605-88-9

Usage

Uses

Used in Environmental Monitoring and Research:
2-Methylbenzo[h]quinoline is utilized as a biomarker for environmental pollution, particularly in studies related to cigarette smoke and combustion emissions. Its presence helps in assessing the level of exposure to toxic substances and the potential health risks associated with them.
Used in Toxicology and Carcinogenesis Studies:
As a suspected human carcinogen, 2-methylbenzo[h]quinoline serves as a model compound in toxicology and carcinogenesis research. It is used to investigate the mechanisms of DNA damage, mutagenicity, and carcinogenicity, contributing to the development of preventive measures and therapeutic strategies against related health issues.
Used in Chemical Education and Training:
2-Methylbenzo[h]quinoline can be employed as a teaching aid in chemical education and training programs. It provides an opportunity for students and professionals to understand the properties, hazards, and environmental implications of polycyclic aromatic hydrocarbons, enhancing their knowledge and skills in chemical safety and risk management.
Used in Regulatory Compliance and Policy Development:
The identification of 2-methylbenzo[h]quinoline as a toxic substance and environmental pollutant plays a crucial role in regulatory compliance and policy development. It informs the establishment of safety standards, guidelines, and regulations to control its emission, exposure, and disposal, thereby protecting public health and the environment.

InChI:InChI=1/C14H11N/c1-10-6-7-12-9-8-11-4-2-3-5-13(11)14(12)15-10/h2-9H,1H3

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 134-32-7 1-amino-naphthalene 
• 230-27-3 7,8-benzoquinoline 
• 917-54-4 methyllithium 
• 64-17-5 ethanol 
• 74-86-2 acetylene 
• 201230-82-2 carbon monoxide 
• 91-59-8 naphthalen-2-ylamine 
• 815-68-9 3-acetylpentane-2,4-dione 
• 176853-41-1 1-amino naphthalene-2-carboxaldehyde 
• 1004545-92-9 1-(1-aminonaphthalen-2-yl)but-3-en-1-ol 
• 123-73-9 crotonaldehyde 
• 109-92-2 ethyl vinyl ether 
• 17104-70-0 benzo[h]quinoline 1-oxide 

Downstream Products

• 904886-12-0 2-formylbenzo[h]quinoline 
• 224564-90-3 (2-methyl-7,8-benzoquinolinato)hydrido(aqua)bis(triphenylphosphine)iridium(III) tetrafluoroborate 
• 1318193-44-0 N-(2-(benzo[h]quinolin-2-yl)-1-phenylethyl)-4-methylbenzenesulfonamide 
• 1446451-55-3 2,2'-(2-phenylpropane-1,3-diyl)bis(benzo[h]quinoline) 

Relevant academic research and scientific papers

Rhodium-Catalyzed C-H Annulation of Free Anilines with Vinylene Carbonate as a Bifunctional Synthon

Chemical transformation with vinylene carbonate as an emerging synthetic unit has recently attracted considerable attention. This report is a novel conversion pattern with vinylene carbonate, in which such a vibrant reagent unprecedentedly acts as a difunctional coupling partner to complete the C-H annulation of free anilines. From commercially available substrates, this protocol leads to the rapid construction of synthetically versatile 2-methylquinoline derivatives (43 examples) with excellent functionality tolerance.

Bifunctional thiophosphinamide catalyzed highly enantioselective Michael addition of acetone to (E)-2-azido β-nitrostyrenes and the subsequent reductive cyclization

We have proven that primary amine/thiophosphinamide incorporating (1R,2R)-1,2-diphenylethane-1,2-diamine is an efficient catalyst for the asymmetric Michael addition of acetone to (E)-2-azido β-nitrostyrenes. Under the optimal reaction conditions, the corresponding Michael addition products were obtained in excellent yields with almost perfect stereocontrol. Upon treatment with Et3SiH/InCl3, the Michael addition products could be successfully converted to the related 2-methyltetrahydroquinolines in acceptable yields with moderate to excellent diastereoselectivity and without appreciable loss in optical purity. This process provides a highly enantioselective pathway for the synthesis of biologically important 2-methyltetrahydroquinoline derivatives.

Synthesis of benzoquinoline derivatives from formyl naphthylamines via Friedl?nder annulation under metal-free conditions

Abstract: The synthesis of benzoquinolines and benzoquinolinones via Friedl?nder-type condensation of aminonaphthalene carbaldehydes with (1) primary or secondary alcohols mediated by urea/KOH or with (2) diketones or β-ketoesters is described. The behavi

Metallaphotoredox-Mediated Csp2-H Hydroxylation of Arenes under Aerobic Conditions

The direct hydroxylation of 2-arylpyridines and 2-arylbenzothiazoles via the merger of organic photoredox and metal catalysis is reported where 4CzIPN is used as the visible-light photocatalyst and Pd(OAc)2 as the metal catalyst. This method has been employed to synthesize organic molecules exhibiting excited-state intramolecular proton transfer properties for generating tunable luminescence responses.

Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines

An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.

Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines

A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino synthesis of quinolines from anilines.

Transition-Metal-Free Regioselective Alkylation of Pyridine N-Oxides Using 1,1-Diborylalkanes as Alkylating Reagents

Reported herein is an unprecedented base-promoted deborylative alkylation of pyridine N-oxides using 1,1-diborylalkanes as alkyl sources. The reaction proceeds efficiently for a wide range of pyridine N-oxides and 1,1-diborylalkanes with excellent regioselectivity. The utility of the developed method is demonstrated by the sequential C?H arylation and methylation of pyridine N-oxides. The reaction also can be applied for the direct introduction of a methyl group to 9-O-methylquinine N-oxide, thus it can serve as a powerful method for late-stage functionalization.

Discovery and efficient synthesis of a biologically active alkaloid inspired by thiostrepton biosynthesis

Thiostrepton, a natural peptide macrocycle, is of great interest due to its structural complexity and numerous biological activities, including anti-bacterial, anti-tumor, and anti-plasmodial activities. The quinaldic acid (QA) moiety-containing side ring (loop 2) was proven to play an important role in carrying out these functions. Previously, we proposed biosynthetic logic for thiostrepton loop 2 and demonstrated the formation mechanism of QA. Herein, we report the discovery and efficient synthesis of a biologically active alkaloid, that is, a key intermediate involved in the thiostrepton biosynthetic pathway. A chemo-enzymatic method was performed to synthesize the molecule, and a series of analogs were prepared for bioassays, which included the examination of anti-bacterial and anti-tumor activities.

A facile synthesis of substituted 2-alkylquinolines through [3 + 3] annulation between 3-ethoxycyclobutanones and aromatic amines at room temperature

An efficient single-step approach toward the synthesis of 2-alkylquinolines is described. Through a Lewis acid mediated [3 + 3] annulation reaction between 3-ethoxycyclobutanones and aromatic amines, a variety of multisubstituted 2-alkylquinoline derivatives were prepared regioselectively at room temperature.

Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation

Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright