6312-09-0

Basic information

• Product Name: 3-(2-Phenylethyl)pyridine
• Synonyms: 3-Phenethylpyridine;3-(2-PHENYLETHYL)PYRIDINE;3-PHENETHYLPYRIDINE 98.0%MIN
• CAS NO: 6312-09-0
• Molecular Formula: C₁₃H₁₃N
• Molecular Weight: 183.24902
• Product Categories: Pyridines derivates
• Mol File: 6312-09-0.mol

Chemical Properties

• Boiling Point: 281.9oC at 760 mmHg
• Flash Point: 115.3oC
• Appearance: /
• Density: 1.04g/cm3
• Vapor Pressure: 0.00592mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: 3-(2-Phenylethyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Phenylethyl)pyridine(6312-09-0)
• EPA Substance Registry System: 3-(2-Phenylethyl)pyridine(6312-09-0)

Safety Data

• Hazardous Substances Data: 6312-09-0(Hazardous Substances Data)

Usage

Uses

Used in Food and Beverage Industry:
3-(2-Phenylethyl)pyridine is used as a flavoring substance for its distinctive floral, sweet, and musky aroma. It is particularly favored in the production of alcoholic beverages such as whiskey, rum, and cognac, where it enhances the overall taste and sensory experience.
Used in Cosmetic and Personal Care Products:
In the cosmetic and personal care industry, 3-(2-Phenylethyl)pyridine is utilized for its fragrance properties. It contributes to the creation of appealing scents in a variety of products, including perfumes, lotions, and other skincare items, adding to their marketability and consumer appeal.
Used in Pharmaceutical Research:
3-(2-Phenylethyl)pyridine is studied for its potential therapeutic effects, which include anti-inflammatory and antioxidant properties. Researchers are exploring its possible applications in medicine, although its use in this field is subject to ongoing investigation and regulation due to concerns about its toxicity and environmental impact.

InChI:InChI=1/C13H13N/c1-2-5-12(6-3-1)8-9-13-7-4-10-14-11-13/h1-7,10-11H,8-9H2

Upstream product

• 1081-48-7 1-phenyl-2-(pyridin-3-yl)ethanone 
• 14627-92-0 2-phenyl-1-(pyridin-3-yl)ethanone 
• 108-99-6 3-Methylpyridine 
• 100-51-6 benzyl alcohol 
• 110-86-1 pyridine 
• 107264-16-4 diphenylmethanone O-(3-phenylpropanoyl) oxime 
• 626-60-8 3-Chloropyridine 
• 100-42-5 styrene 
• 2633-06-9 (E)-3-(2-phenylvinyl)pyridine 
• 100-54-9 pyridine-3-carbonitrile 
• 6921-34-2 benzylmagnesium chloride 
• 1120-90-7 3-iodopyridine 
• 17376-04-4 2-phenethyl iodide 
• 98-80-6 phenylboronic acid 

Downstream Products

• 54768-59-1 2-amino-5-(2-phenylethyl)pyridine 
• 91848-85-0 2-amino-3-(2-phenylethyl)pyridine 
• 91848-84-9 2-methyl-8-(2-phenylethyl)imidazo[1,2-a]pyridine-3-acetonitrile 
• 85333-07-9 2-Methyl-6-phenethyl-imidazo[1,2-a]pyridine 
• 96428-94-3 2-Methyl-8-(2-phenylethyl)-imidazo(1,2-a)pyridine 
• 136423-13-7 3-phenethylpiperidine 

Relevant articles and documents

Electrochemically Enabled, Nickel-Catalyzed Dehydroxylative Cross-Coupling of Alcohols with Aryl Halides

As alcohols are ubiquitous throughout chemical science, this functional group represents a highly attractive starting material for forging new C-C bonds. Here, we demonstrate that the combination of anodic preparation of the alkoxy triphenylphosphonium ion and nickel-catalyzed cathodic reductive cross-coupling provides an efficient method to construct C(sp2)-C(sp3) bonds, in which free alcohols and aryl bromides - both readily available chemicals - can be directly used as coupling partners. This nickel-catalyzed paired electrolysis reaction features a broad substrate scope bearing a wide gamut of functionalities, which was illustrated by the late-stage arylation of several structurally complex natural products and pharmaceuticals.

Copper(II)-catalyzed preparation of alkylindium compounds and applications in cross-coupling reactions both in aqueous media

An efficient water-based method for the synthesis of alkylindium compound in the presence of a catalytic amount of cheap and readily available CuSO4·5H2O (10 mol%) was developed. The thus-generated alkylindium compounds effectively underwent palladium-catalyzed cross-coupling reactions with a myriad of aryl halides in aqueous media, leading to the cross-coupled products in modest to high yields. The mildness of the formed alkyl organometallics allowed the tolerance to various important functional groups incorporated in both substrates of alkyl iodides and aryl halides.

