460-11-7

Basic information

• Product Name: (E/Z)-1-BROMO-2-FLUOROETHYLENE
• Synonyms: (E/Z)-1-BROMO-2-FLUOROETHYLENE;1-BROMO-2-FLUOROETHYLENE;1-BROMO-2-FLUOROETHYLENE, MIXTURE OF ISOMERS;E/Z-1-Bromo-2-fluoroethylene 97%;E/Z-1-Bromo-2-fluoroethylene97%
• CAS NO: 460-11-7
• Molecular Formula: C2H2BrF
• Molecular Weight: 124.94
• Mol File: 460-11-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 36°C
• Appearance: /
• Density: 1.693 /cm³
• Refractive Index: 1.435
• CAS DataBase Reference: (E/Z)-1-BROMO-2-FLUOROETHYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: (E/Z)-1-BROMO-2-FLUOROETHYLENE(460-11-7)
• EPA Substance Registry System: (E/Z)-1-BROMO-2-FLUOROETHYLENE(460-11-7)

Safety Data

• Hazard Codes: Xi
• Statements: 10
• Safety Statements: 16
• RIDADR: 1993
• Hazardous Substances Data: 460-11-7(Hazardous Substances Data)

Usage

General Description

(E/Z)-1-Bromo-2-fluoroethylene, also known as bromofluoroethylene, is a chemical compound with the molecular formula C2H3BrF. It exists as a mixture of geometric isomers, referred to as the E and Z isomers, due to the presence of a double bond. (E/Z)-1-BROMO-2-FLUOROETHYLENE is used in the production of polymers and various organic synthesis reactions. It is also a precursor for the synthesis of other fluorinated compounds and is often used in research and industrial applications. (E/Z)-1-Bromo-2-fluoroethylene is a colorless, flammable gas and must be handled with caution due to its hazardous nature.

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

Upstream product

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

Relevant articles and documents

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.

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.

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.