216443-17-3

Usage

Uses

Used in Flavor and Fragrance Industry:
3'-METHYL [1,1'-BIPHENYL]-2-CARBOXALDEHYDE is used as a flavor and fragrance ingredient due to its strong odor, enhancing the sensory experience of various products in this industry.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3'-METHYL [1,1'-BIPHENYL]-2-CARBOXALDEHYDE serves as a potential candidate for the development of new pharmaceuticals, given its chemical structure and properties.
Used as a Starting Material in Organic Synthesis:
3'-METHYL [1,1'-BIPHENYL]-2-CARBOXALDEHYDE is used as a starting material for the synthesis of other organic compounds, taking advantage of its benzaldehyde group in various chemical reactions.

Upstream product

• 28987-79-3 m-tolylmagnesium bromide 
• 579-72-6 2-(dimethylamino)benzaldehyde 
• 71096-17-8 7-(3-Methylphenyl)-cyclohepta-1.3.5-trien 
• 591-17-3 meta-bromotoluene 
• 82632-38-0 N-tert-butyl-1-(2-methoxyphenyl)methanimine 
• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 6630-33-7 ortho-bromobenzaldehyde 
• 17933-03-8 m-tolylboronic acid 
• 89-98-5 2-chloro-benzaldehyde 
• 26260-02-6 2-iodobenzaldehyde 
• 5159-41-1 2-iodobenzyl alcohol 
• 88-67-5 2-Iodobenzoic acid 
• 615-37-2 ortho-methylphenyl iodide 
• 18982-54-2 o-bromobenzyl alcohol 

Downstream Products

• 1304460-87-4 C₂₁H₁₉NO₂S 
• 2523-39-9 3-methylfluorene 
• 1730-37-6 1-methylfluorene 
• 1399841-58-7 C₂₀H₁₈O 
• 1292302-47-6 3-methyl-9-[(4-methylphenyl)sulfonylamino]fluorene 

Relevant academic research and scientific papers

Electrochemical Decarboxylative Cyclization of α-Amino-Oxy Acids to Access Phenanthridine Derivatives

Phenanthridines are a class of useful heterocycles in the field of drug development. In this work, a method via electrochemical decarboxylative cyclization of α-amino-oxy acids to access phenanthridine derivatives was developed. This reaction proceeded th

Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement

Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.

Palladium-catalyzed synthesis of fluorenes by intramolecular c(sp 2)-h activation at room temperature

The synthesis of fluorenes by intramolecular Pd-catalyzed C(sp 2)-H activation of 2-arylbenzyl chlorides was conducted at room temperature by using commercially available triphenylphosphine and pivalic acid as ligands. The desired reactions proceeded efficiently at room temperature, and various substrates were converted into the corresponding fluorene derivatives in excellent yields.

Chromium-Catalyzed, Regioselective Cross-Coupling of C-O Bonds by Using Organic Bromides as Reactants

We report a chromium-catalyzed cross-coupling of C-O bonds with widely accessible organic bromides as reactants for the preparation of ortho -arylated or -alkylated aromatic aldehydes at room temperature. The use of metallic magnesium is essential for the reaction to occur, giving it an advantage over previous reactions involving Grignard reagents that have to be prepared separately from organic halides before the coupling.

Low-Valent, High-Spin Chromium-Catalyzed Cleavage of Aromatic Carbon-Nitrogen Bonds at Room Temperature: A Combined Experimental and Theoretical Study

The cleavage of aromatic carbon-nitrogen bonds catalyzed by transition metals is of high synthetic interest because such bonds are common in organic chemistry. However, few metal catalysts can be used to selectively break C(aryl)-N bonds in electronically neutral molecules. We report here the first low-valent, high-spin chromium-catalyzed cleavage of C(aryl)-N bonds in electronically neutral aniline derivatives at room temperature. By using simple and inexpensive chromium(II) chloride as precatalyst, accompanied by an imino auxiliary, the selective arylative and alkylative C-C coupling of C(aryl)-N bonds can be achieved. Crossover experiments indicate that a low-valent chromium species, formed in situ by reduction of CrCl2 with Grignard reagent, is responsible for the catalytic cleavage of C(aryl)-N bonds. DFT calculations show that facile insertion of the C(aryl)-N bond by chromium(0) can take place in a high-spin quintet (S = 2) ground state, whereas the lower-spin singlet (S = 0) and triplet (S = 1) states are inaccessible in energy. It was found that both donation of the sole paired d electrons in the d6 shell of high-spin chromium(0) to the antibonding orbital of the C(aryl)-N bond and the nitrogen ligating interaction to the metal center with its lone pair play important roles in the cleavage of the C(aryl)-N bond by the zerovalent chromium species.

An active catalytic system for Suzuki-Miyaura cross-coupling reactions using low levels of palladium loading

An easily available Pd(OAc)2/(2-(anthracen-9-yl)-1H-inden-3-yl) dicyclohexylphosphine/toluene/iPrOH/water catalytic system was developed, which shows high catalytic activity in the Suzuki-Miyaura cross-coupling reactions of a diverse array of aryl and heteroaryl chlorides with Pd loadings down to 0.01 mol%.

Gold-Catalyzed Oxidation Terminal Alkyne: An Approach to Synthesize Substituted Dihydronaphthalen-2(1H)-ones and Phenanthrenols

A facile gold-catalyzed oxidation terminal alkynes to synthesize substituted dihydronaphthalen-2(1H)-ones 3 and phenanthrenols 5 was realized. Various useful structures and drug precursors were generated in up to 99% yield under mild condition and low catalyst loading.

Silver-Catalyzed Tandem C=C Bond Hydroazidation/Radical Addition/Cyclization of Biphenyl Acetylene: One-Pot Synthesis of 6-Methyl Sulfonylated Phenanthridines

A silver-catalyzed tandem carbon-carbon triple bond hydroazidation, radical addition, and cyclization of biphenyl acetylene is described under mild conditions, leading to the formation of 6-methyl sulfonylated phenanthridines in good yields. In this novel cascade reaction, most of the atoms are incorporated into the product without cleavage of the C=C bond. Mechanistic studies suggest the reaction should proceed through an iminyl radical reactive intermediate.

(Biphenyl-2-alkyne) derivatives as common precursors for the synthesis of 9-iodo-10-organochalcogen-phenanthrenes and 9-organochalcogen-phenanthrenes

In this paper, we report our results on the cyclization of (biphenyl-2-alkyne) derivatives to give two different types of phenanthrene derivatives, 9-iodo-10-organochalcogen-phenanthrenes and 9-organochalcogen-phenanthrenes. The strategy for the synthesis was based on the use of electrophilic cyclization for the preparation of 9-iodo-10-organochalcogen-phenanthrenes and iron(iii) chloride/diorganyl diselenide-mediated intramolecular cyclization to prepare 9-organochalcogen-phenanthrenes. The effects of solvent, temperature, reaction time and stoichiometry on the efficiency of cyclization reactions were investigated. The standard reaction conditions were compatible with many functional groups in the substrates, such as methyl, chlorine, fluorine and methoxyl. This protocol was efficient for diorganyl diselenides and disulfides but ineffective for diorganyl ditellurides. The resulting phenanthrenes were further functionalized through Sonogashira reactions followed by the electrophilic cyclization reaction to give the selenophene-fused aromatic compounds.

2-Aryl-indenylphosphine ligands: Design, synthesis and application in Pd-catalyzed Suzuki-Miyaura coupling reactions

A focused library of phosphine ligands was constructed for structural optimization. The catalyst can be used to perform the Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl chlorides.