460-11-7

Usage

Uses

Used in Polymer Production:
(E/Z)-1-BROMO-2-FLUOROETHYLENE is used as a monomer in the production of polymers for various applications, including the creation of materials with specific properties such as enhanced chemical resistance or thermal stability.
Used in Organic Synthesis:
(E/Z)-1-BROMO-2-FLUOROETHYLENE serves as a versatile building block in organic synthesis reactions, allowing for the creation of a wide range of chemical compounds with diverse applications.
Used in Fluorinated Compound Synthesis:
As a precursor, (E/Z)-1-BROMO-2-FLUOROETHYLENE is utilized in the synthesis of other fluorinated compounds, which are valuable for their unique properties such as non-stick surfaces, refrigerants, and fire-suppressing agents.
Used in Research and Industrial Applications:
(E/Z)-1-BROMO-2-FLUOROETHYLENE is employed in research settings for studying chemical reactions and properties of fluorinated compounds. It is also used in industrial applications where its reactivity and ability to form new compounds are leveraged for the development of innovative products.

InChI:InChI=1/C2H2BrF/c3-1-2-4/h1-2H

Upstream product

• 358-97-4 1,2-bromofluoroethane 
• 359-19-3 1,1-dibromo-2,2-difluoroethane 
• 593-60-2 Vinyl bromide 
• 64-17-5 ethanol 
• 598-73-2 1-bromo-1,2,2-trifluoroethene 

Relevant academic research and scientific papers

Organocatalytic C?F Bond Activation with Alanes

Hydrodefluorination reactions (HDF) of per- and polyfluorinated olefins and arenes by cheap aluminum alkyl hydrides in non-coordinating solvents can be catalyzed by O and N donors. TONs with respect to the organocatalysts of up to 87 have been observed. Depending on substrate and concentration, high selectivities can be achieved. For the prototypical hexafluoropropene, however, low selectivities are observed (E/Z≈2). DFT studies show that the preferred HDF mechanism for this substrate in the presence of donor solvents proceeds from the dimer Me4Al2(μ-H)2?THF by nucleophilic vinylic substitution (SNV)-like transition states with low selectivity and without formation of an intermediate, not via hydrometallation or σ-bond metathesis. In the absence of donor solvents, hydrometallation is preferred but this is associated with inaccessibly high activation barriers at low temperatures. Donor solvents activate the aluminum hydride bond, lower the barrier for HDF significantly, and switch the product preference from Z to E. The exact nature of the donor has only a minimal influence on the selectivity at low concentrations, as the donor is located far away from the active center in the transition states. The mechanism changes at higher donor concentrations and proceeds from Me2AlH?THF via SNV and formation of a stable intermediate, from which elimination is unselective, which results in a loss of selectivity.

Efficient microscale preparation of isotopically enriched 1-[ 79Br]bromo-2-fluoroethylene, [79Br]BrHC=CHF

An efficient preparation of 1-[79Br]bromo-2-fliioroethylene, [79Br]BrHC= CHF, was carried out by a three-step procedure: (a) natural 1-bromo-2-fluoroethylene, BrHC=CHF, was iodinated to 1-fluoro-2-iodoethylene, FHC=CHI; (b) 1-fluoro-2-iodoethylene was 79Br2-brominated to 1,2-di[79Br]bromo-1-fluoro- 2-iodoethane, [79Br]BrFCHCH[79Br]BrI; and (c) 1,2-di[ 79Br]bromo-1-fluoro-2-iodoethane was dehalogenated to 1-[ 79Br]bromo-2-fluoroethylene, [79Br]BrHC=CHF. The yield of isolated product, on a 2-mmol scale, was 62% with respect to 79Br2. Copyright Taylor & Francis, Inc.

Experimental and theoretical studies of the vibrational spectra of cis-1-bromo-2-fluoroethene

The gas-phase infrared spectrum of cis-1-bromo-2-fluoroethene has been studied at low resolution in the range 200-6500cm-1, leading to a complete assignment of the fundamentals, except the lowest vibrational mode ν9 predicted at 167cm-1. The remaining vibrational structure has been mainly interpreted in terms of first overtone or two quanta combination bands. Isotopic 79/81Br shift has been observed only in the ν8 fundamental. The equilibrium structure and the quadratic force field have been investigated theoretically at CCSD(T) level of theory employing Dunning's correlation consistent triple-zeta basis set. Cubic and semidiagonal quartic force field have been calculated using second-order M?ller-Plesset perturbation theory and Ahlrich' split valence (SV) contracted basis set. After a minor scaled quantum mechanical (SQM) adjustment of the quadratic force constants, the vibrational analysis, based on the second-order perturbation theory, has been carried out with the calculated force constants.

Microscale Preparation of Isotopically Enriched 37ClHC=CHF

Chlorination of 1-bromo-2-fluoroethylene followed by reductive dehalogenation of the produced 1-bromo-1,2-dichloro-2-fluoroethane selectively affords 1-chloro-2-fluoroethylene. This process is suitable to produce 37Cl isotopically enriched ClHC=CHF on a convenient scale (3.8 mmol).

Displacement Reaction Dynamics of Fluorine Atoms with Vinyl Bromide Molecules

Reactive scattering of F atoms with C2H3Br molecules leading to both H and Br atom displacement has been studied at an initial translational energy E ca. 40 kJ mol-1 using a supersonic beam of F atoms seeded in He buffer gas.The center-of-mass angular distribution of C2H3F reactive scattering shows a sharp forward peak with a lower backward peak of relative intensity ca. 0.5.The product translational energy distribution peaks at a low fraction f'pk ca. 0.1 of the total available energy with a tail extending up to higher energy.The branching ratio ca. 10 strongly favors Br atom displacement.The H atom displacement pathway occurs in competition with F atom migration in the FCH2CHBr. radical formed by F atom addition to the C=C double bond.The Br atom displacement occurs in the .CH2CHBrF radical formed either by F atom migration from FCH2CHBr. or directly from F atom addition to the C=C double bond.In either case, Br atom displacement occurs rapidly compared with the rate of F atom migration over the potential energy barrier in the bridged configuration, resulting overall in a short-lived collision complex mechanism for the formation of C2H3F reaction products.

Vibrational Excitation of the Reaction between Vinyl Bromide and Fluorine in Solid Argon

A number of unsuccessful attempts to induce bimolecular addition reactions with selective vibrational excitation in cryogenic solids are reported here: 1,3-butadiene with Cl2, ClF, Br2, I2, and XeF2; vinyl chloride with F2.One system, vinyl bromide with fluorine in solid argon, did respond by showing reaction product growth upon laser excitation at 3116, 3098, 1849, 1808, and 1605 cm-1.Identification of reaction products suggests F2 addition across the double bond followed significantly by HF elimination but apparently without HBr elimination.Relative quantum yields display a monotonic dependence upon photon energy that is even more dramatic than that found earlier for the ethylene-fluorine reaction.Thus excitation of the C-H stretching modes either at 3116 or 3098 cm-1 is 102 times more effective than excitation at 1849 or 1848 cm-1 and 103 times more effective than at 1605 cm-1.