10540-33-7

Basic information

• Product Name: 3-(4-Fluorophenyl)benzonitrile
• Synonyms: 3-(4-Fluorophenyl)benzonitrile
• CAS NO: 10540-33-7
• Molecular Formula: C₁₃H₈FN
• Molecular Weight: 197.2077232
• Mol File: 10540-33-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 66.0-67.9 °C
• Boiling Point: 323.7±25.0 °C(Predicted)
• Appearance: /
• Density: 1.19±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3-(4-Fluorophenyl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-Fluorophenyl)benzonitrile(10540-33-7)
• EPA Substance Registry System: 3-(4-Fluorophenyl)benzonitrile(10540-33-7)

Safety Data

• Hazardous Substances Data: 10540-33-7(Hazardous Substances Data)

Upstream product

• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 100-47-0 benzonitrile 
• 150255-96-2 (3‐cyanophenyl)boronic acid 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 352-34-1 4-fluoro-1-iodobenzene 
• 6952-59-6 3-cyanobromobenzene 
• 214360-58-4 2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 352-33-0 1-Chloro-4-fluorobenzene 

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Expanding the synthetic potential of Mg-Zn hybrid organyl reagents (generated via transmetallation reactions), this study uncovers a versatile approach, involving a sequence of direct Zn-I exchange and Pd catalysed cross-coupling reactions which grants access to a wide range of asymmetric bis(aryls). By combining X-ray crystallography with ESI-MS and non-deuterium NMR spectroscopic studies, new light is shed on the heterobimetallic constitution of the intriguing organometallic species [(THF)4MgCl 2Zn(tBu)Cl] (1) and [{Mg2Cl3(THF) 6}+{ZntBu3}-] (2), formed through transmetallation of tBuMgCl with n equivalent amounts of ZnCl2 (n = 1 and 3 respectively). Operating by cooperative effects, alkyl-rich hybrid 2 can effectively promote direct Zn-I exchange reactions with aromatic halides in short periods of time at room temperature in THF solution. The structural elucidation of key organometallic intermediates involved in some of these Zn-I exchanges, provides new reactivity insights into how these bimetallic systems operate. Thus, while the reaction of 2 with 3 equivalents of 2-iodoanisole (3b) gives magnesium dizincate [{Mg(THF)6}2+{Zn(o-C 6H4-OMe)3}2-] (4) which demonstrates the 3-fold activation of the tBu groups attached to Zn in 2, using 2-iodobenzonitrile (3i), only two tBu groups react with the substrate, affording [(THF)4MgCl(NC-o-C6H4)ZnI(o-C 6H4-CN)(THF)] (7). In 7 Mg and Zn are connected by an aryl bridge, suggesting that the formation of contacted ion-pair hybrids may have a deactivating effect on the outcome of the Zn-I exchange process. A wide range of homoleptic tris(aryl) zincate intermediates have been prepared in situ and used as precursors in Pd catalysed cross-coupling reactions, affording bis(aryls) 6a-s in excellent yields under mild reaction conditions without the need of any additive or polar cosolvent such as NMP or DMI.

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