I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
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).
Gefahrenhinweise (EU): H302-H314-H318
Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.
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.