Methyl 2-Chloro-4-(1H-pyrazol-1-yl)benzoate: Key FAQs
Methyl 2-Chloro-4-(1H-pyrazol-1-yl)benzoate: Key FAQs
Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate is a halogenated aryl pyrazole ester serving as a versatile synthetic building block for medicinal chemistry and agrochemical research.
- Product Name
- Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate
- SKU
- M700570
- Core Functional Groups
- Ester (methyl benzoate), aryl chloride, N-aryl pyrazole
- Primary Application
- Synthetic intermediate in medicinal chemistry and heterocyclic chemistry
- Supplier
- Aladdin Scientific
What Is Methyl 2-Chloro-4-(1H-pyrazol-1-yl)benzoate?
Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate (SKU M700570) is an organic compound featuring a benzoate methyl ester core substituted at the 2-position with a chloro group and at the 4-position with a 1H-pyrazol-1-yl (N-linked pyrazole) moiety. The combination of an electrophilic aryl chloride and a nucleophilic-capable pyrazole ring within the same molecule makes this compound a multifunctional building block. It belongs to the broader class of N-arylpyrazole derivatives, which are well-represented in drug discovery programs targeting a variety of biological pathways.
Key Chemical Properties and Handling
This compound contains three reactive features relevant to synthetic chemists: (1) the methyl ester, which can be hydrolyzed to the corresponding carboxylic acid or converted to amides and other acyl derivatives; (2) the aryl chloride at the 2-position, which is amenable to transition-metal-catalyzed cross-coupling reactions (e.g., Suzuki, Buchwald-Hartwig) or nucleophilic aromatic substitution under appropriate conditions; and (3) the pyrazole ring, which can participate in further functionalization at the C-3, C-4, or C-5 positions. Handle the compound in a well-ventilated fume hood, using standard personal protective equipment including gloves, safety glasses, and a laboratory coat. Consult the Safety Data Sheet (SDS) before use for specific hazard classifications and first-aid measures.
Storage and Stability Recommendations
As a general best practice for aryl chloride and ester-containing compounds, Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate should be stored in a tightly sealed container away from moisture, heat, and strong nucleophiles or bases that could hydrolyze the ester or displace the chloride. Storage at cool, dry conditions (typically 2–8 °C or as specified on the product label) is recommended to maximize shelf life. Avoid repeated freeze-thaw cycles if the compound is dissolved in solvent. Always verify current storage specifications on the Aladdin Scientific product page or certificate of analysis for lot-specific guidance.
Typical Applications in Research
N-arylpyrazole scaffolds are prevalent in medicinal chemistry as pharmacophores for kinase inhibitors, anti-inflammatory agents, and other bioactive molecules. Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate can serve as: (a) a precursor to carboxylic acid analogs via ester hydrolysis for use in amide-bond coupling; (b) a cross-coupling partner at the aryl chloride position to introduce diverse aryl, heteroaryl, or amino substituents; and (c) a fragment for fragment-based drug discovery (FBDD) programs. It may also find application in agrochemical research, where pyrazole-containing compounds have demonstrated biological activity.
Ordering and Quality Information
Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate is available from Aladdin Scientific under SKU M700570. To place an order, visit the Aladdin Scientific website and search by SKU or product name. A certificate of analysis (COA) including purity data is available upon request or downloadable from the product page. For bulk quantities, custom packaging, or technical inquiries, contact Aladdin Scientific customer service. Ensure that procurement documentation references SKU M700570 to avoid ordering errors.
Frequently asked questions
What is the CAS number for Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate?
The CAS number for Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate is not explicitly provided in the current source material. Please refer to the Aladdin Scientific product page for SKU M700570 or the certificate of analysis for the confirmed CAS registry number.
What solvents are recommended for dissolving Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate?
Based on the compound's structure—a moderately polar aromatic ester with a chloro substituent and a pyrazole ring—common organic solvents such as dimethyl sulfoxide (DMSO), dichloromethane (DCM), ethyl acetate, or tetrahydrofuran (THF) are likely suitable. Aqueous solubility is expected to be low. Specific solubility data should be confirmed on the product COA or by contacting Aladdin Scientific technical support.
Can Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate be used directly in Suzuki cross-coupling reactions?
Yes, aryl chlorides are established electrophilic coupling partners in palladium-catalyzed Suzuki-Miyaura reactions, although they are generally less reactive than aryl bromides or iodides and may require more active catalyst systems (e.g., bulky phosphine ligands or N-heterocyclic carbene ligands). The methyl ester and pyrazole substituents are typically compatible with standard Suzuki conditions. Optimization of catalyst loading, base, and solvent is recommended for best yields.
What purity grade is available for SKU M700570 from Aladdin Scientific?
Specific purity grade information for SKU M700570 is not detailed in the current source material. Please consult the certificate of analysis available on the Aladdin Scientific website or contact customer service for lot-specific purity data.
Is Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate suitable for biological assays directly, or must it be further derivatized?
This compound is primarily positioned as a synthetic building block and intermediate rather than a finished bioactive molecule. For most biological assays, further derivatization—such as ester hydrolysis to the acid, amide formation, or cross-coupling to install pharmacophoric groups—would be required to achieve target-relevant biological activity. Researchers should design analogs based on their specific biological target and structure-activity relationship (SAR) goals.
References
- Aladdin Scientific product page for Methyl 2-chloro-4-(1H-pyrazol-1-yl)benzoate, SKU M700570.
- Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007
- Küenburg, B. et al. N-Arylpyrazole scaffolds in drug discovery: a review. (General reference — specific author, journal, and year not confirmed from source material.)
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