396-44-1

Basic information

• Product Name: 1,1'-Biphenyl, 3,3',5,5'-tetrakis(trifluoromethyl)-
• CAS NO: 396-44-1
• Molecular Formula: C16H6F12
• Molecular Weight: 426.204
• Mol File: 396-44-1.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 1,1'-Biphenyl, 3,3',5,5'-tetrakis(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Biphenyl, 3,3',5,5'-tetrakis(trifluoromethyl)-(396-44-1)
• EPA Substance Registry System: 1,1'-Biphenyl, 3,3',5,5'-tetrakis(trifluoromethyl)-(396-44-1)

Safety Data

• Hazardous Substances Data: 396-44-1(Hazardous Substances Data)

Usage

Type of compound

Tetrakis(trifluoromethyl) derivative of biphenyl

Physical state at room temperature

White solid

Solubility in water

Insoluble

Usage

Building block in organic synthesis

Applications

Production of pharmaceuticals, agrochemicals, and specialty chemicals

Chemical and physical properties

Imparts unique properties due to tetrakis(trifluoromethyl) group

Thermal and chemical stability

High, making it suitable as a flame retardant

Additional uses

Production of polymers and plastics as a flame retardant

Upstream product

• 200956-32-7 1-(benzyloxy)-2-bromo-4-(trifluoromethyl)benzene 
• 73852-19-4 3,5-bis-trifluromethylphenylboronic acid 
• 2830-53-7 1-(benzyloxy)-2-bromo-4-methylbenzene 
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• 123-31-9 hydroquinone 
• 2797-28-6 lithium tetrakis(pentafluorophenyl)borate 
• 79060-88-1 sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate 
• 15522-59-5 tetrabutylammonium tetraphenylborate 
• 17984-89-3 triethoxy(thiophen-2-yl)silane 
• 328-73-4 3,5-bis(trifluoromethyl)iodobenzene 
• 90-11-9 1-Bromonaphthalene 

Downstream Products

• 402-31-3 1,3-bis(trifluoromethyl)benzene 
• 478930-63-1 [Pt(bis(di-tert-butylphosphino)methane)(η2-(3,5,3',5'-tetrakis(trifluoromethyl)biphenyl))] 

Relevant articles and documents

Electrochemical instability of highly fluorinated tetraphenyl borates and syntheses of their respective biphenyls

Highly fluorinated tetraphenyl borate anions are of importance as weakly coordinating anions in metalorganic reactions. However, at high positive potentials their electrochemical stability in organic solvents is not sufficient. This was investigated by a comprehensive cyclic voltammetry study and can be used synthetically to generate highly fluorinated biphenyls.

Electrochemical Synthesis of Biaryls via Oxidative Intramolecular Coupling of Tetra(hetero)arylborates

We report herein versatile, transition metal-free and additive-free (hetero)aryl-aryl coupling reactions promoted by the oxidative electrocoupling of unsymmetrical tetra(hetero)arylborates (TABs) prepared from ligand-exchange reactions on potassium trifluoroarylborates. Exploiting the power of electrochemical oxidations, this method complements the existing organoboron toolbox. We demonstrate the broad scope, scalability, and robustness of this unconventional catalyst-free transformation, leading to functionalized biaryls and ultimately furnishing drug-like small molecules, as well as late stage derivatization of natural compounds. In addition, the observed selectivity of the oxidative coupling reaction is related to the electronic structure of the TABs through quantum-chemical calculations and experimental investigations.

Palladium-mediated radical homocoupling reactions: A surface catalytic insight

In this contribution, we report a palladium nanoparticle-promoted reductive homocoupling of haloarenes that proceeds efficiently to produce corresponding bis-aryls in moderate to excellent yields using relatively low catalyst loading (1 mol%), and exhibits broad functional group tolerance. This work sheds light on how the surface state of Pd(0) nanoparticles plays a crucial role in the reactivity of catalytic systems. Notably, the appropriate choice of palladium salts for the preparation of the preformed nanocatalysts was a key parameter having a major impact on the catalytic activity; thus, the effect of halide anions on the reactivity of the as-prepared palladium nanoparticles could be assessed, with iodide anions being capable of inhibiting the corresponding homocoupling reaction. The homocoupling reaction mechanism has been further studied by means of radical trap and electron paramagnetic resonance (EPR) experiments, revealing that the reaction proceeds via radical intermediates. Taking into account these data, a plausible reaction mechanism based on single-electron transfer processes on the palladium nanoparticle surface is discussed.