50670-55-8

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Cyanophenyl)benzaldehyde is used as a reagent for the synthesis of imidazolyl methylene biphenyls, which are inhibitors of CYP17. CYP17, or cytochrome P450 17A1, is an enzyme involved in steroidogenesis, playing a crucial role in the production of steroid hormones such as cortisol, aldosterone, and sex hormones. Inhibiting this enzyme can be beneficial in the treatment of conditions like prostate cancer, which often relies on androgen synthesis for growth and progression.
In the synthesis of imidazolyl methylene biphenyls, 4-(4-Cyanophenyl)benzaldehyde serves as a key intermediate, providing the necessary structural framework for the development of these inhibitors. 4-(4-Cyanophenyl)benzaldehyde's reactivity and functional groups make it a valuable component in the creation of new and effective pharmaceutical agents targeting CYP17.
Additionally, due to its unique structure, 4-(4-Cyanophenyl)benzaldehyde may have potential applications in other areas of the chemical and pharmaceutical industries, such as in the development of new materials, dyes, or other specialty chemicals. However, further research and development would be required to explore these possibilities fully.

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 87199-17-5 4-formylphenylboronic acid, 
• 50670-58-1 4-formyl-4'-bromobiphenyl 
• 623-00-7 4-bromobenzenecarbonitrile 
• 34421-94-8 4-bromobenzaldehyde diethyl acetal 
• 161664-51-3 C₉H₁₀BNO₂ 
• 1122-91-4 4-bromo-benzaldehyde 
• 104-88-1 4-chlorobenzaldehyde 
• 126747-14-6 4-cyanophenylboronic acid 
• 767-00-0 4-cyanophenol 
• 3058-39-7 4-iodobenzonitrile 
• 3218-36-8 4-Phenylbenzaldehyde 
• 98-80-6 phenylboronic acid 
• 1280078-62-7 4,5,7,8-tetrahydro-2-(4'-cyanophenyl)-6H-[1,3,6,2]dioxazaborocane 

Downstream Products

• 869767-76-0 2-(4'-cyanobiphenyl-4-yl)-1H-benzimidazole-5-carbonitrile 
• 154493-59-1 4-Cyano-4'-hydroxymethyl-biphenyl 
• 1380049-02-4 4'-{(R)-hydroxy[(S)-2-oxocyclopentyl]methyl}-1,1'-biphenyl-4-carbonitrile 
• 1221509-80-3 2,4,6-tris(4′-formyl-biphenyl-4-yl)-[1,3,5]triazine 
• 1609281-93-7 C₂₄H₁₉BF₂N₂O 
• 1268280-18-7 2-(4'-cyanobiphenyl)-4,5-bis[4-(N,N-dimethylamino)phenyl]-1H-imidazole 
• 847250-69-5 (5E)-(4'-cyanobiphenyl-4-ylmethylene)-3-(4-cyanophenyl)-4-hydroxyfuran-2(5H)-one 
• 869767-80-6 2-[4'-(N-hydroxyamidino)biphenyl-4-yl]-1H-benzimidazole-5-N-hydroxyamidine 

Relevant academic research and scientific papers

A Metal–Organic Supramolecular Box as a Universal Reservoir of UV, WL, and NIR Light for Long-Persistent Luminescence

Long persistent luminescence (LPL) materials have a unique photophysical mechanism to store light radiation energy for subsequent release. However, in comparison to the common UV source, white-light (WL) and near-infrared (NIR) excited LPL is scarce. Herein we report a metal–organic supramolecular box based on a D–π–A-type ligand. Owing to the integrated one-photon absorption (OPA) and two-photon absorption (TPA) attributes of the ligand, the heavy-atom effect of the metal center, as well as π-stacking and J-aggregation states in the supramolecular assembly, LPL can be triggered by all wavebands from the UV to the NIR region. This novel designed supramolecular kit to afford LPL by both OPA and TPA pathways provides potential applications in anti-counterfeiting, camouflaging, decorating, and displaying, among others.

