4-(Chloromethyl)pyridine hydrochloride

• Catalog No.: A12859
• CAS Number: 1822-51-1
• M. F.: C6H7Cl2N
• M. W.: 164.03248
• Purity: 98%

SYNONYMS

• Title: 4-(氯甲基)吡啶盐酸盐
• IUPAC name: 4-(chloromethyl)pyridine hydrochloride
• IUPAC Traditional name: 4-(chloromethyl)pyridine hydrochloride
• Synonyms: 4-Picolyl chloride hydrochloride

DATABASE IDS

• EC Number: 217-350-7
• Beilstein Number: 3689154
• CAS Number: 1822-51-1
• MDL Number: MFCD00012826

PROPERTIES

• Purity: 98%
• Melting Point: 166-171°C
• GHS Hazard statements: H301-H311-H317-H314-H318
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A
• Risk Statements: 21/22-34-43
• Safety Statements: 24-26-36/37/39-45
• Storage Warning: Hygroscopic
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN3261
• Packing Group: III

REFERENCES

• 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.