27645-60-9

Basic information

• Product Name: 4-CYANO-4'-METHOXYBENZOPHENONE
• Synonyms: 4-CYANO-4'-METHOXYBENZOPHENONE;4-[(4-Methoxyphenyl)carbonyl]benzonitrile;4-(4-methoxybenzoyl)Benzonitrile
• CAS NO: 27645-60-9
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.25
• Mol File: 27645-60-9.mol
• Article Data: 24

Chemical Properties

• Melting Point: 130-132 °C
• Boiling Point: 422.5°C at 760 mmHg
• Flash Point: 184.7°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 2.4E-07mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: 4-CYANO-4'-METHOXYBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANO-4'-METHOXYBENZOPHENONE(27645-60-9)
• EPA Substance Registry System: 4-CYANO-4'-METHOXYBENZOPHENONE(27645-60-9)

Safety Data

• Hazardous Substances Data: 27645-60-9(Hazardous Substances Data)

Usage

Preparation

Obtained by reaction of 4-methoxybenzoyl chloride with acetonitrile in the –presence of aluminium chloride in carbon disulfide at r.t. for 3 h (35%).

InChI:InChI=1/C15H11NO2/c1-18-14-8-6-13(7-9-14)15(17)12-4-2-11(10-16)3-5-12/h2-9H,1H3

Upstream product

• 6068-72-0 4-cyanobenzoyl chlorIde 
• 100-66-3 methoxybenzene 
• 3058-39-7 4-iodobenzonitrile 
• 14271-83-1 4-methoxybenzoyl cyanide 
• 82303-13-7 (4-methoxyphenyl)zinc(II) bromide 
• 201230-82-2 carbon monoxide 
• 5720-07-0 4-methoxyphenylboronic acid 
• 623-00-7 4-bromobenzenecarbonitrile 
• 7099-91-4 p-methoxybenzoylformic acid 
• 696-62-8 para-iodoanisole 
• 126747-14-6 4-cyanophenylboronic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 52898-49-4 4,N-dimethoxy-N-methylbenzamide 
• 100-09-4 4-methoxybenzoic acid 

Downstream Products

• 27645-61-0 4-(4-hydroxybenzoyl)benzonitrile 
• 78025-00-0 cis-1,2-di(4-methoxyphenyl)-1,2-di(4-cyanophenyl)ethylene 
• 78025-02-2 trans-1,2-di(4-methoxyphenyl)-1,2-di(4-cyanophenyl)ethylene 
• 67205-85-0 4-[4-(4-hydroxybenzyl)benzyl]heptane-3,5-dione 
• 67205-84-9 4-[4-(4-methoxybenzyl)benzyl]heptane-3,5-dione 
• 67205-89-4 4-(4-methoxybenzyl)benzoic acid 
• 67205-88-3 ethyl 4-(4-methoxybenzyl) benzoate 
• 30042-05-8 4-(diazo(4-methoxyphenyl)methyl)benzonitrile 
• 67205-87-2 4-(4-methoxy-benzoyl)-benzoic acid ethyl ester 
• 66938-67-8 4-(4-Amino-3-nitro-benzoyl)-benzonitrile 
• 118909-15-2 1-[2-hydroxy-3-propyl-4-({4-[4-(1H-tetrazol-5-yl)-benzoyl]phenoxy}methyl)phenyl]ethanone 
• 135312-33-3 4-[4-(4-Acetyl-3-hydroxy-2-propyl-benzyloxy)-benzoyl]-benzonitrile 

Relevant articles and documents

Tetra- And Dinuclear Palladium Complexes Based on a Ligand of 2,8-Di-2-pyridinylanthyridine: Preparation, Characterization, and Catalytic Activity

Complexation of L [L = 5-phenyl-2,8-di-2-pyridinyl-anthyridine] with [Pd(CH3CN)4](BF4)2 and [Pd(CH3CN)3Cl](BF4) in a molar ratio of 1:2 rendered the corresponding dinuclear complexes [Pd2L (CH3CN)4](BF4)4 (1) and [Pd2L (CH3CN)2Cl2](BF4)2 (2), respectively. However, treatment of L with (COD)PdCl2 followed by anion exchange yielded a tetranuclear complex [Pd4L3Cl4](PF6)4(4a). Structures of these complexes are characterized by both spectroscopy and X-ray crystallography. Interconversion of these three complexes was studied via the manipulation of stoichiometric ratio of ligand to metal precursor. The catalytic activity of these complexes for carbonylative Suzuki-Miyaura cross-coupling was investigated. Complex 2 shows an excellent catalytic activity on the reaction of aryl iodide with arylboronic acid in the presence of atmospheric pressure of CO to give the corresponding benzophenones.

Dirhodium-Catalyzed Enantioselective B?H Bond Insertion of gem-Diaryl Carbenes: Efficient Access to gem-Diarylmethine Boranes

The scarcity of reliable methods for synthesizing chiral gem-diarylmethine borons limits their applications. Herein, we report a method for highly enantioselective dirhodium-catalyzed B?H bond insertion reactions with diaryl diazomethanes as carbene precursors. These reactions afforded chiral gem-diarylmethine borane compounds in high yield (up to 99 % yield), high activity (turnover numbers up to 14 300), high enantioselectivity (up to 99 % ee) and showed unprecedented broad functional group tolerance. The borane compounds synthesized by this method could be efficiently transformed into diaryl methanol, diaryl methyl amine, and triaryl methane derivatives with good stereospecificity. Mechanistic studies suggested that the borane adduct coordinated to the rhodium catalyst and thus interfered with decomposition of the diazomethane, and that insertion of a rhodium carbene (generated from the diaryl diazomethane) into the B?H bond was most likely the rate-determining step.

Novel and efficient bridged bis(N-heterocyclic carbene)palladium(II) catalysts for selective carbonylative Suzuki–Miyaura coupling reactions to biaryl ketones and biaryl diketones

Bridged N,N′-substituted bisbenzimidazolium bromide salts (L1, L2, and L3) were synthesized and fully characterized. Reactions of palladium acetate with L1, L2, and L3 afforded corresponding new bridged bis(N-heterocyclic carbene)palladium(II) complexes (C1, C2, and C3) in high yields. The X-ray structure of complex C1 showed that the Pd(II) ion is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromido ligands are in the cis position, resulting in a distorted square planar geometry. The three Pd(NHC)2Br2 complexes C1, C2, and C3 were evaluated in carbonylative Suzuki–Miyaura coupling reactions of aryl boronic acids with aryl halides and displayed high catalytic activity with low catalyst loading. The coupling reactions of aryl bromides were selective towards the carbonylation product at higher carbon monoxide pressure.