[(2-Chlorophenyl)methyl]hydrazine Dihydrochloride: Lab Handling Guide

[(2-chlorophenyl)methyl]hydrazine dihydrochloride is a reactive hydrazine derivative used as a key synthetic intermediate in the preparation of heterocyclic compounds, pharmacophore scaffolds, and specialty organic molecules in research and medicinal chemistry laboratories.

Product Name

[(2-chlorophenyl)methyl]hydrazine dihydrochloride

SKU

C177042

Chemical Class

Arylbenzyl hydrazine salt (dihydrochloride form)

Primary Application

Intermediate in heterocyclic and medicinal chemistry synthesis

Physical Form

Solid salt (dihydrochloride)

Storage Recommendation

Store in a cool, dry, well-ventilated area, away from moisture and incompatible materials

Chemical Identity and Properties

[(2-chlorophenyl)methyl]hydrazine dihydrochloride (Aladdin SKU: C177042) is an aryl-substituted benzylhydrazine presented in its stable dihydrochloride salt form. The parent free base contains a hydrazine functional group (–NH–NH₂) tethered to a 2-chlorobenzyl moiety. Converting the free base to the dihydrochloride salt significantly improves the compound's stability, shelf life, and ease of handling relative to free hydrazines, which are generally more sensitive to oxidation and moisture.

The 2-chloro substitution on the phenyl ring confers distinct electronic and steric properties compared to unsubstituted benzylhydrazine derivatives, making this compound a versatile building block for the synthesis of regiospecific heterocyclic targets. Researchers should consult the product's Certificate of Analysis (CoA) for lot-specific data including purity, melting point, and spectral characterization (NMR, HPLC).

Safe Handling and Storage

Personal Protective Equipment (PPE): Always wear appropriate PPE when handling [(2-chlorophenyl)methyl]hydrazine dihydrochloride. This includes chemically resistant gloves (nitrile or neoprene), a laboratory coat, and safety goggles or a face shield. Because hydrazine-class compounds may pose sensitization risks, handling in a fume hood is strongly recommended to minimize inhalation exposure to dust or aerosols.

Storage: Store the compound in a tightly sealed container in a cool (typically 2–8 °C or as specified on the product label), dry, and well-ventilated location. Keep away from strong oxidizing agents, strong acids beyond necessary handling conditions, and sources of ignition. Segregate from incompatible materials. Monitor the storage container for integrity and label clarity.

Disposal: Dispose of this material and its containers in accordance with local, regional, and national regulations governing hazardous chemical waste. Do not pour down the drain without verifying regulatory compliance. Consult the Safety Data Sheet (SDS) for complete hazard and disposal information before use.

Note: Users must obtain and review the current SDS for C177042 prior to handling. Specific GHS hazard classifications, first-aid measures, and regulatory information are detailed therein.

Applications in Organic and Medicinal Chemistry

[(2-chlorophenyl)methyl]hydrazine dihydrochloride serves as a nucleophilic building block exploited in condensation reactions to form hydrazones, pyrazoles, pyrazolines, triazoles, and other nitrogen-containing heterocycles. These scaffolds are of high relevance in medicinal chemistry programs targeting anti-inflammatory, antifungal, antitumor, and antimicrobial activities, though users should validate specific biological outcomes in their own experimental systems.

Key reaction types include:

• Knorr-type pyrazole synthesis: Condensation with 1,3-dicarbonyl compounds yields substituted pyrazoles, a privileged scaffold in drug discovery.
• Hydrazone formation: Reaction with aldehydes or ketones produces hydrazones useful as ligands, probes, or further synthetic intermediates.
• Fischer indole synthesis: Arylhydrazines and their salts are classical substrates in Fischer indole syntheses, enabling access to indole libraries.
• Cyclization to dihydropyrazoles/pyrazolines: Reaction with α,β-unsaturated carbonyl compounds furnishes pharmacologically relevant pyrazoline scaffolds.

The ortho-chloro substitution can modulate the reactivity of the hydrazine nitrogen and influence the electronic properties of the resulting heterocyclic products, enabling fine-tuning of biological and physicochemical profiles.

Preparation and Reaction Tips

Freeing the base: Because the compound is supplied as the dihydrochloride salt, reactions requiring the free hydrazine base should include a neutralization step. Treat the salt with an aqueous base (e.g., sodium carbonate or dilute sodium hydroxide), then extract with a suitable organic solvent, or use in situ generation in the reaction mixture where applicable.

Solubility: The dihydrochloride salt is generally soluble in polar protic solvents such as water, methanol, and ethanol. Solubility in aprotic solvents (DMF, DMSO) is typically lower; always verify experimentally with your specific lot.

Moisture control: Weigh and transfer the compound under dry conditions where possible. Extended exposure to atmospheric moisture can degrade the compound or cause caking. Use desiccant-sealed vials and return unused material promptly to storage.

Reaction monitoring: Thin-layer chromatography (TLC) and HPLC are effective tools for monitoring conversion in condensation reactions involving this reagent. Use ninhydrin or other amine-reactive stains for TLC visualization.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies [(2-chlorophenyl)methyl]hydrazine dihydrochloride under SKU C177042. Each lot is accompanied by a Certificate of Analysis (CoA) confirming identity and purity. Researchers are encouraged to request the CoA and SDS before placing an order or commencing experimental work.

Ordering: Visit the Aladdin Scientific website and search by SKU C177042 or by IUPAC name to access current stock availability, pricing, pack sizes, and lead times. Contact the Aladdin customer service team for bulk quotations, custom packaging, or technical inquiries.

Specification grade: Confirm the purity specification suitable for your application—standard reagent grade is appropriate for most synthetic chemistry workflows; higher purity grades may be required for sensitive analytical or biological assay development.

Frequently asked questions

What is [(2-chlorophenyl)methyl]hydrazine dihydrochloride used for?

It is primarily used as a synthetic intermediate in organic and medicinal chemistry for the preparation of nitrogen-containing heterocycles such as pyrazoles, pyrazolines, hydrazones, and indoles. These scaffolds are valuable in pharmaceutical research and agrochemical development.

Why is this compound supplied as a dihydrochloride salt rather than the free base?

Free hydrazines are generally susceptible to oxidation and are hygroscopic, making them difficult to handle and store. Converting to the dihydrochloride salt improves chemical stability, extends shelf life, and simplifies weighing and handling in the laboratory.

How should I handle and store C177042 safely?

Handle in a fume hood wearing appropriate PPE (nitrile gloves, lab coat, safety goggles). Store in a tightly sealed container in a cool, dry, well-ventilated area away from oxidizers and moisture. Always consult the current SDS for complete safety information before use.

How can I release the free hydrazine base from the dihydrochloride salt?

Treat an aqueous solution of the dihydrochloride salt with a suitable base such as sodium carbonate or dilute sodium hydroxide to neutralize the hydrochloride salts. The liberated free base can then be extracted into an organic solvent or generated in situ within the reaction mixture.

Where can I order [(2-chlorophenyl)methyl]hydrazine dihydrochloride?

You can order it directly from Aladdin Scientific using SKU C177042 via the Aladdin website. Contact the customer service team for pricing, available pack sizes, bulk quotations, and technical support.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for hydrazine chemistry and heterocycle synthesis.)
2. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed. Wiley-Blackwell. (Reference for pyrazole and indole synthesis from hydrazine derivatives.)
3. Aladdin Scientific. Certificate of Analysis, Product C177042, [(2-chlorophenyl)methyl]hydrazine dihydrochloride. (Lot-specific purity and characterization data; contact Aladdin for current CoA.)

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