Orthogonal insertion of lanthanide and transition-metal atoms in metal-organic networks on surfaces

The orthogonal coordinative properties of tetrapyrrole macrocycles and nitrile ligands have been used in a multistep procedure towards interfacial d-f hetero-bimetallic nanoarchitectures based on a free-base porphyrin derivative functionalized with meso-c

Pd(II)-Metalated and l-Proline-Decorated Multivariate UiO-67 as Bifunctional Catalyst for Asymmetric Sequential Reactions

The construction of a multifunctional catalyst for multistep sequentialtandem reactions at the molecular level faces a formidable challenge. Multivariate (MTV)-MOFs can provide a facile and tunable platform for rationally designing such multifunctional catalysts via grafting different catalytic groups on the bridging ligands. However, the related investigations are still limited. Here, Pd(II) and l-proline are metalated and decorated to organic linkers, respectively, to build a MTV-MOF, which is then successfully applied to sequential Suzuki Coupling/asymmetric Aldol reactions with satisfied coupling performance (yields up to 99%) and good enantioselectivities (eeanti up to 98%). Inductively coupled plasma optical emission spectrometer (ICP-OES) measurements of the supernatant and hot leaching test suggest the heterogeneous nature of the catalyst. Macrosubstrate tests verify that the reaction occurs inside the pores of the MOF. The heterogeneous catalyst can maintain structural stability and catalytic activity within three cycles. Graphic Abstract: Versatile Pd(II) and l-proline were metalated and decorated, respectively, into stable UiO-67 to construct bifunctional and heterogeneous multivariate MOF catalyst, which displayed efficient and recyclable catalytic activity in sequential Suzuki Coupling/asymmetric Aldol reactions.[Figure not available: see fulltext.]

Structure-Activity Relationship and Mode-Of-Action Studies Highlight 1-(4-Biphenylylmethyl)-1H-imidazole-Derived Small Molecules as Potent CYP121 Inhibitors

CYP121 of Mycobacterium tuberculosis (Mtb) is an essential target for the development of novel potent drugs against tuberculosis (TB). Besides known antifungal azoles, further compounds of the azole class were recently identified as CYP121 inhibitors with

Monosubstituted, Anionic Imidazolyl Ligands from N?H NHC Precursors and Their Activity in Pd-Catalyzed Cross-Coupling Reactions

We report that treatment of several 2-diphenylphosphinoimidazoles with Pd(II) salts generates monosubstituted N?H NHC?Pd complexes via insertion into the C?P bond. Removal of the N?H proton in situ leads to anionic (X-type) or imidazolyl-Pd complexes that are highly stable and catalytically active, achieving up to 340,000 turnovers at 1 ppm catalyst loading in Suzuki-Miyaura reactions. DFT-calculated Tolman electronic parameters for the sterically small ligands suggest that these ligands are significantly more donating than traditional NHCs, which provides a rationale for rapid cross-coupling catalysis. Excellent reactivity is also demonstrated in Sonogashira reactions. (Figure presented.).

Method for synthesizing biphenyl compound by taking suaeda salsa extract liquor as solvent

The invention discloses a method for synthesizing a biphenyl compound by using suaeda salsa extract as a solvent in the technical field of organic chemical synthesis, which comprises the following steps: roasting suaeda salsa in a muffle furnace to obtain ash, dissolving the ash in distilled water, refluxing, cooling the solution, and filtering to obtain a faint yellow solution which is the suaedasalsa extract liquor; sequentially adding 1mmol of aryl halide, 1.1mmol of arylboronic acid, 0.001mmol to 0.01mmol of a catalyst and 4ml of the suaeda salsa extract liquor into a round-bottom flask,stirring at 100 DEG C to react for 2 hours, cooling the reactant to room temperature, filtering, mixing the obtained filter residue with a palladium catalyst to obtain a mixture; and dissolving the mixture in ethyl acetate, filtering to remove the palladium catalyst, and drying the filtrate by distillation to obtain the biphenyl compound. According to the scheme, a phosphine ligand, alkali and anadditive do not need to be added, a Suzuki reaction system with biomass extract as a reaction medium is adopted, and a green, simple, convenient and efficient method is provided for synthesizing biphenyl compounds.

