405-99-2

Basic information

• Product Name: 4-Fluorostyrene
• Synonyms: P-FLUOROSTYRENE;1-fluoro-4-ethenylbenzene;1-Fluoro-4-vinylbenzene;para-Fluorostyrene;Styrene, p-fluoro-;4-Fluorostyrene, 97+%;4-Fluorostyrene,98+%;4-Fluorostyrene, stabilized, 97%
• CAS NO: 405-99-2
• Molecular Formula: C₈H₇F
• Molecular Weight: 122.14
• EINECS: 206-975-0
• Product Categories: Styrenes;monomer;Monomers;Polymer Science;Styrene and Functionalized Styrene Monomers;Fluorine series
• Mol File: 405-99-2.mol

Chemical Properties

• Melting Point: -36--33°C
• Boiling Point: 67 °C50 mm Hg(lit.)
• Flash Point: 80 °F
• Appearance: Clear colorless to very slightly yellow/Liquid
• Density: 1.024 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.17mmHg at 25°C
• Refractive Index: n20/D 1.514(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water.
• BRN: 1634203
• CAS DataBase Reference: 4-Fluorostyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluorostyrene(405-99-2)
• EPA Substance Registry System: 4-Fluorostyrene(405-99-2)

Safety Data

• Hazard Codes: F,Xi
• Statements: 10-36/37/38
• Safety Statements: 23-24/25-37/39-26-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 405-99-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Fluorostyrene is used as a key intermediate for the production of various organic compounds. Its unique chemical structure allows for the creation of a wide array of products, making it an essential component in this field.
Used in Pharmaceuticals:
In the pharmaceutical industry, 4-Fluorostyrene is utilized as a building block for the synthesis of various medicinal compounds. Its presence in the molecular structure can influence the properties and efficacy of the final drug, contributing to the development of novel therapeutic agents.
Used in Agrochemicals:
4-Fluorostyrene plays a vital role in the agrochemical sector as a starting material for the synthesis of various pesticides and other agricultural chemicals. Its incorporation into these products can enhance their effectiveness and selectivity, leading to improved crop protection and yield.
Used in Dyestuff:
In the dyestuff industry, 4-Fluorostyrene is employed as a precursor for the production of a variety of dyes and pigments. Its unique chemical properties enable the creation of vibrant and stable colorants that are used in various applications, such as textiles, plastics, and printing inks.

InChI:InChI=1/C8H7F/c1-2-7-3-5-8(9)6-4-7/h2-6H,1H2

Upstream product

• 593-60-2 Vinyl bromide 
• 1765-93-1 4-fluoroboronic acid 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 459-57-4 4-fluorobenzaldehyde 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 18511-62-1 4-fluorostyrene oxide 
• 459-56-3 4-fluorobenzylic alcohol 
• 67-71-0 dimethylsulfone 
• 403-41-8 1-(4-Fluorophenyl)ethanol 
• 1147550-11-5 ammonium thiocyanate 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 352-34-1 4-fluoro-1-iodobenzene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 2343-30-8 1-fluoro-4-(2-fluoroethyl)benzene 

Downstream Products

• 64-19-7 acetic acid 
• 109764-64-9 1,10-Dibrom<2.2>paracyclophan-1-en 
• 109764-63-8 1,9-Dibrom<2.2>paracyclophan-1-en 
• 109764-92-3 4'',5'-Bis(4-fluorphenyl)dibenzo<2.2>paracyclophan-1,9-dien-4',5''-dicarbaldehyd 
• 109764-93-4 5',5''-Bis(4-fluorphenyl)dibenzo<2.2>paracyclophan-1,9-dien-4,4''-dicarbaldehyd 
• 109764-88-7 C₃₈H₂₆F₂O₂ 
• 109764-89-8 C₃₈H₂₆F₂O₂ 
• 122445-13-0 1-Fluoro-4-(3-methyl-pentyl)-benzene 
• 263-06-9 6H,12H-Dibenzo<1,5>dithiocin 
• 120229-48-3 3-(4-Fluorphenyl)-3,4-Dihydro-2H-1-benzothiopyran 
• 120229-39-2 2-(4-Fluorphenyl)-3,4-dihydro-2H-1-benzothiopyran 
• 18511-62-1 (2S)-2-(4-fluorophenyl)oxirane 

Relevant articles and documents

Indene formation upon borane-induced cyclization of arylallenes, 1,1-carboboration, and retro-hydroboration

We herein report the reaction of arylallenes with tris(pentafluorophenyl)borane that yields pentafluorophenyl substituted indenes. The tris(pentafluorophenyl)borane induces the cyclization of the allene and transfers a pentafluorophenyl ring in the course of this reaction. A Hammett plot analysis and DFT computations indicate a 1,1-carboboration to be the C-C bond-forming step.

