612-35-1

Usage

Uses

Used in Scientific Research:
2-Benzylbenzoic Acid is used as a research compound for its unique chemical properties, which make it a valuable asset in the development and understanding of new chemical reactions and processes.
Used in Chemical Reactions:
2-Benzylbenzoic Acid is used as a reactant in various chemical reactions due to its carboxylic acid and phenyl functional groups, which allow for a wide range of reactions and the synthesis of new compounds.
Used in Pharmaceutical Industry:
2-Benzylbenzoic Acid is used as an intermediate in the synthesis of pharmaceutical compounds, contributing to the development of new drugs and medications.
Used in Material Science:
2-Benzylbenzoic Acid is used in the development of new materials, such as polymers and composites, due to its aromatic stability and potential for chemical modification.

InChI:InChI=1/C14H12O2/c15-14(16)13-9-5-4-8-12(13)10-11-6-2-1-3-7-11/h1-9H,10H2,(H,15,16)

Upstream product

• 85-52-9 2-Benzoylbenzoic acid 
• 87-41-2 2-benzofuran-1(3H)-one 
• 71-43-2 benzene 
• 5398-11-8 3-phenylphthalide 
• 1586-00-1 2-(benzyl)benzyl alcohol 
• 56153-61-8 2-benzyl-benzonitrile 
• 604-61-5 ethyl 2-benzoylbenzoate 
• 716-43-8 dimethyl homophthalate 
• 108-94-1 cyclohexanone 
• 1586-01-2 (2-hydroxymethylphenyl)phenylmethanol 
• 7446-70-0 aluminium trichloride 
• 10034-85-2 hydrogen iodide 
• 7647-01-0 hydrogenchloride 
• 108-88-3 toluene 

Downstream Products

• 6962-60-3 2-benzyl-benzoic acid methyl ester 
• 118726-11-7 2-benzyl-benzoic acid-(2-morpholino-ethyl ester) 
• 102552-78-3 2-benzyl-benzoic acid-(2-morpholino-ethylamide) 
• 1585-99-5 2-benzylbenzoic acid ethyl ester 
• 61608-94-4 1-(2-(phenylmethyl)phenyl)ethanone 
• 56153-61-8 2-benzyl-benzonitrile 
• 40182-20-5 2-benzylbenzamide 
• 77979-28-3 9-(3-methylphenyl)anthracene 
• 1586-00-1 2-(benzyl)benzyl alcohol 
• 90-44-8 anthracen-9(10H)-one 
• 108011-67-2 2-cyclohexylmethyl-benzoic acid 
• 4992-42-1 (+/-)-trans-2-benzyl-cyclohexane-carboxylic acid-⁽¹⁾ 
• 4992-42-1 (+/-)-cis-2-benzyl-cyclohexane-carboxylic acid-⁽¹⁾ 
• 60456-75-9 1,1'-diphenyl-1H,1'H-[1,1']biisobenzofuranyl-3,3'-dione 

Relevant academic research and scientific papers

Palladium-Catalyzed Three-Component Coupling Reaction of o-Bromobenzaldehyde, N-Tosylhydrazone, and Methanol

A ligand-controlled palladium-catalyzed three-component reaction of o-bromobenzaldehyde, N-tosylhydrazone, and methanol is described. This reaction uses readily available compounds as starting materials while displaying a broad substrate scope and good functional group compatibility.

Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C-H Amidation

A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.

Pd-Catalyzed debenzylation and deallylation of ethers and esters with sodium hydride

Herein we demonstrate simply that the addition of Pd(OAc)2 as a promotor switches the reactivity of a commonly used base NaH to a nucleophilic reductant. The reactivity is engineered into a palladium-catalyzed reductive debenzylation and deallylation of aryl ethers and esters. This operationally simple, mild protocol displays a broad substrate scope and a broad spectrum of functional group tolerance (>50 examples) and high chemoselectivity toward aryl ethers over aliphatic structures. Moreover, the dual reactivity of NaH as a base and a reductant is demonstrated in efficient synthetic elaboration.

Controlled photo-flow oxidative reaction (UV-FOR) platform for ultra-fast phthalide and API synthesis

An integrated photo-flow oxidative reaction (UV-FOR) platform approach is presented for the synthesis of phthalides. The current protocol is catalyst-free, and uses economical and abundant hydro-carbons and hydrocarbon derivatives such as benzoic acid, benzene, and xylene, as starting materials. The reaction is performed using oxygen as a green oxidant in a time- and labour-efficient manner. This integrated approach has been shown to be successful in making a UV-FOR platform suitable for the on-demand synthesis of phthalides and their further syntheses to 2-arylmethylbenzoic acids and arylogous Michael addition products under relatively mild conditions. The current protocol was further extended to the gram scale synthesis of an ischemic stroke-relevant active pharmaceutical ingredient (API), 3-N-butylphthalide (NBP), in a continuous flow process.

