Overview and Chemical Identity

3-(Chloromethyl)isoquinoline hydrochloride (SKU C194982) consists of an isoquinoline ring system — a nitrogen-containing bicyclic aromatic heterocycle — substituted with a –CH₂Cl group at the 3-position. The compound is supplied as its hydrochloride salt, which confers improved bench stability compared with the free base.

The reactive chloromethyl moiety behaves as a benzylic electrophile and is susceptible to displacement by a wide variety of nucleophiles including amines, thiols, alcohols, and stabilised carbanions, making this scaffold highly versatile in synthetic programmes targeting isoquinoline-containing pharmacophores.

Typical Synthetic Applications

N-Alkylation of amines and nitrogen heterocycles: The –CH₂Cl electrophile reacts smoothly with primary and secondary amines under mild base conditions to introduce the 3-isoquinolinylmethyl group, a motif found in several bioactive compound classes.

S-Alkylation of thiols and thioethers: Thiol nucleophiles react rapidly with benzylic chlorides; this reactivity is exploited in the preparation of thioether-linked isoquinoline conjugates and prodrug linkers.

O-Alkylation and ether synthesis: Phenols and alkoxides can be alkylated under standard Williamson conditions to afford isoquinolinylmethyl ethers.

Cross-coupling precursors: Although the chloromethyl group itself is not typically used in Pd-catalysed cross-coupling, the compound may serve as a precursor to organometallic or phosphonium intermediates used in further elaboration of the isoquinoline core.

Handling, Safety, and Storage

Reactivity hazards: As a benzylic chloride, this compound is a lachrymator and potential alkylating agent; handle in a well-ventilated fume hood wearing appropriate PPE (nitrile gloves, lab coat, safety glasses). Avoid inhalation of dust or aerosols.

Moisture sensitivity: The free chloromethyl group is susceptible to hydrolysis; keep the reagent in a tightly sealed container and minimise exposure to atmospheric moisture. The hydrochloride salt form mitigates — but does not eliminate — this sensitivity.

Recommended storage: Store at 2–8 °C (or as specified on the product label) in a cool, dry place away from light and incompatible materials (strong bases, oxidising agents). Always consult the current Safety Data Sheet (SDS) before use.

Waste disposal: Treat as halogenated organic waste according to local regulations. Do not pour down the drain.

Solution Preparation and Reaction Tips

Solubility: The hydrochloride salt is generally soluble in polar aprotic solvents such as DMF and DMSO, and in polar protic solvents such as methanol and water (to a degree). Solubility in diethyl ether and non-polar solvents is limited. When the free base is required, the hydrochloride may be liberated by treatment with aqueous base (e.g., K₂CO₃) followed by extraction into an organic solvent.

Base selection for alkylation reactions: For N-alkylation, K₂CO₃ in DMF or acetonitrile at room temperature to 60 °C is a common and reliable protocol. Cs₂CO₃ may be used for less reactive nucleophiles. Avoid strong aqueous bases that may promote hydrolysis of the –CH₂Cl group.

Reaction monitoring: TLC and LCMS are recommended for monitoring reaction progress given the polarity difference between starting material and product.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 3-(Chloromethyl)isoquinoline hydrochloride under SKU C194982. Purity specification and available pack sizes are listed on the product page; consult the Certificate of Analysis (CoA) supplied with each lot for confirmed analytical data including HPLC purity, NMR identity, and water content.

For bulk or custom quantities, please contact Aladdin Scientific's sales team. Volume pricing may be available for larger orders. This reagent is intended for research use only and is not for diagnostic or therapeutic use in humans or animals.