Copper-Catalyzed Sulfonylation of Cyclobutanone Oxime Esters with Sulfonyl Hydrazides

A copper-catalyzed radical cross-coupling of cyclobutanone oxime esters with sulfonyl hydrazides has been developed. The copper-based catalytic system proved crucial for cleavage of the C-C bond of cyclobutanone oximes and for selective C-S bond-formation involving persistent sulfonyl-metal radical intermediates. This protocol is distinguished by the low-cost catalytic system, which does not require ligand, base, or toxic cyanide salt, and by the use of readily accessible starting materials, as well as broad substrate scope, providing an efficient approach to various diversely substituted cyano-containing sulfones.

Electrochemical fluorosulfonylation of styrenes

An environmentally friendly and efficient electrochemical fluorosulfonylation of styrenes has been developed. With the use of sulfonylhydrazides and triethylamine trihydrofluoride, a diverse array of β-fluorosulfones could be readily obtained. This reaction features mild conditions and a broad substrate scope, which could also be conveniently extended to a gram-scale preparation.

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.

Polymerization of Allenes by Using an Iron(II) β-Diketiminate Pre-Catalyst to Generate High Mn Polymers

Herein, we report an iron(II)-catalyzed polymerization of arylallenes. This reaction proceeds rapidly at room temperature in the presence of a hydride co-catalyst to generate polymers of weight up to Mn=189 000 Da. We have determined the polymer structure and chain length for a range of monomers through a combination of NMR, differential scanning calorimetry (DSC) and gel permeation chromatography (GPC) analysis. Mechanistically, we postulate that the co-catalyst does not react to form an iron(II) hydride in situ, but instead the chain growth is proceeding via a reactive Fe(III) species. We have also performed kinetic and isotopic experiments to further our understanding. The formation of a highly unusual 1,3-substituted cyclobutane side-product is also investigated.

Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene

The use of vinyl electrophiles in synthesis has been hampered by the lack of access to a suitable reagent that is practical and of appropriate reactivity. In this work we introduce a vinyl thianthrenium salt as an effective vinylating reagent. The bench-stable, crystalline reagent can be readily prepared from ethylene gas at atmospheric pressure in one step and is broadly useful in the annulation chemistry of (hetero)cycles, N-vinylation of heterocyclic compounds, and palladium-catalyzed cross-coupling reactions. The structural features of the thianthrene core enable a distinct synthesis and reactivity profile, unprecedented for other vinyl sulfonium derivatives.

Boronic Acid Pairs for Sequential Bioconjugation

Boronic acids can play diverse roles when applied in biological environments, and employing boronic acid structures in tandem could provide new tools for multifunctional probes. This Letter describes a pair of boronic acid functional groups, 2-nitro-arylboronic acid (NAB) and (E)-alkenylboronic acid (EAB), that enable sequential cross-coupling through stepwise nickel- and copper-catalyzed processes. The selective coupling of NAB groups enables the preparation of stapled peptides, protein-protein conjugates, and other bioconjugates.

Mild and efficient desulfurization of thiiranes with MoCl5/Zn system

Desulfurization of a variety of thiiranes to alkenes occurs chemoselectively in high yields upon treatment with MoCl5/Zn system under mild conditions. The new methodology demonstrates high functional group tolerance toward chloro, bromo, fluoro, methoxy, ester, ether and keto groups.

Nickel-Catalyzed Reductive Cross-Coupling of Aryl Bromides with Vinyl Acetate in Dimethyl Isosorbide as a Sustainable Solvent

A nickel-catalyzed reductive cross-coupling has been achieved using (hetero)aryl bromides and vinyl acetate as the coupling partners. This mild, applicable method provides a reliable access to a variety of vinyl arenes, heteroarenes, and benzoheterocycles, which should expand the chemical space of precursors to fine chemicals and polymers. Importantly, a sustainable solvent, dimethyl isosorbide, is used, making this protocol more attractive from the point of view of green chemistry.

Controlling the Lewis Acidity and Polymerizing Effectively Prevent Frustrated Lewis Pairs from Deactivation in the Hydrogenation of Terminal Alkynes

Two strategies were reported to prevent the deactivation of Frustrated Lewis pairs (FLPs) in the hydrogenation of terminal alkynes: reducing the Lewis acidity and polymerizing the Lewis acid. A polymeric Lewis acid (P-BPh3) with high stability was designed and synthesized. Excellent conversion (up to 99%) and selectivity can be achieved in the hydrogenation of terminal alkynes catalyzed by P-BPh3. This catalytic system works quite well for different substrates. In addition, the P-BPh3 can be easily recycled.