4377-41-7

Basic information

• Product Name: 2-(chloromethyl)quinoline
• Synonyms: 2-(chloromethyl)quinoline;alpha-Chloroquinaldine;NSC 158442
• CAS NO: 4377-41-7
• Molecular Formula: C₁₀H₈ClN
• Molecular Weight: 177.63022
• EINECS: 224-479-2
• Mol File: 4377-41-7.mol
• Article Data: 32

Chemical Properties

• Melting Point: 56.5-57.5℃
• Boiling Point: 288.8 °C at 760 mmHg
• Flash Point: 155.9 °C
• Appearance: /
• Density: 1.229 g/cm³
• Storage Temp.: 2-8°C
• PKA: 3.48±0.48(Predicted)
• CAS DataBase Reference: 2-(chloromethyl)quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(chloromethyl)quinoline(4377-41-7)
• EPA Substance Registry System: 2-(chloromethyl)quinoline(4377-41-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 4377-41-7(Hazardous Substances Data)

Usage

General Description

2-(Chloromethyl)quinoline is a chemical compound with the molecular formula C10H8ClN. It is a chlorinated derivative of quinoline, which is a heterocyclic aromatic compound. This chemical is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals. It is a white to pale yellow solid with a strong odor, and it is soluble in organic solvents such as ether and chloroform. 2-(Chloromethyl)quinoline is classified as a hazardous chemical, and precaution should be taken when handling and storing it due to its potential to cause skin and eye irritation upon contact.

InChI:InChI=1/C10H8ClN/c11-7-9-6-5-8-3-1-2-4-10(8)12-9/h1-6H,7H2

Upstream product

• 1780-17-2 quinolin-2-ylmethanol 
• 5632-15-5 quinolin-2-ylmethylbromide 
• 1076-28-4 2-methylquinoline N-oxide 
• 109-63-7 trifluoroborane diethyl ether 
• 68-12-2 N,N-dimethyl-formamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 4032-53-5 2-trichloromethylquinoline 
• 613-53-6 2-tribromomethyl-quinoline 
• 74405-07-5 4-chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine 
• 60483-07-0 acetic acid quinolin-2-ylmethyl ether 
• 540-38-5 p-Iodophenol 
• 3747-74-8 2-(chloromethyl)quinoline monohydrochloride 
• 19575-07-6 quinoline-2-carboxylic acid methyl ester 
• 91-63-4 2-methylquinoline 

Downstream Products

• 101274-73-1 2-(phenylthiomethyl)quinoline 
• 132649-29-7 2-[(4-chloro-phenylsulfanyl)-methyl]-quinoline 
• 1780-17-2 quinolin-2-ylmethanol 
• 107813-50-3 2-(4-nitro-phenoxymethyl)-quinoline 
• 5470-96-2 quinoline 2-carbaldehyde 
• 129492-22-4 (1R-(1α,2β,5α))-2-(((5-methyl-2-(1-methylethyl)cyclohexyl)oxy)methyl)quinoline 
• 111974-54-0 3-<(2-quinolinyl)methoxy>nitrobenzene 
• 119481-56-0 2-(Quinolin-2-ylmethylsulfanyl)-phenylamine 
• 114497-66-4 2-[4-(Quinolin-2-yl-methoxy)phenyl]-acetonitrile 
• 107813-60-5 3-(Quinolin-2-ylmethoxy)-benzonitrile 
• 125439-41-0 4-(2-quinolinylmethoxy)phenyl benzoate 
• 119481-55-9 3-(Quinolin-2-ylmethylsulfanyl)-phenylamine 
• 123723-93-3 4-(quinolin-2-yl-methoxy)phenyl-acetic acid methyl ester 
• 107813-90-1 2-((3-butoxyphenoxy)methyl)quinoline 

Relevant articles and documents

Rapid and Effective Reaction of 2-Methylpyridin-N-oxides with Triphosgene via a [3,3]-Sigmatropic Rearrangement: Mechanism and Applications

A facile and effective synthesis of 2-chloromethylpyridines was developed by a one-pot reaction of 2-alkylpyridin-N-oxides and triphosgene at room temperature. As starting materials, N-oxides of 2-alkylpyridine derivatives, including 2-alkylpyridines, 2-methyl quinolines, and phenanthroline, can react rapidly with triphosgene in the presence of triethylamine, affording 2-chloromethylpyridines in good to excellent yields (52-95%). Using the 2-methylquinoline substrate for the mechanistic study, it has been well demonstrated that the chlorination reaction undergoes a [3,3]-sigmatropic rearrangement, which can be observed as a reversible process by monitoring the intermediates. Moreover, the chlorination reaction can be used to construct a rapid and sensitive fluorescent probe for the detection of phosgene.

Copper(II) catalyzed heterobenzylic C(sp3)-H activation: Two efficient halogenation methodologies towards heterobenzyl halides

Two practical and simple synthetic methodologies towards various heterobenzyl halides were developed. A series of 2-halomethylquinolines were readily prepared by the one-pot reaction of 2-methylquinolines with CuX (X = I, Br, Cl) and TBHP in CH3CN. A large variety of heterobenzyl iodides, including 2-iodomethylquinolines, 2-iodomethylquinoxalines, 2-iodiomethylbenzooxazole, and 2-iodiomethylbenzothiazole, were efficiently synthesized by one-pot reaction of 2-methylheterocycles with iodine in the presence of CuSO4·5H2O in CH3CN.

Microwave-assisted α-halogenation of 2-methylquinolines with tetrabutylammonium iodide and 1,2-dichloroethane (1,2-dibromoethane)

A simple and efficient methodology permitting the halogenation of 2-methylquinolines into 2-(chloromethyl)quinolines or 2-(bromomethyl)quinolines in the tetrabutylammonium iodide and 1,2-dichloroethane (1,2-dibromoethane) system has been developed for the first time. The halogenation can be rapidly completed with good to excellent yields and high selectivity under microwave irradiation.