2-(chloromethyl)pyridine hydrochloride

• ChemBase ID: 11759
• Molecular Formular: C6H7Cl2N
• Molecular Mass: 164.03248
• Monoisotopic Mass: 162.99555459
• SMILES: c1cc(ncc1)CCl.Cl
• Canonical SMILES: ClCc1ccccn1.Cl
• InChI: InChI=1S/C6H6ClN.ClH/c7-5-6-3-1-2-4-8-6;/h1-4H,5H2;1H
• InChIKey: JPMRGPPMXHGKRO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(chloromethyl)pyridine hydrochloride
• IUPAC Traditional name: 2-(chloromethyl)pyridine hydrochloride
• Synonyms: 2-(Chloromethyl)pyridine hydrochloride; 2-(Chloromethyl)pyridine hydrochloride; 2-Chloromethylpyridine hydrochloride; 2-Picolyl chloride hydrochloride; 2-吡啶甲基氯 盐酸盐; 2-氯甲基吡啶 盐酸盐; 2-(氯甲基)吡啶盐酸盐

Database IDs

• CAS Number: 6959-47-3
• EC Number: 230-149-9
• MDL Number: MFCD00012811
• Beilstein Number: 3689155
• PubChem SID: 24850002; 160975066; 24855223
• PubChem CID: 23392

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.4065783
• LogD (pH = 7.4): 1.4240595
• Log P: 1.4242873
• Molar Refractivity: 33.2458 cm^3
• Polarizability: 13.086979 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 119-125°C; 120-124 °C; 120-124 °C(lit.); 120-124°C

Safety Information

• Storage Warning: Harmful/Corrosive/Irritant/Hygroscopic/Store under Argon; Hygroscopic; HYGROSCOPIC, CORROSIVE
• RTECS: US6825000
• 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; 22-34
• Safety Statements: 24-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H317-H314-H318; H302-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

Product Information

• Purity: ≥98.0% (AT); 97%; 98%
• Grade: purum
• Salt Data: HCl
• Empirical Formula (Hill Notation): C6H6ClN · HCl

DETAILS

Sigma Aldrich - 162701

Packaging
5, 25, 100 g in glass bottle

REFERENCES

• The free base has also been used for the protection of OH groups as 2-picolyl derivatives, relatively stable to acid (HF, TFA) but selectively cleaved by electrolytic reduction: Acta Chem. Scand. B, B37, 475 (1983); J. Chem. Res. (Synop.), 22 (1977).
• For a study of the base-catalyzed alkylation of p-t-butylcalix[5]arene, see: J. Org. Chem., 61, 2407 (1996).
• The free base, generated from the hydrochloride with aqueous OH^-, can be metallated (LDA, -78^o) at the methylene group. Subsequent reaction with a ketone provides a route to otherwise inaccessible pyridyloxiranes: Tetrahedron Lett., 35, 3175 (1994). Similarly, reaction of the lithio derivative with an imine gives a pyridylaziridine, generally in good yield: J. Org. Chem., 60, 2279 (1995).