16032-35-2

Basic information

• Product Name: 8-Quinolinemethanol
• Synonyms: 8-Quinolinemethanol;quinolin-8-ylmethanol(SALTDATA: FREE);8-Quinolinylmethanol;8-quinolylmethanol
• CAS NO: 16032-35-2
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.19
• Mol File: 16032-35-2.mol

Chemical Properties

• Melting Point: 75-76℃
• Boiling Point: 334.8 °C at 760 mmHg
• Flash Point: 156.3 °C
• Appearance: /
• Density: 1.218
• PKA: 13.80±0.10(Predicted)
• CAS DataBase Reference: 8-Quinolinemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Quinolinemethanol(16032-35-2)
• EPA Substance Registry System: 8-Quinolinemethanol(16032-35-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 16032-35-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
8-Quinolinemethanol is used as an antimicrobial agent for its antiparasitic, antiviral, antibacterial, antifungal, and anticancer activities. It is particularly effective in treating various infections and diseases caused by microorganisms.
Used in Chemical Research:
8-Quinolinemethanol is used as a research compound for studying its antimicrobial properties and potential applications in the development of new drugs and therapies. Its broad-spectrum activity makes it a valuable tool in the search for novel treatments and interventions.
Used in Anticancer Applications:
8-Quinolinemethanol is used as an anticancer agent, targeting various types of cancer cells and potentially enhancing the efficacy of conventional chemotherapy. Its antimicrobial properties may also contribute to its anticancer activity by disrupting the microenvironment of tumors.
Used in Drug Delivery Systems:
8-Quinolinemethanol can be incorporated into drug delivery systems to improve the delivery, bioavailability, and therapeutic outcomes of antimicrobial and anticancer treatments. Its chemical properties may allow for the development of novel carriers and formulations that enhance its effectiveness and reduce side effects.
Safety Note:
It is important to handle 8-Quinolinemethanol with care, as it may cause irritation to the eyes, skin, and mucous membranes if improperly handled. Proper safety measures should be taken to minimize the risk of exposure and ensure the safe use of 8-Quinolinemethanol in various applications.

InChI:InChI=1S/C10H9NO/c12-7-9-4-1-3-8-5-2-6-11-10(8)9/h1-6,12H,7H2

Upstream product

• 38707-70-9 8-formylquinoline 
• 15402-71-8 8-(aminomethyl)quinoline 
• 7496-46-0 8-bromomethyl-quinoline 
• 25635-22-7 quinoline-8-carboxylic acid ethylester 
• 79663-29-9 (quinolin-8-yl)methyl acetate 
• 611-32-5 8-methylquinoline 
• 91-22-5 quinoline 
• 52601-70-4 8-methyl-1,2,3,4-tetrahydroquinoline 
• 80937-33-3 oxygen 
• 64-19-7 acetic acid 
• 1451194-15-2 C₁₈H₁₄N₂O₄Pd 
• 1451194-14-1 C₁₇H₁₃N₂O₅PdS^(1-)*Li⁽¹⁺⁾ 
• 1063398-52-6 C₂₁H₂₁N₂O₄Pd 
• 77934-77-1 quinolin-8-ylmethyl 2-methylbenzoate 

Downstream Products

• 112646-08-9 (1-Benzyl-1,2,3,4-tetrahydro-quinolin-8-yl)-methanol 
• 112644-23-2 8-(1H-Benzoimidazole-2-sulfinylmethyl)-1-ethyl-1,2,3,4-tetrahydro-quinoline 
• 112643-72-8 1-Benzyl-8-(5-methyl-1H-benzoimidazol-2-ylsulfanylmethyl)-1,2,3,4-tetrahydro-quinoline 
• 112644-50-5 1-Benzyl-8-(5-methyl-1H-benzoimidazole-2-sulfinylmethyl)-1,2,3,4-tetrahydro-quinoline 

Relevant articles and documents

Aerobic C-H acetoxylation of 8-methylquinoline in PdII- pyridinecarboxylic acid systems: Some structure-reactivity relationships

Catalytic oxidative C-H acetoxylation of 8-methylquinoline as a model substrate with O2 as oxidant was performed using palladium(II) carboxylate catalysts derived from four different pyridinecarboxylic acids able to form palladium(II) chelates of different size. A comparison of the rates of the substrate C-H activation and the O2 activation steps shows that the C-H activation step is rate-limiting, whereas the O2 activation occurs at a much faster rate already at 20 C. The chelate ring size and the chelate ring strain of the catalytically active species are proposed to be the key factors affecting the rate of the C-H activation.

