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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%

Numéro de CAS
1822-51-1
Synonymes
4-Picolyl chloride hydrochloride

Conditionnement Prix ($) Quantité Disponibilité
5g 25,80
25g 79,60
100g 277,00
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4-(Chloromethyl)pyridine hydrochloride, 98%

MDL
MFCD00012826
EINECS
217-350-7

Propriétés chimiques

Formule
C6H62N•HCl
Poids moleculaire
164.04
Point de fusion
166-171°
Sensibilité
Hygroscopic
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H301-H311-H314-H318-H317

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

Mentions de prudence: P260u-P301+P310a-P303+P361+P353-P305+P351+P338-P405-P501a

IF SWALLOWED: 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
3689154
Classe de danger
8
Groupe d'emballage
III
Code tarifaire harmonisé
2933.39
TSCA
No

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