(3-Methyl-1H-pyrazol-4-yl)methanol: Properties & Lab Use Guide

(3-Methyl-1H-pyrazol-4-yl)methanol is a pyrazole-derived primary alcohol widely employed as a versatile building block and synthetic intermediate in medicinal chemistry and heterocyclic compound research.

Product Name

(3-Methyl-1H-pyrazol-4-yl)methanol

SKU

M729873

Core Scaffold

3-Methylpyrazole with a hydroxymethyl substituent at C-4

Functional Groups

Primary alcohol (–CH₂OH) and pyrazole NH

Primary Use

Synthetic building block for drug discovery and heterocyclic chemistry

Supplier

Aladdin Scientific

Chemical Identity and Structure

(3-Methyl-1H-pyrazol-4-yl)methanol consists of a five-membered pyrazole ring bearing a methyl group at the 3-position and a primary hydroxymethyl group (–CH₂OH) at the 4-position, with an NH tautomeric site at N-1. The coexistence of the hydrogen-bond-donating NH and OH groups alongside the basic pyrazole nitrogen atoms makes this compound highly functionalized relative to its molecular weight. These features facilitate diverse downstream transformations including oxidation of the alcohol to the corresponding aldehyde or carboxylic acid, O-alkylation, O-acylation, and N-alkylation at the ring nitrogen, making it a valuable entry point into pyrazole-containing libraries.

Research Applications

(3-Methyl-1H-pyrazol-4-yl)methanol serves as a key building block in medicinal chemistry programs targeting enzyme inhibition, receptor modulation, and agrochemical discovery. The pyrazole scaffold is a privileged heterocyclic motif found in numerous approved pharmaceuticals and crop-protection agents. The hydroxymethyl handle at C-4 provides a convenient handle for linker attachment in fragment-based drug design, prodrug synthesis, and the preparation of fluorescent probes or PET tracers when labeled appropriately. Researchers also use this compound as a precursor to pyrazole-4-carboxaldehyde via Swern or Dess–Martin oxidation, which can then be elaborated through reductive amination or Wittig chemistry.

In materials science, pyrazolyl methanol derivatives have been explored as ligands for coordination polymers and metal-organic frameworks (MOFs) where the dual donor sites (N and O) support diverse coordination modes.

Handling, Storage, and Safety Guidelines

Personal Protective Equipment: Handle (3-Methyl-1H-pyrazol-4-yl)methanol wearing appropriate nitrile gloves, safety glasses, and a laboratory coat. Work in a well-ventilated area or fume hood to minimise inhalation exposure to dust or vapour.

Storage: Store the compound in a tightly sealed container in a cool, dry location away from strong oxidising agents, strong acids, and incompatible materials. Refrigerated storage (2–8 °C) is recommended for long-term preservation of purity. Protect from prolonged exposure to light and moisture.

Spill and Waste Disposal: In the event of a spill, contain the material and collect it using appropriate absorbent material. Dispose of chemical waste in accordance with local, national, and institutional regulations. Do not pour down drains.

First Aid: In case of skin or eye contact, rinse immediately with copious amounts of water. If ingested or inhaled, seek medical attention promptly. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for complete hazard information before use.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies (3-Methyl-1H-pyrazol-4-yl)methanol under SKU M729873. Each lot is characterised to ensure conformance to specification; researchers are encouraged to request the Certificate of Analysis (CoA) for the specific lot number received, which documents purity by HPLC or NMR, along with physical characterisation data. For bulk or custom quantities, contact Aladdin Scientific's sales team for quotation and lead-time information. This compound is intended for research use only and is not approved for pharmaceutical, veterinary, food, or household use.

Frequently asked questions

What are the main synthetic applications of (3-Methyl-1H-pyrazol-4-yl)methanol?

(3-Methyl-1H-pyrazol-4-yl)methanol is primarily used as a heterocyclic building block in medicinal chemistry, enabling access to pyrazole-containing drug candidates through O-alkylation, O-acylation, oxidation to the aldehyde, and N-functionalization. It is also used as a ligand precursor in coordination chemistry and MOF synthesis.

How should (3-Methyl-1H-pyrazol-4-yl)methanol be stored to maintain purity?

The compound should be stored in a tightly sealed container at 2–8 °C, away from moisture, light, strong oxidants, and strong acids. Under these conditions, the compound retains its purity over extended periods. Always check the Certificate of Analysis for lot-specific recommendations.

Is (3-Methyl-1H-pyrazol-4-yl)methanol available in bulk quantities from Aladdin Scientific?

Yes, Aladdin Scientific can accommodate bulk and custom quantity requests for M729873. Researchers and procurement teams should contact the Aladdin Scientific sales department directly to discuss availability, pricing, and lead times for larger orders.

What tautomeric forms does (3-Methyl-1H-pyrazol-4-yl)methanol exist in?

Pyrazoles bearing an NH group can exist as two NH tautomers depending on which ring nitrogen bears the proton. For (3-Methyl-1H-pyrazol-4-yl)methanol, the tautomers differ in methyl and hydroxymethyl positional assignments (3-methyl-4-hydroxymethyl vs. 5-methyl-4-hydroxymethyl pyrazole). The predominant tautomer in solution depends on solvent and concentration; researchers should characterise the tautomeric state relevant to their specific application.

References

1. Elguero, J. Pyrazoles. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R. et al., Eds.; Elsevier: Oxford, 1996; Vol. 3, pp 1–75.
2. Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles. Chem. Rev. 2011, 111, 6984–7034. doi:10.1021/cr100253h
3. Mykhailiuk, P. K. Saturated bioisosteres of benzene: where to go next? Org. Biomol. Chem. 2019, 17, 2839–2849. doi:10.1039/C8OB02183B

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.