1210-05-5

Usage

Uses

Used in Pharmaceutical Industry:
BIPHENYL-2,2'-DICARBOXALDEHYDE is used as a key intermediate in the synthesis of various pharmaceuticals due to its reactive aldehyde groups, which facilitate the formation of new chemical entities with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, BIPHENYL-2,2'-DICARBOXALDEHYDE is utilized as a building block for the development of new agrochemicals, contributing to the creation of more effective and targeted pest control solutions.
Used in Dye Industry:
BIPHENYL-2,2'-DICARBOXALDEHYDE is used as a precursor in the production of dyes, capitalizing on its aromatic structure to yield vibrant and stable colorants for various applications.
Used in Polymer and Resin Production:
BIPHENYL-2,2'-DICARBOXALDEHYDE is employed as a monomer in the synthesis of polymers and resins, enhancing the properties of these materials for use in coatings, adhesives, and composites.
Used in Fragrance and Flavor Industry:
BIPHENYL-2,2'-DICARBOXALDEHYDE is used as a fragrance and flavor intermediate for creating odorants in perfumes, soaps, and detergents, as well as in the formulation of additives for the food and beverage industry, due to its ability to impart distinctive scents and tastes.
Used in Material Science:
In the field of material science, BIPHENYL-2,2'-DICARBOXALDEHYDE is used as a precursor for developing novel materials with specific properties and functionalities, such as in the creation of advanced composites and specialty polymers.

Upstream product

• 64-17-5 ethanol 
• 92161-37-0 2,2′‐bis(dibromomethyl)‐1,1′‐biphenyl 
• 583-52-8 potassium oxalate 
• 26260-02-6 2-iodobenzaldehyde 
• 2510-71-6 cis-9,10-dihydroxy-9,10-dihydrophenanthrene 
• 546-67-8 lead(IV) tetraacetate 
• 71-43-2 benzene 
• 25061-61-4 trans-9,10-dihydroxy-3,4-dihydrophenanthrene 
• 85-01-8 phenanthrene 
• 3594-90-9 2,2'-bis(hydroxymethyl)biphenyl 
• 15930-53-7 6-bromo-3,4-methylenedioxybenzaldehyde 
• 92-52-4 biphenyl 
• 201230-82-2 carbon monoxide 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 37445-18-4 C₄₂H₃₄ 
• 20162-43-0 (9Z,13bZ)-Benzo[a,c]benzo[3,4]cyclobuta[1,2-f]cyclooctene 
• 3731-88-2 2,2'-Bis-(4-hydroxy-phenyliminomethyl)-biphenyl 
• 3525-64-2 2,2'-Bis-cyclohexyliminomethyl-biphenyl 
• 3887-39-6 2,2'-Bis-(4-ethoxycarbonyl-phenyliminomethyl)-biphenyl 
• 18773-63-2 2'-hydroxymethyl-biphenyl-2-carboxylic acid 
• 18442-29-0 2,2′-bis(ethynyl)-1,1′-biphenyl 
• 1426546-44-2 N-[4-(phenylcarbamoyl)phenyl]-1-(4-phenylphenyl)methanimine oxide 
• 1354648-71-7 C₄₆H₃₈N₄O₄ 
• 1638114-50-7 C₂₆H₂₂N₄ 
• 113361-69-6 (2E,2'E)-diethyl 3,3'-([1,1'-biphenyl]-2,2'-diyl)diacrylate 
• 484-17-3 9-Phenanthrol 
• 3887-34-1 2,2'-Bis-(4-carboxy-phenyliminomethyl)-biphenyl 
• 3525-53-9 2,2'-Bis-(4-methoxy-phenyliminomethyl)-biphenyl 

Relevant academic research and scientific papers

Mass spectra of the oxygenated products generated from phenanthrene under simulated environmental conditions

The photooxidation of phenanthrene under simulated environmental conditions to 9,10-epoxy-9,10-dihydrophenanthrene, among other oxygenated products, serves as a model for the conversion of polycyclic aromatic hydrocarbons to potentially mutagenic and/or carcinogenic products. The separation and identificiation were achieved by glass capillary gas chromatography mass spectrometry, and by comparison of gas chromatographic retention times and mass spectral fragmentation patterns with data observed for authentic samples obtained independently through synthesis or from commercial sources. The structural rearrangements of 2,2'-di-substituted biphenyls such as 2-formylbiphenyl-2'-carboxylic acid, 2,2'-diformyl biphenyl and diphenic acid anhydride, induced upon electron impact are investigated and discussed in detail. The mass spectral comparison of 9,10-epoxy-9,10-dihydrophenanthrene, a primary mammalian metabolite of phenanthrene, and certain other structural isomers was conducted and the results of this study suggest a mass spectral technique capable of differentiating arene oxides from oxepin, phenol and carbonyl isomers. A discussion of the potential impact of the sensitized photooxidation of more condensed environmental polycyclic aromatic hydrocarbon pollutants is presented and the role of bioactive arene oxides produced under such photooxidation conditions is also discussed. Related oxides of polycyclic aromatic hydrocarbons are known to be proximate carcinogens and/or mutagens generated by metabolic activation. The role and significance of solar induced oxidation in the weathering of petroleum hydrocarbons at air-sea interfaces and the incorporation of potentially bioactive organic residues in the food chain are also addressed.

