2116-65-6

Usage

Uses

Used in Organic Synthesis:
4-Benzylpyridine is used as a key intermediate for the synthesis of various organic compounds. Its unique structure allows it to be a valuable component in the creation of a wide range of molecules, contributing to the diversity of chemical products.
Used in Pharmaceutical Industry:
4-Benzylpyridine is used as an important raw material in the pharmaceutical industry. It plays a crucial role in the development of new drugs and medicines, thanks to its ability to be incorporated into complex molecular structures.
Used in Dyes:
In the dye industry, 4-Benzylpyridine is utilized as a vital component in the production of various types of dyes. Its chemical properties enable it to contribute to the color and stability of the dyes, making it an essential part of the manufacturing process.
Used in Agrochemicals:
4-Benzylpyridine is also employed in the agrochemical sector as a key raw material. It is used in the synthesis of various agrochemical products, such as pesticides and fertilizers, which are essential for maintaining agricultural productivity and crop protection.
Used in the Synthesis of Ifenprodil Hemitartrate:
4-Benzylpyridine is the key raw material for the synthesis of Ifenprodil hemitartrate, a drug with potential applications in the treatment of neurological disorders. Its role in the production of 4-Benzylpyridine highlights its importance in the pharmaceutical industry and the development of new therapeutic agents.

Preparation

4-Benzylpyridine is synthesized from benzyl chloride and pyridine.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 1889, 1962 DOI: 10.1021/jo01052a509

Safety Profile

Poison by ingestion andintravenous routes. A flammable material. Incompatible with oxidizers. When heated to decomposition it emitstoxic fumes of NOx.

Purification Methods

Dry it with NaOH for several days, then distil it from CaO under reduced pressure, and redistil the middle fraction. [Beilstein 20/7 V 561.]

InChI:InChI=1/C12H11N/c1-2-4-11(5-3-1)10-12-6-8-13-9-7-12/h1-9H,10H2

Upstream product

• 110-86-1 pyridine 
• 620-05-3 iodomethylbenzene 
• 101-82-6 2-Benzylpyridine 
• 81771-00-8 <(pyridin-4-yl)phenylmethyl>lithium 
• 7259-53-2 4-benzylpyridine N-oxide 
• 109-89-7 diethylamine 
• 14178-34-8 (E)-4-pyridylphenyl ketoxime 
• 67998-48-5 1-benzoyl-4-benzylidene-1,4-dihydro-pyridine 
• 67998-51-0 1-acetyl-4-benzylidene-1,4-dihydro-pyridine 
• 89818-48-4 4-[(phenylmethyl)sulfinyl]pyridine 
• 80880-47-3 4-Benzyl-4-(diisopropoxy-phosphoryl)-4H-pyridine-1-carboxylic acid ethyl ester 
• 6921-34-2 benzylmagnesium chloride 
• 464-05-1 pyridinium trifluroacetate 
• 108-88-3 toluene 

Downstream Products

• 75665-43-9 1,1'-Carbonyl-bis<4-benzyliden-1,4-dihydropyridin> 
• 75997-79-4 3-[1-Phenyl-1-pyridin-4-yl-meth-(Z)-ylidene]-3H-isobenzofuran-1-one 
• 127376-22-1 2-Benzyl-4a,5,10,11-tetraaza-benzo[b]fluorene 
• 114643-78-6 4-Benzyl-1-trimethylsilanyl-pyridinium; iodide 
• 86-73-7 9H-fluorene 
• 81771-00-8 <(pyridin-4-yl)phenylmethyl>lithium 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 107134-92-9 4-Benzyl-1-<(4-methylphenyl)(trimethylsilyloxy)methyl>pyridinium-trifluormethansulfonat 
• 144797-23-9 1,4-dibenzylpyridin-1-ium bromide 
• 67998-52-1 4-Benzyliden-1-cinnamoyl-1,4-dihydropyridin 
• 122027-50-3 4-<2-phenyl-2-(4-pyridinyl)ethyl>-1-tritylimidazole 
• 101-82-6 2-Benzylpyridine 
• 67998-48-5 1-benzoyl-4-benzylidene-1,4-dihydro-pyridine 
• 67998-49-6 4-Benzyliden-1,4-dihydro-1-(p-toluoyl)pyridin 

Relevant academic research and scientific papers

1-acyl-4-benzylpyridinium tetrafluoroborates: Stability, structural properties, and utilization for the synthesis of acyl fluorides

