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A12859 4-(Chloromethyl)pyridine hydrochloride, 98%

CAS Number
1822-51-1
Synonyms
4-Picolyl chloride hydrochloride

Stock No. Size Price ($) Quantity Availability
A12859-06 5g 26.80
A12859-14 25g 81.70
A12859-22 100g 266.00
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4-(Chloromethyl)pyridine hydrochloride, 98%

MDL
MFCD00012826
EINECS
217-350-7

Chemical Properties

Formula
C6H62N•HCl
Formula Weight
164.04
Melting point
166-171°
Storage & Sensitivity
Hygroscopic. Ambient temperatures.
Solubility
Soluble in water (750 mg/ml at 20°C), soluble in 1N HCl (2.5%), DMSO, and methanol.

Applications

It finds its application as a reagent for protection of carboxyl termini of peptides as 4-picolyl esters, providing a polar 'handle' which aids in separation and purification of the peptide. The group can be introduced in the presence of a base, e.g. tetramethylguanidine, is stable to acid-catalyzed removal of Cbz protecting group and can be removed by base, Na in liquid ammonia or catalytic hydrogenolysis. It is also applied in conjunction with Amberlyst®15 resin in peptide synthesis. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Notes

Hygroscopic. Store away from oxidizing agents and bases. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

Hongwei Hou, et al. A novel coordination polymer [Co(NCS)2(bpms)2]n (bpms=1,2-bis(4-pyridylmethyl)disulfenyl): synthesis, crystal structure and third-order nonlinear optical properties.Inorganica Chimica Acta,2001,316(1-2), 140-144.

Ping Zhou, et al.TA new efficient synthesis of 3-(4-pyridinyl)methylindoles.Tetrahedron Letters.,2001,42(42), 7333-7335.

Reagent for protection of carboxyl termini of peptides as 4-picolyl esters, providing a polar 'handle' which aids in separation and purification of the peptide. The group can be introduced in the presence of a base, e.g. tetramethylguanidine, is stable to acid-catalyzed removal of Cbz protecting group and can be removed by base, Na in liquid ammonia or catalytic hydrogenolysis: J. Chem. Soc. (C), 1911 (1969); 46, 50 (1971). For use in conjunction with Amberlyst®15 resin in peptide synthesis, see: J. Chem. Soc., Chem. Commun., 1057 (1971). For an alternative means of introduction, see 4-Pyridinemethanol, A14698.

As its free base, has been used for the protection of OH groups as 4-picolyl derivatives, relatively stable to acid (HF, TFA) but selectively cleaved by electrolytic reduction: J. Chem. Soc., Chem. Commun., 1123 (1972); Acta Chem. Scand. B, B37, 475 (1983); J. Chem. Res. (Synop.), 22 (1977). For use in the protection of the hydroxyl-substituted amino acids serine and threonine as their 4-picolyl ethers, see: J. Org. Chem., 53, 5386 (1988). In this case the group was cleaved by hydrogenolysis in AcOH. See also Appendix 6.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H314

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

Precautionary Statements: P260-P264b-P270-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. 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
3689154
Hazard Class
8
Packing Group
III
Harmonized Tariff Code
2933.39
TSCA
No

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