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Comprehensive Guide to 1-(4-Methylbenzenesulfonyl)piperidine-3-carbohydrazide (CAS 312286-45-6): Properties, Applications & Market Insights

1-(4-Methylbenzenesulfonyl)piperidine-3-carbohydrazide (CAS 312286-45-6) is a specialized sulfonamide-derived carbohydrazide compound gaining attention in pharmaceutical and chemical research. This white to off-white crystalline powder with a molecular formula of C₁₃H₁₉N₃O₃S exhibits unique structural features combining a piperidine ring, tosyl group, and carbohydrazide moiety, making it valuable for various synthetic applications.

The compound's molecular weight of 297.37 g/mol and moderate polarity (logP ≈ 1.2) contribute to its solubility profile—soluble in polar organic solvents like DMSO and methanol, while sparingly soluble in water. Researchers particularly value its hydrazide functional group which serves as a versatile building block for constructing heterocyclic compounds. Recent studies highlight its potential as a precursor for antimicrobial agents and enzyme inhibitors, aligning with current trends in antibiotic resistance research and targeted drug design.

In synthetic chemistry, 1-(4-Methylbenzenesulfonyl)piperidine-3-carbohydrazide demonstrates remarkable utility for: Schiff base formation (reacting with aldehydes/ketones), heterocycle construction (pyrazole, triazole synthesis), and as a protecting group strategy in multi-step syntheses. Its tosyl-protected piperidine structure offers steric control in asymmetric reactions, while the hydrazide moiety enables click chemistry applications—a hot topic in bioconjugation and material science.

The pharmaceutical industry explores derivatives of this compound for neurological targets (GABA receptor modulation) and metabolic enzymes (carbonyl reductase inhibition), responding to growing demand for CNS therapeutics and anti-diabetic agents. Analytical characterization typically involves HPLC purity analysis (≥95%), FT-IR spectroscopy (characteristic N-H stretch at 3250 cm^-1), and mass spectrometry (ESI+ m/z 298.1 [M+H]⁺).

Market analysis shows increasing procurement of CAS 312286-45-6 by contract research organizations (CROs) and academic labs, particularly for fragment-based drug discovery projects. The compound's price ranges $80-$120/g at research quantities, with lead times of 2-4 weeks from specialty suppliers. Proper storage requires protection from moisture (desiccated at 2-8°C), addressing stability concerns common with hydrazide compounds.

Emerging applications include its use as a linker in PROTAC technology (targeted protein degradation) and as a scaffold for covalent inhibitors—key areas in cancer research. The compound's structure-activity relationship (SAR) studies benefit from its three modifiable regions: sulfonyl group, piperidine nitrogen, and hydrazide terminus. Recent patent literature (2022-2023) describes analogs with improved blood-brain barrier permeability, addressing a major challenge in neuropharmacology.

Quality control protocols for 1-(4-Methylbenzenesulfonyl)piperidine-3-carbohydrazide emphasize residual solvent analysis (GC-MS) and heavy metal screening (ICP-MS), especially for GMP-grade material. The compound's synthetic route typically involves piperidine-3-carboxylic acid protection, tosylation, and hydrazide formation—processes optimized for minimal byproduct generation. Researchers should note its incompatibility with strong oxidizers and acidic conditions that may cleave the sulfonamide bond.

With the growing emphasis on sustainable chemistry, recent methodological improvements focus on catalytic tosylation and aqueous workup procedures to reduce environmental impact. The compound's chiral purity (when applicable) is verified by chiral HPLC, important for stereoselective synthesis applications. As a research chemical, it's primarily supplied in 1g to 100g quantities with comprehensive analytical certificates.

Future research directions may explore its potential in biomaterials functionalization and diagnostic probe development, capitalizing on the reactive hydrazide group. The compound's balanced lipophilicity profile makes it particularly interesting for medicinal chemistry optimization projects addressing drug delivery challenges. Current literature suggests its derivatives may show activity against protein-protein interactions—a frontier in therapeutic development.

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