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6959-47-3 - 2-(Chloromethyl)pyridine hydrochloride, 98% - 2-Picolyl chloride hydrochloride - A10226 - Alfa Aesar

A10226 2-(Chloromethyl)pyridine hydrochloride, 98%

Codice CAS
6959-47-3
Sinonimi
2-Picolyl chloride hydrochloride

Dimensioni Prezzo ($) Quantità Disponibilità
5g 30,70
25g 93,20
100g 253,00
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2-(Chloromethyl)pyridine hydrochloride, 98%

MDL
MFCD00012811
EINECS
230-149-9

Proprietà chimiche

Formula
C6H6ClN•HCl
Peso formula
164.04
Punto di fusione
120-124°
Sensibilità
Hygroscopic
Solubilità
Soluble in water, acetone (10-50mg/ml), 95%ethanol (100mg/ml).

Applicazioni

2-(Chloromethyl)pyridine hydrochloride was used as reagent in base catalyzed alkylation of p-tert-butylcalix[6]arene and p-tert-butylcalix[5]arene in DMF. It was used in the synthesis of Gd3+ diethylenetriaminepentaacetic acid bisamide complex, a Zn2+-sensitive magnetic resonance imaging contrast agent.

Note

Hygroscopic store in inert gas Store away from strong oxidizing agents. keep container tightly closed. Store in cool, dry conditions in well sealed containers.

Letteratura

Neri P and Pappalardo S. Functionalization of p-tert-butylcalix [6] 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 [5] 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-butylcalix[5]arene, see: J. Org. Chem., 61, 2407 (1996).

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H302-H314-H318

Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.

Dichiarazioni precauzionali: 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.

Altri riferimenti

Beilstein
3689155
Classe di rischio
8
Gruppo di imballaggio
III
Codice tariffe armonizzato
2933.39
TSCA
No
RTECS
US6825000

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