6175-14-0

Basic information

• Product Name: Benzene, 1,1'-ethenylidenebis[4-fluoro-
• CAS NO: 6175-14-0
• Molecular Formula: C14H10F2
• Molecular Weight: 216.23
• Mol File: 6175-14-0.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-ethenylidenebis[4-fluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-ethenylidenebis[4-fluoro-(6175-14-0)
• EPA Substance Registry System: Benzene, 1,1'-ethenylidenebis[4-fluoro-(6175-14-0)

Safety Data

• Hazardous Substances Data: 6175-14-0(Hazardous Substances Data)

Upstream product

• 339-26-4 1,1-bis-(4-fluoro-phenyl)-ethanol 
• 357-77-7 1,1-bis(4-fluorophenyl)prop-2-yn-1-ol 
• 65-85-0 benzoic acid 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 352-13-6 4-flourophenylmagnesium bromide 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 75-16-1 methylmagnesium bromide 
• 345-92-6 4,4'-Difluorobenzophenone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 210627-73-9 2-{[2,2-Bis-(4-fluoro-phenyl)-2-hydroxy-ethyl]-phenyl-phosphinoyl}-1,1-bis-(4-fluoro-phenyl)-ethanol 
• 462-06-6 fluorobenzene 
• 71-55-6 1,1,1-trichloroethane 
• 210627-89-7 2,2,6,6-Tetrakis-(4-fluoro-phenyl)-4-phenyl-1,5-dioxa-4λ⁵-phospha-spiro[3.3]heptane 
• 19493-09-5 Methylenetriphenylphosphorane 

Downstream Products

• 380-73-4 2,2-bis-(4-fluoro-phenyl)-cyclopropanecarboxylic acid ethyl ester 
• 362-88-9 2,2-bis-(4-fluoro-phenyl)-ethenesulfinic acid 
• 395-24-4 4,4'-(ethane-1,1-diyl)bis(1-fluorobenzene) 
• 345-92-6 4,4'-Difluorobenzophenone 
• 138534-90-4 Toluene-4-sulfonic acid 2,2-bis-(4-fluoro-phenyl)-ethyl ester 
• 133216-83-8 ethyl 5,5-bis(4-fluorophenyl)-2-methyl-4,5-dihydrofuran-3-carboxylate 

Relevant articles and documents

Selective synthesis of iminodioxaspirononanes and diazaspirononanes using formic acid-activated Mn(III) oxidation of N1,N3-disubstitued malonamides with 1,1-diarylethenes

The Mn(III)-based oxidation of N1,N3-disubstituted malonamides with alkenes by Kurosawa spirolactonization using malonic acid afforded iminodihydrofurans. A similar reaction with Mn(OAc)3, which was activated by HCO2

Electrochemical fluorosulfonylation of alkenes to access vicinal fluorinated sulfones derivatives

Herein, we report a practical and efficient fluorosulfonylation of the various alkenes with sulfonyl radical sources (RSO2NHNH2) and Et3N·3HF as cost-effective fluorination reagents under mild conditions. Remarkably, this

Intermolecular [4 + 2] process of N-acyliminium ions with simple olefins for construction of functional substituted-1,3-oxazinan-2-ones

An efficient approach to functionalized 4,6-disubstituted-and 4,6,6-trisubstituted-1,3-oxazinan-2-ones skeleton has been developed through the reaction of semicyclic N,O-acetals 4a and 4b with 1,1-disubstituted ethylenes 5 or 8. As a result of such a [4 +

Photochemical Formal (4 + 2)-Cycloaddition of Imine-Substituted Bicyclo[1.1.1]pentanes and Alkenes

Amines containing bridged bicyclic carbon skeletons are desirable building blocks for medicinal chemistry. Herein, we report the conversion of bicyclo[1.1.1]pentan-1-amines to a wide range of polysubstituted bicyclo[3.1.1]heptan-1-amines through a photochemical, formal (4 + 2)-cycloaddition of an intermediate imine diradical. To our knowledge, this is the first reported method to convert the bicyclo[1.1.1]pentane skeleton to the bicyclo[3.1.1]heptane skeleton. Hydrolysis of the imine products gives complex, sp3-rich primary amine building blocks.