Cobalt(II)-catalyzed preparation of alkylindium reagents and applications in cross-coupling with aryl halides

The direct insertion of indium powder into alkyl iodides was found to be efficiently catalyzed by a catalytic amount of cobalt(II) bromide (10 mol%). Upon subjection of the thus-formed alkylindium compounds to palladium-catalyzed cross-coupling reactions with a wide range of aryl halides, a series of cross-coupled products could be obtained in moderate to good yields with the tolerance to many important functional groups.

Preparation of Alkyl Indium Reagents by Iodine-Catalyzed Direct Indium Insertion and Their Applications in Cross-Coupling Reactions

An efficient method for the synthesis of alkyl indium reagent by means of an iodine-catalyzed direct indium insertion into alkyl iodide in THF is reported. The thus-generated alkyl indium reagents effectively underwent Pd-catalyzed cross-coupling reactions with various aryl halides, exhibiting good compatibility to a variety of sensitive functional groups. By replacing THF with DMA and using 0.75 equiv of iodine, less reactive alkyl bromide could be used as substrate for indium insertion with equal ease.

Cesium carbonate-catalyzed indium insertion into alkyl iodides and their synthetic utilities in cross-coupling reactions

A catalytic amount of cesium carbonate (10?mol%) was found to be capable of effectively catalyzing the insertion of indium powder into alkyl iodides. The thus-generated alkyl indium reagents could readily undergo palladium-catalyzed cross-coupling reactions with a wide variety of aryl halides, showing compatibility to a range of important functional groups.

Application of novel coupling reaction to preparing carbon-carbon bond structured compounds

The invention relates to application of a novel coupling reaction to preparing carbon-carbon bond structured compounds and mainly provides a reaction between alkyl indium compounds and halides. The reaction between the alkyl indium compounds and the halides can produce corresponding carbon-carbon structured products. The novel coupling reaction is high in process yield, broad in functional group tolerance and good in compatibility.

Bioinspired Palladium Nanoparticles Supported on Soil-Derived Humic Acid Coated Iron-Oxide Nanoparticles as Catalyst for C–C Cross-Coupling and Reduction Reactions

Abstract: Pd nanoparticles supported on humic acid-coated nanoferrites as magnetically-recoverable catalyst was expediently prepared from inexpensive precursors and characterized by techniques such as SEM, TEM, XPS, FT-IR, XRD, ICP-AES, EDX. The as made catalyst displayed an admirable catalytic activity towards the Suzuki–Miyaura cross-coupling reaction of aryl halides (or) aryl diazonium salts with aryl boronic acid in non-toxic solvent EtOH/water under mild conditions. The same catalyst showed high efficiency for the Heck reaction of aryl halides with styrene was carried out with high efficiency offering good yields under ligand-free conditions. Additionally, the reduction of olefins using molecular hydrogen was also achieved using the same catalyst under ambient and base-free conditions affording the products in good to excellent yields. The magnetic activity of nano-Fe3O4 allowed the effortless recovery of the catalyst and demonstrated subsequent recyclability up to 5 cycles without a significant loss in the activity. Graphical Abstract: [Figure not available: see fulltext.].

Deaminative Reductive Cross-Electrophile Couplings of Alkylpyridinium Salts and Aryl Bromides

A nickel-catalyzed reductive cross-coupling of alkylpyridinium salts and aryl bromides has been developed using Mn as the reductant. Both primary and secondary alkylpyridinium salts can be used, and high functional group and heterocycle tolerance is observed, including for protic groups. Mechanistic studies indicate the formation of an alkyl radical, and controlling its fate was key to the success of this reaction.

Catalytic Chemoselective and Stereoselective Semihydrogenation of Alkynes to E-Alkenes Using the Combination of Pd Catalyst and ZnI2

An efficient E-selective semihydrogenation of internal alkynes was developed under low dihydrogen pressure and low reaction temperature from commercially available reagents: Cl2Pd(PPh3)2, Zn0, and ZnI2. Kinetic studies and control experiments underline the significant role of ZnI2 in this process under H2 atmosphere, establishing that the transformation involves syn-hydrogenation followed by isomerization. This simple and easy-to-handle system provides a route to E-alkenes under mild conditions.

Ni-Catalyzed Electrochemical Decarboxylative C-C Couplings in Batch and Continuous Flow

An electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides is reported. The reaction proceeds under mild conditions in a divided electrochemical cell and employs a tertiary amine as the reductant. This decarboxylative C(sp3)-C(sp2) bond-forming transformation exhibits excellent substrate generality and functional group compatibility. An operationally simple continuous-flow version of this transformation using a commercial electrochemical flow reactor represents a robust and scalable synthesis of value added coupling process.