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

• 64-17-5 ethanol 
• 6975-85-5 1-methoxybutan-3-one 
• 142-04-1 aniline hydrochloride 
• 75-07-0 acetaldehyde 
• 62-53-3 aniline 
• 590-90-9 1-Hydroxy-3-butanone 
• 98-95-3 nitrobenzene 
• 74-86-2 acetylene 
• 109-87-5 Dimethoxymethane 
• 67-64-1 acetone 
• 123-63-7 paracetaldehyde 
• 64-19-7 acetic acid 
• 14528-46-2 (8Ξ)-cinchon-8-ene 
• 36069-28-0 10,11-Dihydro-cinchonan 

Downstream Products

• 58246-00-7 2-acetyl-1,2-dihydroisoquinoline-1-acetic acid 
• 79332-27-7 2-acetyl-1-(4-quinolylmethyl)-1,2-dihydroisoquinoline 
• 21233-61-4 quinoline-4-carboxylic acid methyl ester 
• 37864-30-5 (4-methylquinolin-2-yl)(phenyl)methanone 
• 100-52-7 benzaldehyde 
• 134-81-6 benzil 
• 65-85-0 benzoic acid 
• 4053-40-1 4-methylquinoline 1-oxide 
• 768-95-6 1-adamanthanol 
• 77492-66-1 4-methyl-2-(tricyclo[3.3.1.1^3,7]dec-1-yl)quinolone 
• 97691-25-3 2-tert-butyl-4-methylquinoline 
• 4363-93-3 quinoline-4-carboxaldehyde 
• 486-74-8 4-quinolinic acid 
• 137634-62-9 4-methyl-2-phenethylquinoline 

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.

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Method for realizing oxidative dehydrogenation of nitrogen-containing heterocyclic ring by using biomass-based carbon material

The invention provides a method for realizing oxidative dehydrogenation of a nitrogen-containing heterocyclic ring by using a biomass-based carbon material, and belongs to the field of organic synthesis. According to the method, the raw materials of the biomass-based carbon material comprise wheat, sorghum, rice, corn straw, wheat straw, peanut shells, sesame shells, bean shells and the like, and are crushed and then ground into powder, the powder is fully mixed with an inorganic alkali, and calcination is performed in an inert gas atmosphere to prepare the biomass-based carbon material; and by using air as an oxygen source, at a temperature of 50-120 DEG C, oxidative dehydrogenation of nitrogen-containing heterocyclic compounds to synthesize quinoline compounds, isoquinoline compounds, acridine compounds, quinazoline compounds, indole compounds, imine compounds, and even quinoline compounds with pharmaceutical activity can be achieved. According to the present invention, easily available wheat flour is adopted as a raw material to prepare a non-metal catalyst, the alkali is not added during the reaction process, and a remarkable industrial application prospect is achieved.

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis

We report the design of a bifunctional metal–organic layer (MOL), Hf12-Ru-Co, composed of [Ru(DBB)(bpy)2]2+ [DBB-Ru, DBB=4,4′-di(4-benzoato)-2,2′-bipyridine; bpy=2,2′-bipyridine] connecting ligand as a photosensitizer and Co(dmgH)2(PPA)Cl (PPA-Co, dmgH=dimethylglyoxime; PPA=4-pyridinepropionic acid) on the Hf12 secondary building unit (SBU) as a hydrogen-transfer catalyst. Hf12-Ru-Co efficiently catalyzed acceptorless dehydrogenation of indolines and tetrahydroquinolines to afford indoles and quinolones. We extended this strategy to prepare Hf12-Ru-Co-OTf MOL with a [Ru(DBB)(bpy)2]2+ photosensitizer and Hf12 SBU capped with triflate as strong Lewis acids and PPA-Co as a hydrogen transfer catalyst. With three synergistic active sites, Hf12-Ru-Co-OTf competently catalyzed dehydrogenative tandem transformations of indolines with alkenes or aldehydes to afford 3-alkylindoles and bisindolylmethanes with turnover numbers of up to 500 and 460, respectively, illustrating the potential use of MOLs in constructing novel multifunctional heterogeneous catalysts.