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

Uses

Used in Pharmaceutical Industry:
2-(Chloromethyl)quinoline is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of diverse compounds with potential medicinal properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(Chloromethyl)quinoline is utilized as a precursor in the synthesis of various agrochemicals, including pesticides and herbicides. Its versatility in chemical reactions enables the production of effective compounds for crop protection and management.
As a Hazardous Chemical:
2-(Chloromethyl)quinoline is used as a reference for safety protocols and handling procedures in laboratories and industrial settings. Its classification as a hazardous chemical highlights the importance of proper storage, usage, and disposal to minimize health and environmental risks.

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 
• 613-53-6 2-tribromomethyl-quinoline 
• 91-63-4 2-methylquinoline 
• 87-90-1 trichloroisocyanuric acid 
• 540-38-5 p-Iodophenol 
• 3747-74-8 2-(chloromethyl)quinoline monohydrochloride 
• 19575-07-6 quinoline-2-carboxylic acid methyl ester 
• 60483-07-0 acetic acid quinolin-2-ylmethyl ether 
• 1076-28-4 2-methylquinoline N-oxide 
• 98-59-9 p-toluenesulfonyl chloride 
• 74405-07-5 4-chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine 
• 4032-53-5 2-trichloromethylquinoline 
• 109-63-7 trifluoroborane diethyl ether 

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.

N -Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N -chlorosuccinimide

The direct chlorination of C-H bonds has received considerable attention in recent years. In this work, a metal-free protocol for hydrocarbon C-H bond chlorination with commercially available N-chlorosuccinimide (NCS) catalyzed by N-hydroxyphthalimide (NHPI) with 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) functioning as an external radical initiator is presented. Aliphatic and benzylic substituents and also heteroaromatic ones were found to be well tolerated. Both the experiments and theoretical analysis indicate that the reaction goes through a process wherein NHPI functions as a catalyst rather than as an initiator. On the other hand, the hydrogen abstraction of the C-H bond conducted by a PINO species rather than the highly reactive N-centered radicals rationalizes the high chemoselectivity of the monochlorination obtained by this protocol as the latter is reactive towards the C(sp3)-H bonds of the monochlorides. The present results could hold promise for further development of a nitroxy-radical system for the highly selective functionalization of the aliphatic and benzylic hydrocarbon C-H.

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.

NOVEL INHIBITOR COMPOUNDS OF PHOSPHODIESTERASE TYPE 10A

The present invention relates to compounds of the formula (I), the N-oxides, tautomers, the prodrugs and the pharmaceutically acceptable salts thereof. In formula I the variables Het, A, X, Y, Z, R1, R2, R3, R4, R5 and Q are as defined in the claims. The compounds of the formula I, the N-oxides, tautomers, the prodrugs and the pharmaceutically acceptable salts thereof are inhibitors of phosphodiesterase type 10A. Thus, the invention also relates to the use of the compounds of the formula I, the N-oxides, tautomers, the prodrugs and the pharmaceutically acceptable salts thereof for the manufacture of a medicament and which thus are suitable for treating or controlling of medical disorders selected from neurological disorders and psychiatric disorders, for ameliorating the symptoms associated with such disorders and for reducing the risk of such disorders.

NOVEL INHIBITOR COMPOUNDS OF PHOSPHODIESTERASE TYPE 10A

The present invention relates to novel carboxamide compounds, pharmaceutical compositions containing them, and their use in therapy. The compounds possess valuable therapeutic properties and are particularly suitable for treating or controlling medical disorders selected from neurological disorders and psychiatric disorders, for ameliorating the symptoms associated with such disorders and for reducing the risk of such disorders

Synthesis of new chiral 2-functionalized-1,2,3,4-tetrahydroquinoline derivatives via asymmetric hydrogenation of substituted quinolines

The asymmetric hydrogenation of a series of quinolines substituted by a variety of functionalized groups linked to the C2 carbon atom is providing access to optically enriched 2-functionalized 1,2,3,4-tetrahydroquinolines in the presence of in situ generated catalysts from [Ir(cod)Cl]2, a bisphosphine, and iodine. The enantioselectivity levels were as high as 96% ee.

BICYCLIC HETEROARYL COMPOUNDS AS PDE10 INHIBITORS

The invention pertains to tricyclic heteraaryi compounds that serve as effective phosphodiesterase (PDE) inhibitors. The invention also relates to compounds which are selective inhibitors of PDE 10. The invention further relates to pharmaceutical compositions comprising such compounds; and the use of such compounds in methods for treating certain central nervous system (CNS) or other disorders. The invention relates also to methods for treating neurodegenerative and psychiatric disorders, for example psychosis and disorders comprising deficient cognition as a symptom.

Benz(2-heteroaryl)cyanoximes and their Tl(i) complexes: New room temperature blue emitters

A series of five 2-heteroarylcyanoximes such as: α-oximino-(2- benzimidazolyl)acetonitrile (HBIHCO), α-oximino-(N-methy-l-2- benzimidazolyl)acetonitrile (HBIMCO), α-oximino-(2-benzoxazolyl) acetonitrile (HBOCO), α-oximino-(2-benzothiazolyl)acetonitrile (HBTCO) and α-oximino-(2-quinolyl)acetonitrile (HQCO) and their monovalent thallium(i) complexes were synthesized and characterized using spectroscopic methods (1H, 13C NMR, IR, UV-visible, mass-spectrometry) and X-ray analysis. The HBIMCO (as monohydrate) adopts planar trans-anti configuration in the solid state. The crystal structure of "HBOCO" revealed the presence of nitroso anion a, BOCO-, and protonated oxime cation b, H2BOCO+, that form a H-bonded dimer in the unit cell. Both molecules adopt planar structures, but different configurations: cis-anti in the molecule a, and trans-anti for b. This is the first reported case of a zwitterionic pair in oximes and the coexistence of the two geometrical cis/trans isomers in the same crystal. All 2-heteroarylcyanoximes form yellow anions upon deprotonation, which exhibit significant negative solvatochromism in solution. Heterogeneous reactions between hot aqueous solutions of Tl 2CO3 and solid protonated 2-heteroarylcyanoximes HL afford yellow TlL. The crystal structure of Tl(BTCO) shows the formation of centrosymmetrical dimers, which connect with each other to form a double-stranded one-dimensional coordination polymer. The oxygen atom of the oxime group acts as a bridge between the three different Tl(i) centers. The anion is non-planar and adopts a trans-anti configuration in the complex. The polymeric motif in the complex represents a ladder-type structure. Staggered π-π interactions between benzothiazolyl groups provide additional stabilization of the structure. Both organic ligands and their Tl(i) complexes exhibit strong room temperature blue emission in the solid state.

Therapeutic uses of tri-aryl acid derivatives

The use of triaryl acid derivatives of formula (I) and their pharmaceutical compositions as PPAR ligand receptor binders. The PPAR ligand receptor binders of this invention are useful as agonists or antagonists of the PPAR receptor.