108934-21-0

Basic information

• Product Name: 2'-METHYL-BIPHENYL-4-CARBALDEHYDE
• Synonyms: TIMTEC-BB SBB007509;ASINEX-REAG BAS 08768156;CHEMBRDG-BB 4301965;AKOS BAR-0056;4-(2-METHYLPHENYL)BENZALDEHYDE;2'-METHYL-BIPHENYL-4-CARBALDEHYDE;2'-METHYL-BIPHENYL-4-CARBOXALDEHYDE;2'-METHYL[1,1'-BIPHENYL]-4-CARBALDEHYDE
• CAS NO: 108934-21-0
• Molecular Formula: C₁₄H₁₂O
• Molecular Weight: 196.24
• Mol File: 108934-21-0.mol
• Article Data: 38

Chemical Properties

• Boiling Point: 321.9 °C at 760 mmHg
• Flash Point: 164.6 °C
• Appearance: /
• Density: 1.074 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2'-METHYL-BIPHENYL-4-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-METHYL-BIPHENYL-4-CARBALDEHYDE(108934-21-0)
• EPA Substance Registry System: 2'-METHYL-BIPHENYL-4-CARBALDEHYDE(108934-21-0)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 22-36-51/53
• Safety Statements: 26-61
• HazardClass: IRRITANT
• Hazardous Substances Data: 108934-21-0(Hazardous Substances Data)

Usage

Description

2'-METHYL-BIPHENYL-4-CARBALDEHYDE is a diaryl compound characterized by its distinct chemical structure, which features a biphenyl core with a methyl group at the 2' position and a formyl group at the 4 position. 2'-METHYL-BIPHENYL-4-CARBALDEHYDE is known for its potential applications in various fields due to its unique properties and reactivity.

Uses

Used in Chemical Synthesis:
2'-METHYL-BIPHENYL-4-CARBALDEHYDE is used as a building block in the field of chemistry for the synthesis of more complex organic molecules. Its unique structure allows for further functionalization and the creation of a wide range of compounds with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2'-METHYL-BIPHENYL-4-CARBALDEHYDE is used as a key intermediate in the synthesis of various drugs and drug candidates. Its reactivity and structural features make it a valuable component in the development of new medications with potential therapeutic benefits.
Used in Material Science:
2'-METHYL-BIPHENYL-4-CARBALDEHYDE is also utilized in material science for the development of novel materials with specific properties. Its incorporation into polymers and other materials can lead to improved performance characteristics, such as enhanced stability, strength, or conductivity.
Used in Fragrance Industry:
In the fragrance industry, 2'-METHYL-BIPHENYL-4-CARBALDEHYDE is used as a component in the creation of various scents and perfumes. Its unique aroma profile contributes to the development of new and complex fragrances that can be used in a wide range of products.
Used in Dye and Pigment Industry:
2'-METHYL-BIPHENYL-4-CARBALDEHYDE is employed in the dye and pigment industry for the production of various colorants and dyes. Its chemical properties allow for the creation of stable and vibrant colors that can be used in a variety of applications, including textiles, plastics, and printing inks.

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Relevant articles and documents

Suzuki–Miyaura coupling reaction in water in the presence of robust palladium immobilized on modified magnetic Fe3O4 nanoparticles as a recoverable catalyst

Aryl halides and especially inactive aryl chlorides were coupled to benzenoid aromatic rings in a Suzuki–Miyaura coupling reaction in the absence of organic solvents and toxic phosphine ligands. The reaction was catalysed by a recoverable magnetic nanocatalyst, Pd@Fe3O4, in aqueous media. This method is green, and the catalyst is easily removed from the reaction media using an external magnetic field and can be re-used at least 10 times without any considerable loss in its activity. The catalyst was characterized using scanning and transmission electron microscopies, thermogravimetric analysis, inductively coupled plasma spectroscopy, Fourier transform infrared spectroscopy, CHN analysis, X-ray diffraction and vibrating sample magnetometry.