Eosin Y as a Redox Catalyst and Photosensitizer for Sequential Benzylic C?H Amination and Oxidation

A new synergistic multicatalytic activation mode of eosin Y has been discovered by exploiting the redox potential of its ground state and excited state. This catalytic strategy proves to be an enabling tool for visible-light-driven sequential benzylic C?H amination and oxidation of o-benzyl-N-methoxyl-benzamides when using Selectfluor as a hydrogen atom transfer (HAT) reagent and O2 as oxidant. Efficient synthesis of a range of diversely functionalized 3-hydroxyisoindolinones can thus be achieved with good yields and selectivity at mild reaction conditions. Preliminary mechanistic studies and DFT calculations suggest that eosin Y works as a redox catalyst and photosensitizer.

Preparation method of carboxylic acid compound

The invention provides a preparation method of a carboxylic acid compound. The preparation method comprises the following step of taking a lactone component to react with hydrogen in the presence of a compound catalyst to obtain the carboxylic acid compound. The compound catalyst comprises a hydrogenation catalyst and Lewis acid. In the presence of the compound catalyst comprising the hydrogenation catalyst and the Lewis acid, the lactone component is subjected to hydrogenation ring-opening reaction to obtain the carboxylic acid compound. The preparation method has the advantages of moderate reaction conditions and high yield; compared with a traditional method, less byproducts are generated, green and chemical requirements are met and the industrial value is better.

A Comprehensive Study on Metal Triflate-Promoted Hydrogenolysis of Lactones to Carboxylic Acids: From Synthetic and Mechanistic Perspectives

Direct hydrogenolysis of lactone to carboxylic acid (i.e., hydrogenolysis of the Calkoxy-O bond with the carbonyl group untouched) is generally difficult, as the current strategies employing Br?nsted acids as the catalyst usually require harsh conditions such as a high temperature and a high H2 pressure. Herein, we report a developed solvent-free catalytic transformation, in which W(OTf)6 is believed to promote the hydrogenolysis process. This strategy could efficiently hydrogenate lactones to carboxylic acids under extra mild conditions (e.g., a reaction temperature of 2) and showed a broad substrate scope. In addition, the catalytic protocol can be further applied to the hydrogenolysis of polyhydroxyalkanoate, as a renewable polymer, to the corresponding straight-chain carboxylic acids. An extensive mechanistic study was subsequently performed, and the density functional theory calculations revealed a reaction pattern, including the complete cleavage of the C=O bond with the assistance of the W(OTf)6 catalyst. Moreover, the key intermediate created in the mechanism, as an oxonium with an OTf moiety, was successfully detected by electrospray ionization mass spectra. Through a comparison with the Br?nsted acid-catalyzed system, the study confirmed that the existence of the OTf moiety can significantly lower the barriers associated with the rearrangement and elimination processes. Meanwhile, emphasis was placed on the critical role that the anion plays, as well as the fact that the anion effect is directly related to the chemoselectivity.

Synthesis of annulated arenes and heteroarenes by hydriodic acid and red phosphorus mediated reductive cyclization of 2-(Hetero)aroylbenzoic acids or 3-(Hetero)arylphthalides

Annulated arenes and hetarenes were prepared in good to very good yields by hydriodic acid/red phosphorus mediated reductive cyclization of 3-(hetero)aryl phthalides. The reductive cyclization also proceeded successfully with 2-aroylbenzoic acids and 2-aroylnaphthoic acids.

Two-chamber hydrogen generation and application: Access to pressurized deuterium gas

Hydrogen and deuterium gas were produced and directly applied in a two-chamber system. These gaseous reagents were generated by the simple reaction of metallic zinc with HCl in water for H2 and DCl in deuterated water for D2. The setup proved efficient in classical Pd-catalyzed reductions of ketones, alkynes, alkenes, etc. in near-quantitative yields. The method was extended to the synthesis and isotope labeling of quinoline and 1,2,3,4-tetrahydroquinoline derivatives. Finally, CX-546 and Olaparib underwent efficient Ir-catalyzed hydrogen isotope exchange reactions.

Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere via N-H imines as an intramolecular directing group

Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere was developed starting from carbonitriles and Grignard reagents via N-H imine intermediates. The present process is characterized by the following two-step sequence in a one-pot manner: (1) addition of Grignard reagents to carbonitriles to form N-H imines and (2) benzylic C-H oxygenation (C=O bond formation) triggered by 1,5-hydrogen atom transfer with transient iminyl copper species.