491-35-0

Basic information

• Product Name: Lepidine
• Synonyms: 4-methyl-quinolin;Cincholepidine;gamma-Methylquinoline;Lepidin;-Methylquinoline;Quinoline,4-methyl-;4-METHYLQUINOLINE;4-METHYLCHINOLINE
• CAS NO: 491-35-0
• Molecular Formula: C₁₀H₉N
• Molecular Weight: 143.19
• EINECS: 207-734-2
• Product Categories: Quinoline series;Quinoline Derivertives;Alkylquinolines;Quinolines
• Mol File: 491-35-0.mol
• Article Data: 103

Chemical Properties

• Melting Point: 9-10 °C(lit.)
• Boiling Point: 261-263 °C(lit.)
• Flash Point: >230 °F
• Appearance: /Liquid
• Density: 1.083 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0182mmHg at 25°C
• Refractive Index: n20/D 1.620(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 5.67(at 20℃)
• Water Solubility: Slightly soluble
• Sensitive: Light Sensitive
• Merck: 14,5441
• BRN: 110926
• CAS DataBase Reference: Lepidine(CAS DataBase Reference)
• NIST Chemistry Reference: Lepidine(491-35-0)
• EPA Substance Registry System: Lepidine(491-35-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-68-40
• Safety Statements: 26-36-45-36/37/39-22
• WGK Germany: 3
• RTECS: OH0316000
• F: 8-10
• TSCA: Yes
• Hazardous Substances Data: 491-35-0(Hazardous Substances Data)

Usage

Description

Lepidine, also known as 4-methylquinoline, is an organic compound belonging to the quinoline family. It is characterized by a fused six-membered and five-membered nitrogen-containing ring structure, with a methyl group attached at the 4th position. Lepidine can be synthesized from 4-anilinobutan-2-one in ethanol in the presence of HCl or FeCl3, and its nitration has also been reported.

Uses

Used in Dye Preparation:
Lepidine is utilized in the preparation of certain dyes, contributing to its significance in the chemical industry.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, Lepidine serves as a reagent in the synthesis of azetidine-based ene-amides. These compounds are potent bacterial enoyl ACP reductase inhibitors, which are essential in the development of new antibiotics to combat drug-resistant bacterial infections.
Used in Fluorescent DNA Imaging:
Lepidine is also used as a reagent in the synthesis of cyanine-styryl dyes with enhanced photostability. These dyes are crucial for fluorescent DNA imaging, allowing for better visualization and analysis of DNA structures in various research and diagnostic applications.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 5291, 1987 DOI: 10.1016/S0040-4039(00)96710-8

Purification Methods

Reflux lepidine with BaO, then fractionally distil it. Further purify it via its recrystallised dichromate salt (m 138o) (from H2O). [Cumper et al. J Chem Soc 1176 1962.] [Beilstein 20 III/IV 3477, 20/7 V 389.]

Upstream product

• 118670-86-3 N-(but-3-en-1-yl)-2-iodoaniline 
• 4053-40-1 4-methylquinoline 1-oxide 
• 35982-82-2 quinolin-4-ylmethyl acetate 
• 52562-19-3 2-isopropenylaniline 
• 67-68-5 dimethyl sulfoxide 
• 50-00-0 formaldehyd 
• 103-84-4 Acetanilid 
• 590-90-9 1-Hydroxy-3-butanone 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 
• 142-04-1 aniline hydrochloride 
• 78-94-4 methyl vinyl ketone 
• 75-07-0 acetaldehyde 
• 6220-79-7 4-phenylamino-butan-2-one 

Downstream Products

• 58246-00-7 2-acetyl-1,2-dihydroisoquinoline-1-acetic acid 
• 79332-27-7 2-acetyl-1-(4-quinolylmethyl)-1,2-dihydroisoquinoline 
• 55908-35-5 2--ethanol-(1) 
• 152121-37-4 1-(4-fluoro-phenyl)-2-quinolin-4-yl-ethane-1,2-dione 2-oxime 
• 66471-26-9 1-benzyl-4-methylquinolin-1-ium bromide 
• 583854-88-0 2-({4-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-1-ethenyl]-1-quinoliniumyl}methyl)-1-benzenesulfonate 
• 583854-89-1 4-({4-[(E)-2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-1-ethenyl]-1-quinoliniumyl}methyl)-1-benzenesulfonate 
• 152121-36-3 1-(4-fluoro-phenyl)-2-quinolin-4-yl-ethanone 
• 878801-85-5 4-[(E)-2-(3,4-dimethoxyphenyl)ethen-1-yl]quinoline 
• 32863-56-2 1-butyl-4-methylquinolin -1-ium iodide 

Relevant articles and documents

A novel approach to vapor-phase synthesis of 2- and 4-methylquinoline from lactic acid and aniline

A novel and green route for vapor-phase synthesis of 2- and 4-methylquinoline was provided in this work, in which lactic acid as one of the reactants was for the first time employed. Various influencing factors, including types of catalysts, reaction temperature and stability of catalyst were investigated systematically. The results showed that a 67.6% total yield of quinolines was obtained over the HBeta catalyst. The characterization by using BET, NH3-TPD and pyridine-IR techniques revealed that strong Br?nsted acid sites are favorable for generation of 2- and 4-methylquinoline whereas Lewis acid sites could increase the proportion of 4-methylquinoline in target products. Besides, a feasible reaction pathway to synthesize 2- and 4-methylquinoline was proposed on the basis of the reaction products.

-

-

Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents

Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).

Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes

We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.

Copper-mediated formal [5+1] annulation of 2-vinylanilines and glyoxylic acid: A facile approach for the synthesis of 4-arylated quinolines

A copper-mediated formal [5 + 1] oxidative annulation of 2-vinylanilines and glyoxylic acid to 4-arylated quinolines was developed. A series of 4-arylated quinoline derivatives were obtained in good to excellent yields. This protocol could be carried out efficiently on gram scale. The transformation probably underwent nucleophilic addition/6π electrocyclization/oxidative aromatization and the elimination of CO2 cascade processes.