84750-93-6

Basic information

• Product Name: 1-BROMO-4-(2,2-DIFLUOROVINYL)BENZENE
• Synonyms: 1-bromo-4-(2,2-difluoroethenyl)-benzene;4-Bromo-β-difluorostyrene (stabilized with TBC);2-(4-BROMOPHENYL)-1,1-DIFLUOROETHYLENE;1-BROMO-4-(2,2-DIFLUOROVINYL)BENZENE;4-BROMO-BETA,BETA-DIFLUOROSTYRENE;4-Bromo-β,β-difluorostyrene (stabilized with TBC);4-Bromo-beta,beta-difluorostyrene (stabilized with TBC)
• CAS NO: 84750-93-6
• Molecular Formula: C₈H₅BrF₂
• Molecular Weight: 219.03
• Mol File: 84750-93-6.mol

Chemical Properties

• Boiling Point: 209.8°C at 760 mmHg
• Flash Point: 80.7°C
• Appearance: /
• Density: 1.57
• Vapor Pressure: 0.287mmHg at 25°C
• Refractive Index: 1.5420-1.5460
• Storage Temp.: Freezer
• CAS DataBase Reference: 1-BROMO-4-(2,2-DIFLUOROVINYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-4-(2,2-DIFLUOROVINYL)BENZENE(84750-93-6)
• EPA Substance Registry System: 1-BROMO-4-(2,2-DIFLUOROVINYL)BENZENE(84750-93-6)

Safety Data

• Hazardous Substances Data: 84750-93-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-BROMO-4-(2,2-DIFLUOROVINYL)BENZENE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
Similarly, in the agrochemical sector, 1-BROMO-4-(2,2-DIFLUOROVINYL)BENZENE serves as an intermediate in the production of different agrochemicals. Its role in this industry is vital for the creation of effective pesticides and other agricultural products that enhance crop protection and yield.

InChI:InChI=1/C8H5BrF2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-5H

Upstream product

• 19740-19-3 chlorodifluoroacetic acid lithium salt 
• 1122-91-4 4-bromo-benzaldehyde 
• 895164-05-3 1-(4-bromophenyl)-2,2-difluoro-2-(phenylsulfonyl)ethan-1-ol 
• 1895-39-2 sodium chlorodifluoroacetate 
• 1219454-89-3 2-((difluoromethyl)sulfonyl)pyridine 
• 75-61-6 dibromodifluoromethane 
• 1600503-70-5 potassium 2-pyridinyl sulfonyl-difluoroacetate 
• 115262-00-5 [chloro(difluoro)methyl]trimethylsilane 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 87189-16-0 potassium 2-bromo-2,2-difluoroacetate 
• 57477-93-7 hydrazone of p-bromobenzaldehyde 
• 873-75-6 4-bromobenzenemethanol 
• 19350-68-6 p-bromobenzaldehyde tosylhydrazone 
• 51044-13-4 4-bromobenzyl triphenylphosphonium bromide 

Downstream Products

• 155820-88-5 1-bromo-4-(2,2,2-trifluoroethyl)benzene 
• 1379771-31-9 2-(4-bromobenzyl)quinoline 
• 16532-79-9 4-Bromophenylacetonitrile 

Relevant articles and documents

Stereoselective formation of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem?difluoroalkenes with lithium organoborates

A method for stereoselective construction of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem?difluoroalkenes in mild conditions was described. The combination of lithium organoborate and ZnBr2 generated in situ lithium ar

Fluoride-Triggered Synthesis of 1-Aryl-2,2-difluoroalkenes via Desilylative Defluorination of (1-Aryl)-2,2,2-trifluoroethyl-silanes

An efficient route for the synthesis of 1-aryl-2,2-difluoroalkenes via 1,2-desilylative defluorination is disclosed. Only a catalytic amount of fluoride source is required to initiate the desilylation and afford gem-difluoroalkenes in very good to quantitative yields, using mild reaction conditions in dimethyl carbonate as a green solvent. This reaction uses (1-aryl)-2,2,2-trifluoroethyl-silanes, which are easily prepared via the insertion reaction of trifluoroethyl diazo alkanes into the Si-H bond of tertiary organosilanes. (1-Aryl)-perfluoroalkyl-silanes cleanly afford the corresponding (Z)-1-benzylideneperfluoroalkanes, which upon hydrodefluorination furnish the (E)-β(perfluoroalkyl)styrene derivatives with excellent yield and complete stereoselectivity. A one-pot system involving sequential insertion and desilylative-defluorination is also suitable for this transformation. This method demonstrates the usefulness of organosilanes toward the preparation of fluorinated alkenes as synthetically useful targets.

