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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%

CAS Number
6959-47-3
Synonyms
2-Picolyl chloride hydrochloride

Size Price ($) Quantity Availability
5g 29.07
25g 89.58
100g 255.44
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2-(Chloromethyl)pyridine hydrochloride, 98%

MDL
MFCD00012811
EINECS
230-149-9

Chemical Properties

Formula
C6H6ClN•HCl
Formula Weight
164.04
Melting point
120-124°
Sensitivity
Hygroscopic
Solubility
Soluble in water, acetone (10-50mg/ml), 95%ethanol (100mg/ml).

Applications

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.

Notes

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

Literature References

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H302

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

Precautionary Statements: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P301+P312-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. 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 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. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
3689155
Hazard Class
8
Packing Group
III
Harmonized Tariff Code
2933.39
TSCA
No
RTECS
US6825000

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