1745-77-3

Basic information

• Product Name: 2-BENZYLQUINOLINE
• Synonyms: 2-BENZYLQUINOLINE
• CAS NO: 1745-77-3
• Molecular Formula: C₁₆H₁₃N
• Molecular Weight: 219.28
• Mol File: 1745-77-3.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 352.5°Cat760mmHg
• Flash Point: 151.3°C
• Appearance: /
• Density: 1.117g/cm³
• Vapor Pressure: 7.79E-05mmHg at 25°C
• Refractive Index: 1.649
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-BENZYLQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BENZYLQUINOLINE(1745-77-3)
• EPA Substance Registry System: 2-BENZYLQUINOLINE(1745-77-3)

Safety Data

• Hazardous Substances Data: 1745-77-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-BENZYLQUINOLINE is used as a building block for the synthesis of pharmaceuticals due to its versatile chemical properties, contributing to the development of new drugs with potential therapeutic applications.
Used in Pesticide Industry:
In the pesticide industry, 2-BENZYLQUINOLINE is utilized as a key component in the creation of various pesticides, leveraging its chemical structure to combat pests and protect crops.
Used in Dye Industry:
2-BENZYLQUINOLINE serves as a precursor in the synthesis of dyes, providing a foundation for the production of colorants used in various applications, including textiles and printing.
Used in Research and Development:
2-BENZYLQUINOLINE is used as a research compound for exploring its potential therapeutic properties, such as its activity as an anti-tumor agent, which could lead to the development of new cancer treatments.
Used in Microbiology:
2-BENZYLQUINOLINE is employed as an antimicrobial agent, inhibiting the growth of harmful microorganisms, and has potential applications in the development of new antibiotics or antifungal agents.

InChI:InChI=1/C16H13N/c1-2-6-13(7-3-1)12-15-11-10-14-8-4-5-9-16(14)17-15/h1-11H,12H2

Upstream product

• 694-59-7 pyridine N-oxide 
• 1613-37-2 Quinoline N-oxide 
• 103-82-2 phenylacetic acid 
• 122-78-1 phenylacetaldehyde 
• 27104-55-8 α-phenyl-2-quinolinemethanol 
• 5470-96-2 quinoline 2-carbaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 7664-41-7 ammonia 
• 108-90-7 chlorobenzene 
• 116249-83-3 benzyl 2-quinolyl sulfoxide 
• 88062-13-9 2-benzyl 3,4-dihydro quinoline 
• 122080-53-9 phenyl 2-quinolyl sulfoxide 
• 6921-34-2 benzylmagnesium chloride 
• 23974-78-9 2-benzylquinoline 1-oxide 

Downstream Products

• 1139921-59-7 (R)-2-benzyl-1,2,3,4-tetrahydroquinoline 
• 50610-82-7 1,2,3,4-tetrahydro-2-(phenylmethyl)quinoline 
• 3678-74-8 2-(Diphenylmethyl)quinoline 
• 16576-25-3 2-benzoylquinoline 
• 23974-78-9 2-benzylquinoline 1-oxide 
• 95113-34-1 N-(2-quinolyl)-2-benzylidene-1,2-dihydroquinoline 
• 102181-27-1 (3-[2]quinolyl-3-phenyl-propyl)-dimethyl-amine 

Relevant articles and documents

Polar Effects in Free-Radical Reactions. Selectivity and Reversibility in the Homolytic Benzylation of Protonated Heteroaromatic Bases

The homolytic benzylation of protonated 4-cyanopyridine, quinoline, 2-methyl- and 4-methylquinoline, isoquinoline, and quinoxaline is investigated.The great influence of the polar effect and of the reversibility of the addition of the benzyl radical on the reaction selectivity is discussed.It is put forward the hypothesis that the HSAB principle can be extended to free-radical reactions when the polar effect is the dominant factor.

