607-31-8

Basic information

• Product Name: 4-Methoxyquinoline
• Synonyms: 4-Methoxyquinoline
• CAS NO: 607-31-8
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: -0
• Product Categories: pharmacetical
• Mol File: 607-31-8.mol

Chemical Properties

• Melting Point: 41°C
• Boiling Point: 284.68°C (rough estimate)
• Flash Point: 89.7 °C
• Appearance: /
• Density: 1.1202 (rough estimate)
• Vapor Pressure: 0.0444mmHg at 25°C
• Refractive Index: 1.6070 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 6.37±0.13(Predicted)
• CAS DataBase Reference: 4-Methoxyquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxyquinoline(607-31-8)
• EPA Substance Registry System: 4-Methoxyquinoline(607-31-8)

Safety Data

• Hazardous Substances Data: 607-31-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Methoxyquinoline is used as a reactant in the synthesis of hybrid quinoline-4-yloxadiazoles/oxathiadiazoles, which are potent antifungal agents. These agents are valuable in the development of new drugs to combat fungal infections, offering an alternative to conventional antifungal treatments.

InChI:InChI=1/C10H9NO/c1-12-10-6-7-11-9-5-3-2-4-8(9)10/h2-7H,1H3

Upstream product

• 67-56-1 methanol 
• 611-35-8 4-chloroquinoline 
• 124-41-4 sodium methylate 
• 3741-15-9 4-nitroquinoline 
• 14547-98-9 4-methoxyquinoline-N-oxide 
• 611-36-9 quinolin-4-ol 
• 26707-52-8 7-chloro-4-methoxyquinoline 
• 865-33-8 potassium methanolate 
• 3964-04-3 4-bromoquinoline 
• 74-88-4 methyl iodide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 86-98-6 4,7-dichloroquinoline 
• 15733-83-2 4-methoxyquinoline-2-carboxylic acid 
• 65148-06-3 N-((4-methylphenyl)sulfonyl)-N-phenyl-beta-alanine 

Downstream Products

• 83-54-5 1-methyl-4-quinolone 
• 14547-98-9 4-methoxyquinoline-N-oxide 

Relevant articles and documents

Tautomerism of 4-hydroxy-4(1H) quinolon

The tautomerism of 4-Hydroxy-4(1H) quinolon I was studied using infrared spectroscopy, 1H,13C NMR spectroscopy and X-ray crystallography. The keto-form of I is favored in the crystal form and at room temperature in polar solutions like water and dimethylsulfoxide.

Deuterated Aryl Alkyl Ethers Synthesis via Nucleophilic Etherification of Aryl Alkyl Ethers and Thioethers with Deuterated Alcohols

A transition-metal-free etherification protocol that is capable of synthesizing deuterated ethers is described. A wide range of aryl alkyl ethers and thioethers were suitable for this transformation owing to the mild reaction conditions. Besides, a series of sterically bulky deuterated alcohols were successfully incorporated into cyano-substituted arenes. The results of mechanistic studies suggested this reaction might take place via nucleophilic aromatic substitution pathway.

Discovery of MK-8318, a Potent and Selective CRTh2 Receptor Antagonist for the Treatment of Asthma

A novel series of tricyclic tetrahydroquinolines were identified as potent and selective CRTh2 receptor antagonists. The agonism and antagonism switch was achieved through structure-based drug design (SBDD) using a CRTh2 receptor homologue model. The challenge of very low exposures in pharmacokinetic studies was overcome by exhaustive medicinal chemistry lead optimization through focused SAR studies on the tricyclic core. Further optimization resulted in the identification of the preclinical candidate 4-(cyclopropyl((3aS,9R,9aR)-7-fluoro-4-(4-(trifluoromethoxy)benzoyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]quinolin-9-yl)amino)-4-oxobutanoic acid (15c, MK-8318) with potent and selective CRTh2 antagonist activity and a favorable PK profile suitable for once daily oral dosing for potential treatment of asthma.

PYRAZOLE DERIVATIVES AS MALT1 INHIBITORS

Disclosed are compounds, compositions and methods for treating of diseases, syndromes, conditions, and disorders that are affected by the modulation of MALT1. Such compounds are represented by Formula (I) as follows: wherein R1, R2, R3, R4, R5, R6, R5, G1, and G2 are defined herein.

General and Practical Potassium Methoxide/Disilane-Mediated Dehalogenative Deuteration of (Hetero)Arylhalides

Herein we describe a general, mild and scalable method for deuterium incorporation by potassium methoxide/hexamethyldisilane-mediated dehalogenation of arylhalides. With CD3CN as a deuterium source, a wide array of heteroarenes prevalent in pharmaceuticals and bearing diverse functional groups are labeled with excellent deuterium incorporation (>60 examples). The ipso-selectivity of this method provides precise access to libraries of deuterated indoles and quinolines. The synthetic utility of our method has been demonstrated by the incorporation of deuterium into complex natural and drug-like compounds.

QUINOLINE DERIVATIVES AS SMO INHIBITORS

Disclosed are quinoline derivatives as hedgehog pathway inhibitors, especially as SMO inhibitors. Compounds of the present invention can be used in treating diseases relating to hedgehog pathway including cancer.

N-Methylimidazole-mediated synthesis of aryl alkyl ethers under microwave irradiation and solvent free conditions

A microwave-assisted three-component reaction was established for the synthesis of aryl alkyl ethers. The reaction was performed under solvent-free conditions in the presence of N-methylimidazole and dialkyl acetylene-dicarboxylate to furnish a novel approach to O-alkylation of phenol derivatives in high yield.

Chiral helical oligotriazoles: New class of anion-binding catalysts for the asymmetric dearomatization of electron-deficient N -heteroarenes

Helical chirality and selective anion-binding processes are key strategies used in nature to promote highly enantioselective chemical reactions. Although enormous efforts have been made to develop simple helical chiral systems and thus open new possibilities in asymmetric catalysis and synthesis, the efficient use of synthetic oligo- and polymeric helical chiral catalysts is still very challenging and rather unusual. In this work, structural unique chiral oligotriazoles have been developed as C-H bond-based anion-binding catalysts for the asymmetric dearomatization of N-heteroarenes. These rotational flexible catalysts adopt a reinforced chiral helical conformation upon binding to a chloride anion, allowing high levels of chirality transfer via a close chiral anion-pair complex with a preformed ionic substrate. This methodology offers a straightforward and potent entry to the synthesis of chiral (bioactive)heterocycles with added synthetic value from simple and abundant heteroarenes.

Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N -Heterocycles from n -oxides

A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of copper catalysis and activation by lithium fluoride or magnesium chloride. The utility of this method for the late-stage modification of complex N-heterocycles is exemplified by facile syntheses of new structural analogues of several antimalarial, antimicrobial, and fungicidal agents.

Gold(I)-catalyzed protodecarboxylation of (Hetero)aromatic carboxylic acids

Readily available, inexpensive and easy to handle, carboxylic acids have been shown to be very effective, greener coupling partners compared to costly organometallic reagents for the formation of C-C bonds. The use of well-defined gold complexes furnished 3 in slightly better yield with butyric acid, and in quantitative yield with adamantane-1-carboxylic acid. All reactions reached completion within 16 h. As with silver systems, this reactivity trend highlights, as previously observed, the benefits of potential coordinating groups in the ortho position to the gold binding site, which possibly facilitate the decarboxylation step. Additional reaction time and increased temperatures were necessary to afford the gold aryl products in satisfactory yields. Yet, some substrates such as 2-nitrobenzoic acids reacted poorly and could only be transformed in 50% yield.