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2-(Chloromethyl)pyridine hydrochloride was used as reagent in base catalyzed alkylation of p-tert-butylcalixarene and p-tert-butylcalixarene in DMF. It was used in the synthesis of Gd3+ diethylenetriaminepentaacetic acid bisamide complex, a Zn2+-sensitive magnetic resonance imaging contrast agent.
Neri P and Pappalardo S. Functionalization of p-tert-butylcalix  arene by alkylation with 2-(chloromethyl) pyridine hydrochloride. J. Org. Chem. 1993, 58,(5), 1048-53.
Pappalardo S and Ferguson G. Functionalization of p-tert-Butylcalix  arene by Alkylation with 2-(Chloromethyl) pyridine Hydrochloride. J. Org. Chem. 1996, 61,(7),2407-12.
Hanaoka K, et al. Selective sensing of zinc ions with a novel magnetic resonance imaging contrast agent. J. Chem. Soc. Perkin Trans. 2001, 9,1840-43.
The free base, generated from the hydrochloride with aqueous OH-, can be metallated (LDA, -78o) at the methylene group. Subsequent reaction with a ketone provides a route to otherwise inaccessible pyridyloxiranes: Tetrahedron Lett., 35, 3175 (1994). Similarly, reaction of the lithio derivative with an imine gives a pyridylaziridine, generally in good yield: J. Org. Chem., 60, 2279 (1995).
The free base has also been used for the protection of OH groups as 2-picolyl derivatives, relatively stable to acid (HF, TFA) but selectively cleaved by electrolytic reduction: Acta Chem. Scand. B, B37, 475 (1983); J. Chem. Res. (Synop.), 22 (1977).
For a study of the base-catalyzed alkylation of p-t-butylcalixarene, see: J. Org. Chem., 61, 2407 (1996).
Hazard Statements: H302-H314-H335
Harmful if swallowed. Causes severe skin burns and eye damage. May cause respiratory irritation.
Precautionary Statements: P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant