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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-H318
Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.