, which is marketed by Jazz Pharmaceuticals.
Originator
Orphan Medical (US)
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.
Biochem/physiol Actions
Alcohol dehydrogenase inhibitor.
Check Digit Verification of cas no
The CAS Registry Mumber 7554-65-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,5,5 and 4 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 7554-65:
(6*7)+(5*5)+(4*5)+(3*4)+(2*6)+(1*5)=116
116 % 10 = 6
So 7554-65-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H6N2/c1-4-2-5-6-3-4/h2-3H,1H3,(H,5,6)
7554-65-6Relevant articles and documents
4-methylpyrazole preparation method
-
Paragraph 0018; 0019; 0020, (2017/07/22)
The invention discloses a 4-methylpyrazole preparation method. According to the preparation method, 3-amino-2-methylacrolein and formamide are utilized as main raw materials, methylbenzene is utilized as solvent, 4-methylpyrazole is prepared through normal-pressure reaction, and a 4-methylpyrazole finished product can be prepared by rectifying a crude product. The preparation method is simple, has moderate reaction conditions and avoids high-pressure reaction; the main raw materials are safe and environment-friendly; the product has high purity and is more favorable for industrial production.
ULTRAPURE 4-METHYLPYRAZOLE
-
Page/Page column 8-9, (2008/06/13)
Disclosed is an ultrapure 4-methylpyrazole containing less than 0.1% pyrazole and containing less than 10 ppm each of hydrazine and nitrobenzaldehyde. The ultrapure 4-methylpyrazole is prepared by a novel process so that less than 0.01% of ethylvinyl ether is present.
Preparation of pyrazole and its derivatives
-
, (2008/06/13)
A process for preparing pyrazole and its derivatives of the formula I STR1 where R1, R2, R3 and R4 are each hydrogen, halogen, nitro, carboxyl, sulfonyl or C-organic radicals, from alpha,beta-unsaturated carbonyl compounds of the formula II STR2 and hydrazine or hydrazine derivatives of the formula III wherein, initially without additional diluent, an alpha,beta-unsaturated carbonyl compound of the formula II is reacted with hydrazine or a hydrazine derivative of the formula III, and the resulting reaction mixture is reacted in another step with a mixture of sulfuric acid and iodine or a compound which liberates iodine or hydrogen iodide.