Acid-Catalyzed Hydrothiolation of gem-Difluorostyrenes to Access α,α-Difluoroalkylthioethers

The substitution of hydrogen atoms with fluorine in bioactive molecules can greatly impact physicochemical, pharmacokinetic, and pharmacodynamic properties. However, current synthetic methods cannot readily access many fluorinated motifs, which impedes utilization of these groups. Thus, the development of new methods to introduce fluorinated functional groups is critical for developing the next generation of biological probes and therapeutic agents. The synthesis of one such substructure, the α,α-difluoroalkylthioether, typically requires specialized conditions that necessitate early-stage installation. A late-stage and convergent approach to access α,α-difluoroalkylthioethers could involve nucleophilic addition of thiols across gem-difluorostyrenes. Unfortunately, under basic conditions, nucleophilic addition to gem-difluorostyrenes generates an anionic intermediate that can undergo facile elimination of fluoride to generate α-fluorovinylthioethers. To overcome this decomposition, we herein exploit an acid-based catalyst system to facilitate simultaneous nucleophilic addition and protonation of the unstable intermediate. Ultimately, the optimized mild conditions afford the desired α,α-difluoroalkylthioethers in high selectivity and moderate to excellent yields. These α,α-difluoroalkylthioethers are less nucleophilic and more oxidatively stable relative to nonfluorinated thioethers, suggesting the potential application of this unexplored functional group in biological probes and therapeutic agents.

Visible-light-promotedE-selective synthesis of α-fluoro-β-arylalkenyl sulfidesviathe deoxygenation/isomerization process

Regioselective synthesis of α-fluoro-β-arylalkenyl sulfides has been established withgem-difluoroalkenes and sodium sulfinates in a transition-metal-free manner. A series of control experiments were executed to demonstrate thiol radicals and anions as the proposed intermediates. Notably, regioselectiveZ→Eisomerization was achieved under green light irradiation in the absence of a photoinitiator.

-Annulation of gem-Difluoroalkenes and Pyridinium Ylides: Access to Functionalized 2-Fluoroindolizines

A [3 + 2]-annulation of gem-difluoroalkenes and pyridinium ylides was developed employing ambient air as the sole oxidant in an open-vessel manner, affording a series of multifunctionalized 2-fluoroindolizines in moderate to good yields. In this reaction, gem-difluoroalkene acts as a C2 synthon and entirely avoids the competitive addition-elimination process, which provides facile access to 2-fluoroindolizines.

A one-step synthesis of gem-difluoroolefins from alcohols

The development of efficient protocols for the synthesis of gem-difluoroolefins has received increasing attention. Given the ubiquity of hydroxyl group in biologically active molecules and synthetic intermediates, we developed a one-step protocol for the conversions of alcohols into gem-difluoroolefins. The reactions of alcohols with Ph3P+CF2CO2?/Burgess reagent in DMSO occurred smoothly to afford the final products in moderate to high yields. DMSO is not only necessary for the oxidation process, but also important for the stabilization of phosphonium ylide by trapping difluorocarbene.

Autocatalytic Synthesis of Thioesters via Thiocarbonylation of gem-Difluoroalkenes

Herein, we report a new method for the synthesis of acyethanethioates via thiocarbonylation of gem-difluoroalkenes with thiols. This reaction provides a new pathway to prepare thioesters under mild conditions without the use of any additives. Mechanistic

Organocatalytic strategy for hydrophenolation of gem-difluoroalkenes

Gem-difluoroalkenes are an easily accessed fluorinated functional group, and a useful intermediate for elaborating into more complex fluorinated compounds. Currently, most functionalization reactions of gem-difluoroalkenes, with or without a transition metal-based catalyst system, involve the addition or removal of a fluorine atom to generate trifluorinated or monofluorinated products, respectively. In contrast, we present a complementary “fluorine-retentive” reaction that exploits an organocatalytic strategy to add phenols across gem-difluoroalkenes to deliver β,β-difluorophenethyl arylethers. The products are produced in good to moderate yields and selectivities, thus providing a range of compounds that are underrepresented in the synthetic and medicinal chemistry literature.

Pd-Catalyzed Selective Carbonylation of gem-Difluoroalkenes: A Practical Synthesis of Difluoromethylated Esters

The first catalyst for the alkoxycarbonylation of gem-difluoroalkenes is described. This novel catalytic transformation proceeds in the presence of Pd(acac)2/1,2-bis((di-tert-butylphosphan-yl)methyl)benzene (btbpx) (L4) and allows for an efficient and straightforward access to a range of difluoromethylated esters in high yields and regioselectivities. The synthetic utility of the protocol is showcased in the practical synthesis of a Cyclandelate analogue using this methodology as the key step.

Direct α-Monofluoroalkenylation of Heteroatomic Alkanes via a Combination of Photoredox Catalysis and Hydrogen-Atom-Transfer Catalysis

In this study, a new C(sp3)-H monofluoroalkenylation reaction involving cooperative visible-light photoredox catalysis and hydrogen-atom-transfer catalysis to afford products generated by selective hydrogen abstraction and radical-radical cross-coupling was described. This mild, efficient reaction shows high regioselectivity for the α-carbon atoms of amines, ethers, and thioethers and thus allows the preparation of monofluoroalkenes bearing various substituents. The reaction was applied to two bioactive molecules, indicating its utility for late-stage monofluoroalkenylation of compounds with inert C(sp3)-H bonds.