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A10226 2-(Chloromethyl)pyridine hydrochloride, 98%

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

Stock No. Size Price ($) Quantity Availability
A10226-06 5g 31.00
A10226-14 25g 92.30
A10226-22 100g 258.00
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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°
Storage & Sensitivity
Hygroscopic. Store under Nitrogen. Ambient temperatures.
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: 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

Other References

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

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