Identification of a Surprising Boronic Acid Homocoupling Process in Suzuki-Miyaura Cross-Coupling Reactions Utilizing a Hindered Fluorinated Arene

The Suzuki-Miyaura cross-coupling reaction of 2-bromo-1,3-bis(trifluoromethyl)benzene with arylboronic acids was evaluated and determined to suffer from the formation of large amounts of boronic acid homocoupling products in conjunction with dehalogenation. Homocoupling product formation in this process likely occurs through a rare protonolysis/second transmetalation event rather than by the well-established mechanism requiring the involvement of O 2. The scope of this boronic acid homocoupling reaction was investigated and shown to predominate with electron-deficient arylboronic acids. Finally, a good yield of cross-coupling products could be obtained by employing dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (SPhos) as the ligand.

Oxidation of Polynuclear Aromatic Hydrocarbons using Ruthenium-Ion-Catalyzed Oxidation: The Role of Aromatic Ring Number in Reaction Kinetics and Product Distribution

Oxidation of aromatic hydrocarbons with differing numbers of fused aromatic rings (2–5), have been studied in two solvent environments (monophasic and biphasic) using ruthenium-ion-catalyzed oxidation (RICO). RICO reduces the aromaticity of the polyaromatic core of the molecule in a controlled manner by selective oxidative ring opening. Moreover, the nature of the solvent system determines the product type and distribution, for molecules with more than two aromatic rings. Competitive oxidation between substrates with different numbers of aromatic rings has been studied in detail. It was found that the rate of polyaromatic hydrocarbon oxidation increases with the number of fused aromatic rings. A similar trend was also identified for alkylated aromatic hydrocarbons. The proof-of-concept investigation provides new insight into selective oxidation chemistry for upgrading of polyaromatic molecules.

An efficient one-pot approach to phenanthrene derivatives using a catalyzed tandem Ullmann-pinacol coupling reaction

In the presence of catalyst (Ph3P)2NiCl2 and reductant Zn, the Ullmann reactions of ortho-halo aryl aldehydes generate biaryl-dialdehydes and zinc halides. Subsequently, ZnX2 can catalyze the intramolecular pinacol coupling reaction of biaryl-dialdehydes to form 9,10-dihydrophenanthrene-9,10-diols. One-pot synthesis of 9-phenanthrols can be achieved using this strategy.

Palladium/Sensory Component-Catalyzed Homocoupling Reactions of Aryl Halides

A novel and efficient catalyst system was developed for homocoupling reactions of aryl halides. The catalyst system consists of Pd(OAc) 2and the peppery sensory component of tobacco leaves. This is the first time that a sensory component has been used in an organic reaction. Experiments using the catalyst system showed that the reactions proceeded smoothly under air in the absence of both an additional ligand and a reductant. Furthermore, the catalyst system can be applied to the coupling reactions of hetaryl iodides. Many functional groups (including a hydroxy group) are tolerated.

Role of Copper Species in the Oxidative Dimerization of Arylboronic Acids: Synthesis of Symmetrical Biaryls

Certain Cu(I) and Cu(II) salts are able to mediate the dimerization of arylboronic acids in DMF. They provide the corresponding symmetrical biaryls in moderate to very good yields. It is possible to run the reaction catalytically under an oxygen atmosphere without a significant loss of yields.

Efficient and convenient method for workup of ozonolysis reaction using sodium hydrosulfite

An efficient and convenient method is reported for reductive workup of the ozon-olysis reaction using sodium hydrosulfite. Comparisons were made between triethylamine and methyl sulfide for their use as a quenching reagent in the ozonolysis of a variety of alkenes. Taylor & Francis Group, LLC.

A novel and efficient method for the direct synthesis of pyrrolyl or indolyl substituted 9,10-dihydrophenanthren-9-ol analogues

A novel domino intramolecular [3+2] cycloaddtion and ring-opening aromatization process has been successfully developed for the efficient direct synthesis of pyrrolyl or indolyl substituted 9,10-dihydrophenanthren-9-ol analogues. And 1-(phenanthren-9-yl)-

Mechanistic investigations of a palladium-diene catalyzed Suzuki-Miyaura cross-coupling reaction

The mechanism of the first example of a palladium diene catalyzed asymmetric Suzuki-Miyaura cross-coupling reaction has been validated, with the key palladium intermediates captured and characterized. The identified species corresponding to each catalytic step were firmly associated with the diene ligand in our observations. In the ESI-MS/MS experiments by CID (collision-induced dissociation), the fragmentation of the gas-phase transmetalation species was consistent with the product-yielding process in the reductive elimination step and thus revealed the catalytically active species of the reaction system.

Convenient preparation of chiral trans-9,10-dihydrophenanthrene-9,10- diamine

Chiral trans-9,10-dihydrophenanthrene-9,10-diamine was conveniently prepared from biphenyl-2,2'-dialdehyde using intramolecular imino pinacol coupling and oxidative cleavage of aminoalcohol as key steps.