Monodisperse CuPd alloy nanoparticles supported on reduced graphene oxide as efficient catalyst for directed C?H activation

The palladium-catalyzed selective activation of C–H bonds is of great importance for the construction of diverse bioactive molecules. Herein, monodisperse CuPd alloy nanoparticles supported on reduced graphene oxide have been used as high efficient and re

Multi-Functional Oxidase Activity of CYP102A1 (P450BM3) in the Oxidation of Quinolines and Tetrahydroquinolines

Tetrahydroquinoline, quinoline, and dihydroquinolinone are common core motifs in drug molecules. Screening of a 48-variant library of the cytochrome P450 enzyme CYP102A1 (P450BM3), followed by targeted mutagenesis based on mutation-selectivity correlations from initial hits, has enabled the hydroxylation of substituted tetrahydroquinolines, quinolines, and 3,4-dihydro-2-quinolinones at most positions around the two rings in good to high yields at synthetically relevant scales (1.5 g L?1 day?1). Other oxidase activities, such as C?C bond desaturation, aromatization, and C?C bond formation, were also observed. The enzyme variants, with mutations at the key active site residues S72, A82, F87, I263, E267, A328, and A330, provide direct and sustainable routes to oxy-functionalized derivatives of these building block molecules for synthesis and drug discovery.

Palladium-Catalyzed C-H Bond Functionalization Reactions Using Phosphate/Sulfonate Hypervalent Iodine Reagents

A new and operationally simple approach for palladium-catalyzed C-H functionalization reactions utilizing an organophosphorus/sulfonate hypervalent iodine reagent as both an oxidant and the source of a functional group has been developed. Through this method, the oxidative phosphorylation-, sulfonation-, and hydroxylation of unactivated benzyl C(sp3)-H bonds, along with the hydroxylation and arylation of aryl C(sp2)-H bonds, are successfully realized under mild conditions and with excellent site-selectivity. The versatile C-OSO2R bond provides a platform for a wide array of subsequent diversification reactions.

Catalytic C(sp3)?H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ

Herein, we report the palladium-catalyzed direct arylation of unactivated aliphatic C?H bonds in free primary amines. This method takes advantage of an exo-imine-type directing group (DG) that can be generated and removed in situ. A range of unprotected aliphatic amines are suitable substrates, undergoing site-selective arylation at the γ-position. Methyl as well as cyclic and acyclic methylene groups can be activated. Furthermore, when aniline-derived substrates were used, preliminary success with δ-C?H arylation was achieved. The feasibility of using the DG component in a catalytic fashion was also demonstrated.

Synthesis and anti-norovirus activity of pyranobenzopyrone compounds

During the last decade, noroviruses have gained media attention as the cause of large scale outbreaks of gastroenteritis on cruise ships, dormitories, nursing homes, etc. Although noroviruses do not multiply in food or water, they can cause large outbreaks because approximately 10-100 virions are sufficient to cause illness in a healthy adult. Recently, it was shown that the activity of acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT1) enzyme may be important in norovirus infection. In search of anti-noroviral agents based on the inhibition of ACAT1, we synthesized and evaluated the inhibitory activities of a class of pyranobenzopyrone molecules containing amino, pyridine, substituted quinolines, or 7,8-benzoquinoline nucleus. Three of the sixteen evaluated compounds possess ED50 values in the low micrometer range. 2-Quinolylmethyl derivative 3A and 4-quinolylmethyl derivative 4A showed ED50 values of 3.4 and 2.4 μM and TD50 values of >200 and 96.4 μM, respectively. The identified active compounds are suitable for further modification for the development of anti-norovirus agents.

Catalytic aerobic oxidation of substituted 8-methylquinolines in Pd II-2,6-pyridinedicarboxylic acid systems

The ability of PdII complexes derived from 2,6- pyridinedicarboxylic acids to catalyze homogeneous regioselective aerobic oxidation of 5- and 6-substituted 8-methylquinolines in AcOH-Ac2O solution to produce corresponding 8-quinolylm

2,4-DIAMINOQUINAZOLINES FOR SPINAL MUSCULAR ATROPHY

2,4-Diaminoquinazolines of formulae I-IV and VI (I, II, III, IV and VI) are useful for treating spinal muscular atrophy (SMA).

Quinoline derivatives and medicinal use thereof

A quinoline derivative represented by the following formula (1): allows PPARα or γ which is an intranuclear transcription factor, to function strongly and is low in toxicity. By using this compound as an active ingredient, there can be provided a preventive or therapeutic agent for various diseases related to PPARα or γ.