611-32-5 Usage
Description
8-Methylquinoline is an organic compound belonging to the quinoline family, characterized by the presence of a methyl group at the 8th position on the quinoline ring. It exhibits unique chemical properties and has been the subject of various studies for its potential applications in different fields.
Uses
Used in Chemical Synthesis:
8-Methylquinoline is used as a key intermediate in the preparation of osmium chloridophosphine complexes, which are valuable catalysts in various chemical reactions. Its presence in these complexes enhances their catalytic activity and selectivity.
Used in Pharmaceutical Research:
8-Methylquinoline serves as a quinoline carbene tautomer, which is a significant class of compounds with potential pharmaceutical applications. These tautomers have been studied for their biological activities, including their ability to inhibit certain enzymes and their potential as antimalarial agents.
Used in Toxicology Studies:
The tumorigenic potential of 8-methylquinoline has been evaluated in newborn CD-1 mice and Sprague-Dawley rats, providing valuable insights into its safety and potential risks for human exposure. These studies contribute to the understanding of the compound's toxicological profile.
Used in Computational Chemistry:
8-Methylquinoline is utilized in the quantitative structure-activity relationship (QSAR) treatment of mutagenicity and cytotoxicity of quinolines. This application aids in predicting the biological effects of related compounds and designing safer and more effective drugs.
Synthesis Reference(s)
The Journal of Organic Chemistry, 45, p. 1514, 1980 DOI: 10.1021/jo01296a035
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
8-Methylquinoline may be sensitive to exposure to light. May react vigorously with strong oxidizing agents and strong acids . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Fire Hazard
8-Methylquinoline is combustible.
Purification Methods
Purify it as for 2-methylquinoline. The phosphate and picrate have m 158o and m 201o, respectively. [Beilstein 20 III/IV 3500, 20/7 V 405.]
Check Digit Verification of cas no
The CAS Registry Mumber 611-32-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 1 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 611-32:
(5*6)+(4*1)+(3*1)+(2*3)+(1*2)=45
45 % 10 = 5
So 611-32-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H9N/c1-8-4-2-5-9-6-3-7-11-10(8)9/h2-7H,1H3
611-32-5Relevant articles and documents
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Novgorodova et al.
, (1973)
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Metal–Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis
Quan, Yangjian,Lan, Guangxu,Shi, Wenjie,Xu, Ziwan,Fan, Yingjie,You, Eric,Jiang, Xiaomin,Wang, Cheng,Lin, Wenbin
supporting information, p. 3115 - 3120 (2020/12/09)
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.
Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of N-Heterocycles
Manna, Srimanta,Kong, Wei-Jun,B?ckvall, Jan-E.
supporting information, p. 13725 - 13729 (2021/09/08)
Herein, an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions is described. The dehydrogenation process, involving several electron-transfer steps, is inspired by oxidations occurring in the respiratory chain. An environmentally friendly and inexpensive iron catalyst together with a hydroquinone/cobalt Schiff base hybrid catalyst as electron-transfer mediator were used for the substrate-selective dehydrogenation reaction of various N-heterocycles. The method shows a broad substrate scope and delivers important heterocycles in good-to-excellent yields.
