58960-02-4

Basic information

• Product Name: 5-Methyl-1,2,3,4-tetrahydroquinoline
• Synonyms: 5-Methyl-1,2,3,4-tetrahydroquinoline
• CAS NO: 58960-02-4
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.21692
• Mol File: 58960-02-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Methyl-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-1,2,3,4-tetrahydroquinoline(58960-02-4)
• EPA Substance Registry System: 5-Methyl-1,2,3,4-tetrahydroquinoline(58960-02-4)

Safety Data

• Hazardous Substances Data: 58960-02-4(Hazardous Substances Data)

Upstream product

• 95-81-8 2-chloro-5-methylaniline 
• 20151-46-6 5-methyl-1,2,3,4-tetrahydroquinolin-2-one 
• 7661-55-4 5-methylquinoline 
• 56961-81-0 8-chloro-5-methylquinoline 
• 64-17-5 ethanol 
• 153749-71-4 2,4-dichloro-5-methyl quinoline 

Downstream Products

• 7661-55-4 5-methylquinoline 

Relevant articles and documents

Cu-Catalyzed Chemoselective Reduction of N-Heteroaromatics with NH3·BH3 in Aqueous Solution

An efficient catalytic system was successfully developed on reduction of N-heteroaromatics with H3N?BH3 as hydrogen source in CuSO4 solution, featuring excellent chemoselectivity as well as very broad functional group tolerance. Various challenging substrates, such as OH-, NH2-, Cl-, Br-, etc., contained quinolines, quinoxalines, 1,5-naphthyridines and quinazolines were all reduced smoothly. Mechanistic studies suggested that [Cu-H] intermediate might be generated from NH3?BH3, which was believed to form with H3N?BH3 in CuSO4 solution.

Discovery of tetrahydroquinolines and benzomorpholines as novel potent RORγt agonists

The retinoic acid receptor-related orphan receptor γt (RORγt) is an important nuclear receptor that regulates the differentiation of Th17 cells and production of interleukin 17(IL-17). RORγt agonists increase basal activity of RORγt and could provide a potential approach to cancer immunotherapy. Herein, hit compound 1 was identified as a weak RORγt agonist during in-house library screening. Changes in LHS core of 1 led to the identification of tetrahydroquinoline compound 6 as a partial RORγt agonist (max. act. = 39.3%). Detailed structure-activity relationship on substituent of the LHS core, amide linker and RHS arylsulfonyl moiety was explored and a novel series of tetrahydroquinolines and benzomorpholines was discovered as potent RORγt agonists. Tetrahydroquinoline compound 8g (EC50 = 8.9 ± 0.4 nM, max. act. = 104.5%) and benzomorpholine compound 9g (EC50 = 7.5 ± 0.6 nM, max. act. = 105.8%) were representative compounds with high RORγt agonistic activity in dual FRET assay, and they showed good activity in cell-based Gal4 reporter gene assay and Th17 cell differentiation assay (104.5% activation at 300 nM of 8g; 59.4% activation at 300 nM of 9g). The binding modes of 8g and 9g as well as the two RORγt inverse agonists accidentally discovered were also discussed.

Simple manganese carbonyl catalyzed hydrogenation of quinolines and imines

Manganese-catalyzed hydrogenation of unsaturated molecules has made tremendous progresses recently benefiting from non-innocent pincer or bidentate ligands for manganese. Herein, we describe the hydrogenation of quinolines and imines catalyzed by simple manganese carbonyls, Mn2(CO)10 or MnBr(CO)5, thus eliminating the prerequisite pincer-type or bidentate ligands.