Production Method 1

27258-32-8

84547-62-6

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  0 °C; overnight, rt

Reference

An Approach to 1,1-Disubstituted Pyrazolylcyclopropane Building Blocks

Nosik, Pavel S.; et al, SynOpen, 2017, 1(1), 0084-0090

Production Method 2

84547-60-4

84547-62-6

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride

Reference

1,3- And 1,5-dimethylpyrazole-based syntheses. VI. Stilbene and 1,4-distyrylbenzene analogs containing 3-, 4-, and 5-pyrazolyl radicals

Perevalov, V. P.; et al, Zhurnal Obshchei Khimii, 1982, 52(11), 2598-605

Production Method 3

930-36-9

84547-62-6

84547-61-5

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane
1.2 -
1.3 Solvents: Water
1.4 Reagents: Sodium borohydride Solvents: Diethyl ether ,  Methanol
1.5 Reagents: Hydrochloric acid Solvents: Water

Reference

Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems. Part IV. 2-Alkyl substituents containing cationic heteroaromatics linked via a C-C bond

Azami, H.; et al, Bioorganic & Medicinal Chemistry, 2001, 9(4), 961-982

Production Method 4

25016-20-0

84547-62-6

Reaction Conditions

1.1 Reagents: Thionyl chloride
2.1 Reagents: Lithium aluminum hydride

Reference

1,3- And 1,5-dimethylpyrazole-based syntheses. VI. Stilbene and 1,4-distyrylbenzene analogs containing 3-, 4-, and 5-pyrazolyl radicals

Perevalov, V. P.; et al, Zhurnal Obshchei Khimii, 1982, 52(11), 2598-605

(1-Methyl-1H-pyrazol-3-yl)methanol Raw materials

• 1-Methyl-1H-pyrazole-3-carbaldehyde
• 1-methyl-1H-pyrazole
• 1-methyl-1H-pyrazole-3-carbonyl chloride
• 1-Methyl-1H-pyrazole-3-carboxylic acid

(1-Methyl-1H-pyrazol-3-yl)methanol Preparation Products

• (1-Methyl-1H-pyrazol-3-yl)methanol (84547-62-6)
• (1-Methyl-1H-pyrazol-5-yl)methanol (84547-61-5)

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Professional Introduction to (1-Methyl-1H-pyrazol-3-yl)methanol (CAS No. 84547-62-6)

(1-Methyl-1H-pyrazol-3-yl)methanol, identified by its Chemical Abstracts Service (CAS) number 84547-62-6, is a significant compound in the realm of pharmaceutical chemistry and bioorganic synthesis. This heterocyclic alcohol has garnered attention due to its versatile structural framework, which makes it a valuable intermediate in the development of various pharmacologically active molecules. The compound belongs to the pyrazole class, a scaffold that is widely recognized for its presence in numerous bioactive natural products and synthetic drugs.

The structural motif of (1-Methyl-1H-pyrazol-3-yl)methanol consists of a six-membered aromatic ring system containing two nitrogen atoms, with a methyl group at the 1-position and a hydroxymethyl group at the 3-position. This particular configuration imparts unique electronic and steric properties, making it an attractive building block for medicinal chemists. The presence of the hydroxymethyl group (-CH?OH) not only facilitates further functionalization but also suggests potential applications in the synthesis of more complex molecules, such as protease inhibitors, kinase inhibitors, and other therapeutic agents.

In recent years, there has been a surge in research focused on developing novel heterocyclic compounds with potential therapeutic applications. Pyrazole derivatives, in particular, have been extensively studied due to their broad spectrum of biological activities. For instance, several pyrazole-based compounds have shown promise as antiviral, antibacterial, anti-inflammatory, and anticancer agents. The compound (1-Methyl-1H-pyrazol-3-yl)methanol is no exception and has been explored in various preclinical studies as a precursor for more sophisticated drug candidates.

One of the most compelling aspects of (1-Methyl-1H-pyrazol-3-yl)methanol is its role as a key intermediate in the synthesis of more complex pharmacophores. Researchers have leveraged its structural features to develop novel analogs with enhanced binding affinity and selectivity towards specific biological targets. For example, modifications at the 5-position of the pyrazole ring have been shown to modulate the pharmacokinetic properties of derived compounds, improving their oral bioavailability and metabolic stability. Such findings underscore the importance of this compound in drug discovery pipelines.

The synthesis of (1-Methyl-1H-pyrazol-3-yl)methanol typically involves multi-step organic transformations, often starting from commercially available pyrazole derivatives. One common approach involves the alkylation of 3-hydroxypyrazole with methyl halides or sulfonates, followed by reduction to introduce the hydroxymethyl group. Advances in catalytic methods have also enabled more efficient and sustainable synthetic routes, reducing the environmental impact of large-scale production.

The chemical reactivity of (1-Methyl-1H-pyrazol-3-yl)methanol allows for further derivatization into various functional groups, including esters, amides, and ureas. These derivatives can then be explored for their biological activity against a range of diseases. For instance, recent studies have demonstrated that pyrazole-based esters exhibit potent inhibitory effects on certain enzymes implicated in cancer progression. The hydroxymethyl group serves as a versatile handle for these modifications, enabling rapid diversification of the molecular library.

In addition to its pharmaceutical applications, (1-Methyl-1H-pyrazol-3-yl)methanol has found utility in materials science and agrochemical research. Its ability to act as a ligand in coordination chemistry has led to the development of novel metal complexes with potential catalytic properties. Furthermore, its incorporation into agrochemical formulations has shown promise in enhancing the efficacy of pesticides and herbicides while reducing environmental toxicity.

The growing interest in green chemistry has also influenced the synthesis methodologies for compounds like (1-Methyl-1H-pyrazol-3-yl)methanol. Researchers are increasingly employing solvent-free reactions, microwave-assisted synthesis, and biocatalytic approaches to improve yield and reduce waste. These innovations not only make production more cost-effective but also align with global sustainability goals.

Looking ahead, the future prospects for (1-Methyl-1H-pyrazol-3-yl)methanol appear promising as new research continues to uncover its potential applications. The integration of computational chemistry and artificial intelligence into drug discovery is expected to accelerate the identification of novel derivatives with enhanced therapeutic profiles. Furthermore, collaborations between academia and industry are likely to drive innovation in both synthetic methodologies and biological evaluations.

In conclusion, (1-Methyl-1H-pyrazol-3-yl)methanol (CAS No. 84547-62-6) represents a cornerstone compound in modern medicinal chemistry. Its unique structural features and versatile reactivity make it an indispensable tool for researchers developing new therapeutic agents across multiple disease areas. As advancements continue to emerge in synthetic chemistry and computational biology, this compound is poised to play an even greater role in shaping the future of pharmaceutical innovation.

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