Method for synthesizing biphenyl compound by taking phenol as raw material

The invention discloses a method for synthesizing a biphenyl compound by using phenol as a raw material in the technical field of organic chemical synthesis, which comprises the following steps: carrying out a mixed reaction process on phenol or substituted phenol, alkali and 50-90% ethanol aqueous solution, slowly introducing sulfonyl fluoride gas, and carrying out magnetic stirring reaction at normal temperature for 4-12 hours, adding arylboronic acid, alkali and a palladium catalyst into a round-bottom flask, continuing to react for 6-12 hours at normal temperature, after the reaction is finished, adding a saturated edible salt solution into the round-bottom flask, carrying out a water quenching reaction process to obtain a reaction mixture, extracting a reaction product from the reaction mixture by using ethyl acetate, combining organic phases, concentrating filtrate, and separating the concentrated filtrate by using column chromatography to obtain analytically pure biphenyl or terphenyl compounds. By using the method, on one hand, the production cost of the biphenyl compound is reduced, and on the other hand, the method also has a wide application prospect in the aspects of synthesis of natural products, medicines, pesticides, herbicides, polymer conduction materials, liquid crystal materials and the like.

Chiral Proline-Decorated Bifunctional Pd?NH2-UiO-66 Catalysts for Efficient Sequential Suzuki Coupling/Asymmetric Aldol Reactions

The design and development of site-isolating and multifunctional catalysts for multistep sequential reactions at the molecular level is a significant challenge. Herein, we first report bifunctional metal NPs?chiral MOFs catalysts for asymmetric sequential reactions. Pd nanoparticles and chiral proline were successfully added to NH2-UiO-66 to construct two chiral bifunctional catalysts, in which active Pd nanoparticles were encapsulated into the frameworks via the "bottle-around-ship" method, and chiral proline was introduced into NH2-UiO-66 by coordination to zirconium nodes and postsynthetic modification (PSM) of the organic linkers. The chiral proline-decorated bifunctional Pd?NH2-UiO-66 catalysts were applied to sequential Suzuki coupling/asymmetric aldol reactions with excellent coupling performance (yields up to 99.9%) and good enantioselectivities (eeanti values up to 97%). The heterogeneous catalyst by coordination of proline can be reused, and the reaction activity was not significantly reduced after four cycles.

Conjugated Macrocycle Polymer Nanoparticles with Alternating Pillarenes and Porphyrins as Struts and Cyclic Nodes

Conjugated macrocycle polymers (CMPs) integrated using the macrocyclic confinement effect make imposing restrictions feasible on the growth of metal nanoparticles with confined size and high dispersion. For a proof-of-concept exploration, a novel nanoscale CMP is reported, denoted as DMP[5]-TPP-CMP, comprising two representative types of macrocyclic compounds, i.e., pillararene and porphyrin, as alternating strut/node components in the skeleton. With abundant anchoring sites, CMP implanted with Pd nanoparticles (Pd@DMP[5]-TPP-CMP, Pd@CMP for short) is successfully obtained through a simple post-treatment, exhibiting remarkable catalytic activity in Suzuki–Miyaura coupling (SMC) and nitrophenol reduction. The as-prepared Pd@CMP material shows favorable performance in expediting the process of SMC with an appreciable yield even under mild conditions, as well as in facilitating the electron transfer process from borohydride to nitrophenol through metal–hydride complex to produce aminophenol with a very short transformation time of 3 min and superior apparent kinetic rate constant k app of 1.9 × 10?2 s?1, higher than most palladium supports. Significantly, this multifunctional Pd@CMP composite material not only enriches the family of CMPs, but also sheds light on the development of green catalysts with excellent stability and easy recyclability without deactivation.

Copper-Free Click Reaction Sequence: A Chemoselective Layer-by-Layer Approach

An additive-free chemoselective ligation of dual clickable building blocks is demonstrated. The challenge of balancing reactivity and stability was achieved by employing a small, electron-deficient tetrazine bearing an azido group and an enol ether functionalized cyclooctyne. The chemoselective sequence of strain-promoted azide-alkyne cycloaddition (SPAAC) and inverse-electron-demand Diels-Alder (IEDDA) reaction is demonstrated with a cholic acid derived triazide as a molecular surface model for layer-by-layer synthesis.