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

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

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.

Partial hydrogenation of substituted pyridines and quinolines: A crucial role of the reaction conditions

Hydrogenation of pyridyl and quinolyl compounds 2-substituted with a carbonyl group (1a-c and 2b,c) using PtO2 and 1 equiv. of HCl (conditions A) provides clean and total formation of the desired amino alcohol (hydrogenation of the heterocyclic ring and of the carbonyl) while under conditions B1 and/or B2 (concentrated HCl or pure CF 3CO2H) the heterocyclic ring remains untouched and other aromatic parts are hydrogenated providing complex mixtures. When the heterocyclic ring is substituted by an alkyl group (quinaldine 3) conditions A provide mixtures while under conditions B2 (pure CF 3CO2H) the benzene ring is cleanly hydrogenated leading to a pure product.