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1822-51-1 - 4-(Chloromethyl)pyridine hydrochloride, 98% - 4-Picolyl chloride hydrochloride - A12859 - Alfa Aesar

A12859 4-(Chloromethyl)pyridine hydrochloride, 98%

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

Size Price ($) Quantity Availability
5g 26.06
25g 80.34
100g 242.00
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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°
Sensitivity
Hygroscopic
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: H301-H311-H317-H314-H318

Toxic if swallowed. Toxic in contact with skin. May cause an allergic skin reaction. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P261-P280-P301+P310-P303+P361+P353-P305+P351+P338-P361-P301+P330+P331-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. 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. Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
3689154
Hazard Class
8
Packing Group
III
Harmonized Tariff Code
2933.39
TSCA
No

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