4-(chloromethyl)pyridine hydrochloride

• ChemBase ID: 11758
• Molecular Formular: C6H7Cl2N
• Molecular Mass: 164.03248
• Monoisotopic Mass: 162.99555459
• SMILES: ClCc1ccncc1.Cl
• Canonical SMILES: ClCc1ccncc1.Cl
• InChI: InChI=1S/C6H6ClN.ClH/c7-5-6-1-3-8-4-2-6;/h1-4H,5H2;1H
• InChIKey: ZDHKVKPZQKYREU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(chloromethyl)pyridine hydrochloride
• IUPAC Traditional name: 4-(chloromethyl)pyridine hydrochloride
• Synonyms: 4-(Chloromethyl)pyridine hydrochloride; 4-Chloromethylpyridine hydrochloride; 4-Picolyl chloride hydrochloride; 4-(Chloromethyl)pyridine hydrochloride; 4-(氯甲基)吡啶盐酸盐; 4-吡啶甲基氯 盐酸盐; 4-(氯甲基)吡啶 盐酸盐

Database IDs

• CAS Number: 1822-51-1
• EC Number: 217-350-7
• MDL Number: MFCD00012826
• Beilstein Number: 3689154
• PubChem SID: 24898533; 160975065
• PubChem CID: 74570

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.2329248
• LogD (pH = 7.4): 1.3411909
• Log P: 1.3428155
• Molar Refractivity: 33.768 cm^3
• Polarizability: 13.085412 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 166 - 173°C; 166-171°C; 166-173 °C(lit.); 169-171°C
• Hydrophobicity(logP): 1.207

Safety Information

• Storage Warning: Corrosive; Hygroscopic; HYGROSCOPIC, CORROSIVE
• European Hazard Symbols: Corrosive (C); X
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3; III
• Risk Statements: 21/22-34-43; 34
• Safety Statements: 24-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H317-H314-H318; H314
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (AT); 95%; 97%; 98%
• Grade: purum
• Salt Data: HCl
• Empirical Formula (Hill Notation): C6H6ClN · HCl

DETAILS

Sigma Aldrich - P43807

Packaging
10, 100 g in glass bottle

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.