50670-55-8

Basic information

• Product Name: 4-(4-Cyanophenyl)benzaldehyde
• Synonyms: 4-(4-Cyanophenyl)benzaldehyde
• CAS NO: 50670-55-8
• Molecular Formula: C₁₄H₉NO
• Molecular Weight: 207.23
• Mol File: 50670-55-8.mol
• Article Data: 40

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(4-Cyanophenyl)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-Cyanophenyl)benzaldehyde(50670-55-8)
• EPA Substance Registry System: 4-(4-Cyanophenyl)benzaldehyde(50670-55-8)

Safety Data

• Hazardous Substances Data: 50670-55-8(Hazardous Substances Data)

Usage

Description

4-(4-Cyanophenyl)benzaldehyde, also known as 4''-Formyl-[1,1''-biphenyl]-4-carbonitrile, is an organic compound with the molecular formula C15H9NO. It is a derivative of benzaldehyde, featuring a cyano group and a biphenyl structure. 4-(4-Cyanophenyl)benzaldehyde is known for its potential applications in various chemical and pharmaceutical processes due to its unique structural properties.

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

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

Downstream Products

• 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 
• 869767-76-0 2-(4'-cyanobiphenyl-4-yl)-1H-benzimidazole-5-carbonitrile 

Relevant articles and documents

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.

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.]

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.

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.