2585-18-4

Basic information

• Product Name: 4,7-dimethylcarbostyril
• Synonyms: 4,7-dimethyl-1H-quinolin-2-one;4,7-dimethylcarbostyril
• CAS NO: 2585-18-4
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.21114
• Mol File: 2585-18-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 350.1°C at 760 mmHg
• Flash Point: 206°C
• Appearance: /
• Density: 1.107g/cm³
• Vapor Pressure: 4.5E-05mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: 4,7-dimethylcarbostyril(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7-dimethylcarbostyril(2585-18-4)
• EPA Substance Registry System: 4,7-dimethylcarbostyril(2585-18-4)

Safety Data

• Hazardous Substances Data: 2585-18-4(Hazardous Substances Data)

Usage

Description

4,7-Dimethylcarbostyril, also known as 4,7-dimethylquinolin-2(1H)-one, is an organic compound with a quinoline-based structure featuring two methyl groups at the 4th and 7th positions. It is characterized by its potential applications in various fields due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
4,7-Dimethylcarbostyril is used as a reagent for the preparation of citralidene hydrazido quinolinones, which possess antibacterial activity. This application is significant in the development of new drugs to combat bacterial infections, particularly in the context of increasing antibiotic resistance.
Used in Chemical Synthesis:
In addition to its pharmaceutical applications, 4,7-dimethylcarbostyril can be utilized as an intermediate in the synthesis of various organic compounds, contributing to the development of novel chemical products with diverse applications across different industries.

InChI:InChI=1/C11H11NO/c1-7-3-4-9-8(2)6-11(13)12-10(9)5-7/h3-6H,1-2H3,(H,12,13)

Upstream product

• 25233-46-9 3-oxo-N-m-tolylbutanamide 
• 108-44-1 1-amino-3-methylbenzene 
• 53078-85-6 2-bromo-5-methylaniline 
• 141-97-9 ethyl acetoacetate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 124-38-9 carbon dioxide 

Downstream Products

• 40941-54-6 4,7-dimethylquinoline 
• 53761-46-9 1,4,7-trimethyl-1H-quinolin-2-one 
• 88499-92-7 2-chloro-4,7-dimethylquinoline 
• 161095-64-3 4,7-dimethyl-1-<(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl>-1,2-dihydroquinolin-2-one 

Relevant articles and documents

Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.

Synthesis and antileishmanial evaluation of thiazole orange analogs

Cyanine compounds have previously shown excellent in vitro and promising in vivo antileishmanial efficacy, but the potential toxicity of these agents is a concern. A series of 22 analogs of thiazole orange ((Z)-1-methyl-4-((3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)quinolin-1-ium salt), a commercial cyanine dye with antileishmanial activity, were synthesized in an effort to increase the selectivity of such compounds while maintaining efficacy. Cyanines possessing substitutions on the quinolinium ring system displayed potency against Leishmania donovani axenic amastigotes that differed little from the parent compound (IC50 12–42 nM), while ring disjunction analogs were both less potent and less toxic. Changes in DNA melting temperature were modest when synthetic oligonucleotides were incubated with selected analogs (ΔTm ≤ 5 °C), with ring disjunction analogs showing the least effect on this parameter. Despite the high antileishmanial potency of the target compounds, their toxicity and relatively flat SAR suggests that further information regarding the target(s) of these molecules is needed to aid their development as antileishmanials.

Lactamization of sp2C?H Bonds with CO2: Transition-Metal-Free and Redox-Neutral

The first direct use of carbon dioxide in the lactamization of alkenyl and heteroaryl C?H bonds to synthesize important 2-quinolinones and polyheterocycles in moderate to excellent yields is reported. Carbon dioxide, a nontoxic, inexpensive, and readily available greenhouse gas, acts as an ideal carbonyl source. Importantly, this transition-metal-free and redox-neutral process is eco-friendly and desirable for the pharmaceutical industry. Moreover, these reactions feature a broad substrate scope, good functional group tolerance, facile scalability, and easy product derivatization.