27104-55-8

Basic information

• Product Name: phenyl(quinolin-2-yl)methanol
• CAS NO: 27104-55-8
• Molecular Formula: C₁₆H₁₃NO
• Molecular Weight: 235.2805
• Mol File: 27104-55-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 410.8°C at 760 mmHg
• Flash Point: 202.2°C
• Density: 1.21g/cm³
• Vapor Pressure: 1.74E-07mmHg at 25°C
• Refractive Index: 1.674
• CAS DataBase Reference: phenyl(quinolin-2-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl(quinolin-2-yl)methanol(27104-55-8)
• EPA Substance Registry System: phenyl(quinolin-2-yl)methanol(27104-55-8)

Safety Data

• Hazardous Substances Data: 27104-55-8(Hazardous Substances Data)

Upstream product

• 5470-96-2 quinoline 2-carbaldehyde 
• 93-10-7 quinoline-2-carboxylic acid 
• 100-52-7 benzaldehyde 
• 67-56-1 methanol 
• 16576-25-3 2-benzoylquinoline 
• 91-22-5 quinoline 
• 612-62-4 2-Chloroquinoline 
• 98-86-2 acetophenone 
• 2005-43-8 2-bromoquinoline 
• 91-63-4 2-methylquinoline 
• 1613-37-2 Quinoline N-oxide 
• 52670-38-9 2-ethynylaniline 
• 1074-12-0 phenylglyoxal hydrate 

Downstream Products

• 1745-77-3 2-benzylquinoline 
• 1513327-00-8 2-(1-phenylethyl)quinoline 
• 132499-94-6 NPHQTS 
• 16576-25-3 2-benzoylquinoline 
• 70391-44-5 2-[(2-morpholin-4-yl-ethoxy)-phenyl-methyl]-quinoline 

Relevant articles and documents

Copper(i)-catalyzed tandem synthesis of 2-acylquinolines from 2-ethynylanilines and glyoxals

An efficient one-step synthesis of 2-acylquinolines using a copper-catalyzed tandem reaction of 2-ethynylanilines with glyoxals in the presence of piperidine has been developed. This new protocol successfully avoids multi-step operation and the use of highly toxic cyanides required in traditional methods, and provides a practical tool for synthetic and pharmaceutical chemists. Various 2-acylquinolines are obtained with perfect regioselectivity in moderate to good yields (up to 86%). The potential synthetic utility of this method is exemplified by a large-scale experiment and synthetic transformation of the products.

Photochemical C?H Hydroxyalkylation of Quinolines and Isoquinolines

We report herein a visible light-mediated C?H hydroxyalkylation of quinolines and isoquinolines that proceeds via a radical path. The process exploits the excited-state reactivity of 4-acyl-1,4-dihydropyridines, which can readily generate acyl radicals upon blue light absorption. By avoiding the need for external oxidants, this radical-generating strategy enables a departure from the classical, oxidative Minisci-type pattern and unlocks a unique reactivity, leading to hydroxyalkylated heteroarenes. Mechanistic investigations provide evidence that a radical-mediated spin-center shift is the key step of the process. The method's mild reaction conditions and high functional group tolerance accounted for the late-stage functionalization of active pharmaceutical ingredients and natural products.

Tributylmagnesium ate complex-mediated bromine-magnesium exchange of bromoquinolines: A convenient access to functionalized quinolines

2-, 3- and 4-bromoquinolines were converted to the corresponding lithium tri(quinolyl)magnesates at -10°C by treatment with Bu3MgLi in THF or toluene. The resulting organomagnesium derivatives were quenched by various electrophiles to afford functionalized quinolines.