1-Acyl-4-benzylpyridinium salts 4 containing nonnucleophilic anions X- such as CF3SO3-, FSO3-, and BF4- can be generated quantitatively and in situ from 1-acyl-4-alkylidene-1,4-dihydropyridines 1a-f and the corresponding acid, HX. The BF4- salts reveal an interesting and unexpected thermal instability which allows the convenient synthesis of carboxylic acid fluorides 5b-f. This procedure offers advantages over known methods: All operations can be performed in a standard glass apparatus and do not require high pressures. The formation of RCOF 5 is assisted by the pyridine moiety of 4, which splits off and functions as a Lewis base to intercept the BF3 acid. The structural and electronic relationships as well as dominating differences between the very reactive cations of 4 and their almost 'inert' uncharged precursors, the dihydropyridines 1, are discussed both on the fundament of experimental evidence (X-ray structures of 1f and the extremely reactive and very labile 4f) and theoretical investigations (ab initio and DFT MO calculations).

Practical and Regioselective Synthesis of C-4-Alkylated Pyridines

The direct position-selective C-4 alkylation of pyridines has been a long-standing challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using prefunctionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C-4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple and scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci chemistry as a late-stage functionalization technique.

Tunable System for Electrochemical Reduction of Ketones and Phthalimides

Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.

Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles

Lewis basic salts promote benzyltrimethylsilane coupling with (hetero)aryl nitriles, sulfones, and chlorides as a new route to 1,1-diarylalkanes. This method combines the substrate modularity and selectivity characteristic of cross-coupling with the practicality of a base-promoted protocol. In addition, a Lewis base strategy enables a complementary scope to existing methods, employs stable and easily prepared organosilanes, and achieves selective arylation in the presence of acidic functional groups. The utility of this method is demonstrated by the synthesis of pharmaceutical analogues and its use in multicomponent reactions.

Selective transition metal-free aroylation of diarylmethanes with 2-acyl-imidazolium salts via acyl C–C bond cleavage

A highly chemoselective method is reported for the aroylation of simple diarylmethane derivatives via direct acyl C–C cleavage with 2-acyl-imidazolium salts under transition metal-free conditions. This represents a straightforward way to access a variety of sterically and electronically diverse 1,2,2-triarylethanones, a class of compounds with biological activities and various applications.

A Supramolecular Palladium Catalyst Displaying Substrate Selectivity by Remote Control

Inspired by enzymes such as cytochrome P-450, the study of the reactivity of metalloporphyrins continues to attract major interest in the field of homogeneous catalysis. However, little is known about benefitting from the substrate-recognition properties of porphyrins containing additional, catalytically relevant active sites. Herein, such an approach is introduced by using supramolecular ligands derived from metalloporphyrins customized with rigid, palladium-coordinating nitrile groups. According to different studies (NMR and UV/Vis spectroscopy, XRD, control experiments), the supramolecular ligands are able to accommodate pyridine derivatives as substrates inside the porphyrin pocket while the reactivity occurs at the peripheral side. By simply tuning a remote metal center, different binding events result in different catalyst reactivity, and this enzyme-like feature leads to high degrees of substrate selectivity in representative palladium-catalyzed Suzuki–Miyaura reactions.

Room temperature dehalogenation of (hetero)aryl halides with magnesium/methanol

Magnesium in methanol was found to be an effective and inexpensive reagent for the dehalogenation of (hetero)aryl chlorides, bromides and iodides under mild conditions. The halogen/hydrogen exchange proceeded at room temperature and tolerated functional groups such as esters, nitriles, alcohols, and alkenes.

Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C-C-Bond Metathesis

A light-induced C-C-σ-bond metathesis was achieved through transition-metal-free activation of an unstrained C(sp3)-C(sp3)-σ-bond in 1-benzyl-1,2,3,4-tetrahydroisoquinolines. A photoredox-mediated single-electron oxidation of these precursor amines yield radical cations which undergo a homolytic cleavage of a C(sp3)-C(sp3)-σ-bond rather than the well-known α-C-H-scission. The resulting carbon-centered radicals are used in the ipso-substitution of (hetero)aromatic nitriles proceeding through another single-electron transfer-mediated C-C-bond cleavage and formation.

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 4-benzylpyridines via Pd-catalyzed CH3-arylation of 4-picoline

A highly efficient synthesis of 4-benzylpyridines was developed via Pd-catalyzed C(sp3)-H arylation between 4-picoline and aryl halides. It was found that the best yields were achieved with a simple Pd(PPh3)4 catalyst and Cs2CO3 as the base. Compared with the known methods, our reaction does not require the use of a strong organometallic reagent as the base.