Palladium on carbon as a precatalyst for the Suzuki-Miyuara cross-coupling of aryl chlorides

Palladium on carbon is used as a precatalyst for Suzuki-Miyaura reaction of aryl chlorides and aryl boronic acids. An efficient catalyst system is obtained that allows the reaction of substrates that are difficult to couple under ligand free conditions. This includes electron rich and sterically hindered aryl chlorides as well as electron deficient and sterically hindered boronic acids. We have discovered that the amount of ligand needed to catalyze these reactions can be significantly decreased by incorporating an incubation period. This study also provides valuable insight into the mechanism of the Pd/C-catalyzed Suzuki-Miyaura cross-coupling. For example, mercury poisoning studies provide evidence that the active catalytic species is homogeneous. However, catalyst reuse and low metal contamination indicate that this system retains many of the advantages of a heterogeneous catalyst. From these results, a catalytic cycle is proposed.

N,N′-bridged binuclear NHC palladium complexes: A combined experimental catalytic and computational study for the Suzuki reaction

This work examines how N-donor bridged spacer ligands affect N-heterocyclic carbene (NHC) palladium complexes catalytic activities for Suzuki coupling reaction. Different degrees of structural flexibility binuclear NHC palladium complexes were synthesized. The more flexible nitrogen-based alkyl chain ligand shows similar performance with cycloamine counterparts in the Suzuki coupling reaction. Suzuki coupling examples were used in air and ambient temperature to reach moderate to completion yields in short time. Density functional theory calculations showed that the chelate effect, associated with a single Pd complex mechanism, plays a fundamental role in the pre-catalysis stage, supporting a reasonable of the kinetic activity observed experimentally.

Efficient salicylaldimine ligands for a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction

A series of salicylaldimine ligands were designed to promote palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. After a screening process, a ligand with a bulky 2,4-di-tert-butyl substituent on the salicyaldehyde backbone and cyclohexylamine moiety was found to serve as a good combination for this reaction in aqueous solutions of DMF. The protocol demonstrated a significant advance in the efficiency of the cross-coupling of aryl bromides and aryl chlorides with arylboronic acids to produce the desired biaryl products. Copyright 2012 John Wiley & Sons, Ltd. A systematic investigation on the effects of steric and electronic substituted salicylaldimine ligands and reaction conditions were tested in a Suzuki-Miyaura cross-coupling reaction. It demonstrated a significant advance in the efficiency of the cross-coupling of aryl bromides and aryl chlorides with arylboronic acids to produce the desired biaryl products. Copyright

A new precatalyst for the Suzuki reaction - A pyridyl-bridged dinuclear palladium complex as a source of mono-ligated palladiuin(0)

A dinuclear pyridyl-bridged palladium complex, trans-(P,N)-[PdBr(μ- C5H4N-C2,N)(PPh3)]2 1, was obtained from material isolated from the Suzuki cross-coupling reaction of 2-bromopyridine with 2,4-difluorophenylboronic acid in the presence of catalytic (PPh3)4Pd. Complex 1 is an effective precatalyst for the Suzuki cross-coupling reactions of a variety organoboronic acids and aryl bromides, and represents a useful source of mono-ligated palladium(0), "(Ph3P)Pd(0)".

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.

Magnetic covalently immobilized nickel complex: A new and efficient method for the Suzuki cross-coupling reaction

In this study, an efficient procedure was reported to prepare Fe3O4@SiO2 magnetic nanoparticles (MNPs) with immobilized nickel NPs. In order to increase the activity of this catalyst, creatine as a ligand with high content of nitrogen atoms was linked onto the magnetic core–shell structure. Then, Ni(II) ions were coordinated on the surface of the silica-coated MNPs and reduced to Ni(0) NPs to obtain the final catalyst. The catalytic activity of the prepared catalyst was studied for the synthesis of biaryl derivatives via the Suzuki–Miyaura cross-coupling reaction in high yields. The catalyst could also be recovered and reused with no loss of activity over five successful runs.