Mild Condition for the Deoxygenation of α-Heteroaryl-Substituted Methanol Derivatives

A mild condition via PPh3/I2/imidazole for the deoxygenation of substituted methanol derivatives has been identified. This metal-free process was found to proceed well on secondary or tertiary alcohols substituted with one or two heteroaryl groups, and it tolerates acid-sensitive heterocycles. This condition works for methanol derivatives substituted with 2-pyridyl, 4-pyridyl, or other heterocyclic groups, allowing the negative charge formed during the reaction to resonate to a nitrogen atom. Methanol derivatives substituted with 3-pyridyl or heterocyclic groups that do not allow the negative charge formed during the reaction to resonate to a nitrogen atom will not undergo deoxygenation under this condition.

A Metal- and Azide-free Oxidative Coupling Reaction for the Synthesis of [1,2,3]Triazolo[1,5-a]quinolines and their Application to Construct C?C and C-P Bonds, 2-Cyclopropylquinolines and Imidazo[1,5-a]quinolines

An iodine-promoted one-pot cascade oxidative annulation reaction has been developed for the synthesis of [1,2,3]triazolo[1,5-a]quinolines from methyl azaarenes and N-tosylhydrazines. The reaction has a broad substrate scope and can be easily scaled up to gram-scale. 1,2,3-Triazoles are an important skeletal structure for the construction of C?C and C?P bonds, 2-cyclopropylquinolines and imidazo[1,5-a]quinolines, for which different synthetic applications were explored. (Figure presented.).

Acylation of 2-benzylpyridine N-oxides and subsequent in situ [3,3]-sigamatropic rearrangement reaction

An effective method for the acylation of 2-benzylpyridine N-oxides and their fast in situ [3,3]-sigmatropic rearrangement was reported. This transformation has a wide substrate scope under mild conditions, giving moderate to excellent yields. The application for the synthesis of chiral phenyl-2-pyridylmethanol products was briefly explored. Furthermore, an interesting example of tandem substitution and in situ [3,3]-sigamatropic rearrangement of 2-benzylpyridine N-oxide with benzenecarboximidoyl chloride was reported.

Catalytic Selective Metal-Free Cross-Coupling of Heteroaromatic N-Oxides with Organosilanes

A metal-free, regioselective C-H functionalization of heteroaromatic N-oxides has been developed. The method enables the synthesis of various benzylated and alkynylated N-heterocycles in a transition-metal-free manner employing organosilanes as coupling partners. The unanticipated reactivity has been exploited for the synthesis of a number of symmetrical disubstituted acetylenes from ethynyltrimethylsilane via carbon-silicon bond metathesis.

Photocatalyzed ortho-Alkylation of Pyridine N-Oxides through Alkene Cleavage

A photocatalyzed reaction of pyridine N-oxides with alkenes gives ortho-alkylated pyridines with cleavage of the carbon–carbon double bond. Benzyl and secondary alkyl groups are incorporated at the ortho position of pyridines in one pot.

Palladium-Catalyzed Arylation of Benzylic C-H Bonds of Azaarylmethanes with Aryl Sulfides

Benzylic C-H arylation of azaarylmethanes with aryl sulfides has been developed by using a Pd-NHC catalyst and an amide base. Various azaarylmethanes and aryl sulfides were involved in the reaction to afford the corresponding diarylmethanes in good to excellent yields. Moreover, triarylmethane synthesis was accomplished through iterative arylations of 2- or 4-methylpyridine with two different aryl sulfides.

Synthesis of 2-Substituted Quinolines via Rhodium(III)-Catalyzed C–H Activation of Imidamides and Coupling with Cyclopropanols

An efficient synthesis of 2-substituted quinolines from readily available cyclopropanols and imidamides has been developed, where the cyclopropanol acts as a C3 synthon. With the assistance of a bifunctional imidamide directing group, the reaction occurred via sequential C–H/C–C cleavage and C–C/C–N bond formation. (Figure presented.).

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.

Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen

The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP-MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.