Rhodium-Catalyzed meta-Selective C?H Carboxylation Reaction of 1,1-Diarylethylenes via Hydrorhodation-Rhodium Migration

A meta-selective C?H carboxylation reaction of 1,1-diarylethylene derivatives with CO2 by using a rhodium catalyst with NaOiPr as a stoichiometric reductant has been achieved. Together with hydrogenation of the ethylene moiety, a carboxyl group was introduced to the meta-position of the aryl ring with high selectivity over the ortho-positions. Experimental and computational mechanistic studies indicate that this carboxylation reaction proceeds via hydrorhodation on the ethylene moiety, followed by 1,4-rhodium migration and successive 1,2-rhodium migration on the aryl ring. The use of a bulky phosphine ligand seems to be the key to this unusual aryl-to-aryl 1,2-rhodium shift.

Photoinduced Hydroarylation and Cyclization of Alkenes with Luminescent Platinum(II) Complexes

Photoinduced hydroarylation of alkenes is an appealing synthetic strategy for arene functionalization. Herein, we demonstrated that aryl radicals generated from electron-deficient aryl chlorides/bromides could be trapped by an array of terminal/internal aryl alkenes in the presence of [Pt(O^N^C^N)] under visible-light (410 nm) irradiation, affording anti-Markovnikov hydroarylated compounds in up to 95 % yield. Besides, a protocol for [Pt(O^N^C^N)]-catalyzed intramolecular photocyclization of acrylanilides to give structurally diverse 3,4-dihydroquinolinones has been developed.

Direct Allylic C(sp3)?H and Vinylic C(sp2)?H Thiolation with Hydrogen Evolution by Quantum Dots and Visible Light

Direct allylic C?H thiolation is straightforward for allylic C(sp3)?S bond formation. However, strong interactions between thiol and transition metal catalysts lead to deactivation of the catalytic cycle or oxidation of sulfur atom under oxidative condition. Thus, direct allylic C(sp3)?H thiolation has proved difficult. Represented herein is an exceptional for direct, efficient, atom- and step-economic thiolation of allylic C(sp3)?H and thiol S?H under visible light irradiation. Radical trapping experiments and electron paramagnetic resonance (EPR) spectroscopy identified the allylic radical and thiyl radical generated on the surface of photocatalyst quantum dots (QDs). The C?S bond formation does not require external oxidants and radical initiators, and hydrogen (H2) is produced as byproduct. When vinylic C(sp2)?H was used instead of allylic C(sp3)?H bond, the radical-radical cross-coupling of C(sp2)?H and S?H was achieved with liberation of H2. Such a unique transformation opens up a door toward direct C?H and S?H coupling for valuable organosulfur chemistry.

Visible-Light-Induced Meerwein Fluoroarylation of Styrenes

An unprecedented approach for assembling a broad range of 1,2-diarylethane derivatives with fluorine-containing fully substituted carbon centers was developed. The protocol features straightforward operation, proceeds under metal-free condition, and accommodates a large variety of synthetically useful functionalities. The critical aspect to the success of this novel transformation lies in using aryldiazonium salts as both aryl radical progenitor and also as single electron acceptor which elegantly enables a radical-polar crossover manifold.

Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes

Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.

Direct 1,2-Dicarbonylation of Alkenes towards 1,4-Diketones via Photocatalysis

1,4-Dicarbonyl compounds are intriguing motifs and versatile precursors in numerous pharmaceutical molecules and bioactive natural compounds. Direct incorporation of two carbonyl groups into a double bond at both ends is straightforward, but also challenging. Represented herein is the first example of 1,2-dicarbonylation of alkenes by photocatalysis. Key to success is that N(n-Bu)4+ not only associates with the alkyl anion to avoid protonation, but also activates the α-keto acid to undergo electrophilic addition. The α-keto acid is employed both for acyl generation and electrophilic addition. By tuning the reductive and electrophilic ability of the acyl precursor, unsymmetric 1,4-dicarbonylation is achieved for the first time. This metal-free, redox-neutral and regioselective 1,2-dicarbonylation of alkenes is executed by a photocatalyst for versatile substrates under extremely mild conditions and shows great potential in biomolecular and drug molecular derivatization.