2-(chloromethyl)quinoline hydrochloride

• ChemBase ID: 87238
• Molecular Formular: C10H9Cl2N
• Molecular Mass: 214.09116
• Monoisotopic Mass: 213.01120465
• SMILES: n1c2c(ccc1CCl)cccc2.Cl
• Canonical SMILES: ClCc1ccc2c(n1)cccc2.Cl
• InChI: InChI=1S/C10H8ClN.ClH/c11-7-9-6-5-8-3-1-2-4-10(8)12-9;/h1-6H,7H2;1H
• InChIKey: WDETYCRYUBGKCE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(chloromethyl)quinoline hydrochloride
• IUPAC Traditional name: 2-(chloromethyl)quinoline hydrochloride
• Synonyms: 2-(Chloromethyl)quinoline hydrochloride; α-Chloroquinaldine hydrochloride; 2-(Chloromethyl)quinoline hydrochloride; alpha-Chloroquinaldine hydrochloride; α-氯喹哪啶 盐酸盐; 2-(氯甲基)喹啉 盐酸盐

Database IDs

• CAS Number: 3747-74-8
• EC Number: 223-145-3
• MDL Number: MFCD00012734
• Beilstein Number: 3565832
• PubChem SID: 24855111; 24892578; 162074353
• PubChem CID: 3083823

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.7950428
• LogD (pH = 7.4): 2.7995565
• Log P: 2.7996144
• Molar Refractivity: 49.324 cm^3
• Polarizability: 20.624895 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 183 - 187°C; 183-187 °C(lit.); 184-187°C; 184-189 °C; 184-190°C
• Hydrophobicity(logP): 2.591

Safety Information

• Storage Warning: Harmful/Irritant
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-38-41-43; 37/38-41-43
• Safety Statements: 24-26-37/39; 26-36/37/39
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H317-H318; H318-H315-H317-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥97.0% (AT); 95%; 97%
• Grade: purum
• Empirical Formula (Hill Notation): C10H8ClN · HCl

DETAILS

Sigma Aldrich - C57103

Packaging
25 g in poly bottle
5 g in glass bottle

REFERENCES

• As with 2-(Chloromethyl)pyridine hydrochloride, A10226, lithiation of the free base can be effected at the methylene group. Quinolylaziridines are formed on subsequent reaction with imines: J. Org. Chem., 60, 2279 (1995).
• The free base has been used in the protection of OH groups as 2-quinolinylmethyl (Qm) ethers which can be cleaved by aerial oxidation in the presence of Cu(II): J. Org. Chem., 55, 5344 (1990), or by photolysis: Tetrahedron, 48, 10563 (1992). The protection of thiols has also been reported, as the Qm thioethers, which can be cleaved with Fe(III) or Cu(II): Chem. Lett., 803 (1993).