Bromotrifluoroethylene

Last updated
Bromotrifluoroethylene
Bromotrifluoroethylene.svg
Names
IUPAC name
bromotrifluoroethene
Other names
trifluorovinyl bromide, trifluorobromoethylene
Identifiers
ECHA InfoCard 100.009.045 OOjs UI icon edit-ltr-progressive.svg
UN number 2419
Properties
C2BrF3
Molar mass 160.921 g·mol−1
Appearancecolourless gas
Odor moldy, [1] phosgene-like [2]
Boiling point –2.5°C [2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
spontaneous polymerisation, flammable [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bromotrifluoroethylene (BTFE) is a halogenated ethylene derivative with the chemical formula F2CCBrF. It is a highly flammable colourless gas with a musty odour resembling phosgene. It can polymerise spontaneously. [3]

Contents

Preparation

Bromotrifluoroethylene can be prepared from chlorotrifluoroethylene with high yields: [3] [4]

It was first prepared by the Belgian chemist Frédéric Swarts in 1899. [5]

Reactions and uses

Bromotrifluoroethylene forms metal complexes with substituted phosphine compounds and platinum(II). [6]

BTFE can polymerise on standing. Spontaneous polymerisation may be inhibited by addition of tributylamine. [4] UV light and heat may accelerate polymerisation. [4] It participates in various co-polymerisation reactions. [2] BTFE telomers are oily liquids sold under the tradename BFC oil. The telomers can be prepared with fluorotrichloromethane or tetrachloromethane as telogens. If tetrachloromethane is used for the telomerisation, it will have -CCl3 terminals. [5] It is a useful reagent for the synthesis of trifluorovinyl compounds. [3]

Related Research Articles

<span class="mw-page-title-main">Acid–base reaction</span> Chemical reaction between an acid and a base

In chemistry, an acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their application in solving related problems; these are called the acid–base theories, for example, Brønsted–Lowry acid–base theory.

In chemistry, a half reaction is either the oxidation or reduction reaction component of a redox reaction. A half reaction is obtained by considering the change in oxidation states of individual substances involved in the redox reaction. Often, the concept of half reactions is used to describe what occurs in an electrochemical cell, such as a Galvanic cell battery. Half reactions can be written to describe both the metal undergoing oxidation and the metal undergoing reduction.

<span class="mw-page-title-main">Carbon tetrachloride</span> Chemical compound

Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also recognised by the IUPAC) is a chemical compound with the chemical formula CCl4. It is a non-flammable, dense, colourless liquid with a "sweet" chloroform-like odour that can be detected at low levels. It was formerly widely used in fire extinguishers, as a precursor to refrigerants and as a cleaning agent, but has since been phased out because of environmental and safety concerns. Exposure to high concentrations of carbon tetrachloride can affect the central nervous system and degenerate the liver and kidneys. Prolonged exposure can be fatal.

<span class="mw-page-title-main">Potassium chlorate</span> Chemical compound

Potassium chlorate is a compound containing potassium, chlorine and oxygen, with the molecular formula KClO3. In its pure form, it is a white crystalline substance. After sodium chlorate, it is the second most common chlorate in industrial use. It is a strong oxidizing agent and its most important application is in safety matches. In other applications it is mostly obsolete and has been replaced by safer alternatives in recent decades. It has been used

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

Hydrobromic acid is an aqueous solution of hydrogen bromide. It is a strong acid formed by dissolving the diatomic molecule hydrogen bromide (HBr) in water. "Constant boiling" hydrobromic acid is an aqueous solution that distills at 124.3 °C (255.7 °F) and contains 47.6% HBr by mass, which is 8.77 mol/L. Hydrobromic acid is one of the strongest mineral acids known.

<span class="mw-page-title-main">Hydrogen bromide</span> Chemical compound

Hydrogen bromide is the inorganic compound with the formula HBr. It is a hydrogen halide consisting of hydrogen and bromine. A colorless gas, it dissolves in water, forming hydrobromic acid, which is saturated at 68.85% HBr by weight at room temperature. Aqueous solutions that are 47.6% HBr by mass form a constant-boiling azeotrope mixture that boils at 124.3 °C (255.7 °F). Boiling less concentrated solutions releases H2O until the constant-boiling mixture composition is reached.

<span class="mw-page-title-main">Single displacement reaction</span> Type of chemical reaction

A single-displacement reaction, also known as single replacement reaction or exchange reaction, is a chemical reaction in which one element is replaced by another in a compound.

Trichlorofluoromethane, also called freon-11, CFC-11, or R-11, is a chlorofluorocarbon (CFC). It is a colorless, faintly ethereal, and sweetish-smelling liquid that boils around room temperature. CFC-11 is a Class 1 ozone-depleting substance which damages Earth's protective stratospheric ozone layer.

<span class="mw-page-title-main">Triphenylphosphine</span> Chemical compound

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

<span class="mw-page-title-main">Sulfur tetrafluoride</span> Chemical compound

Sulfur tetrafluoride is the chemical compound with the formula SF4. It is a colorless corrosive gas that releases dangerous HF upon exposure to water or moisture. Despite these unwelcome characteristics, this compound is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.

<span class="mw-page-title-main">Indium(III) chloride</span> Chemical compound

Indium(III) chloride is the chemical compound with the formula InCl3 which forms a tetrahydrate. This salt is a white, flaky solid with applications in organic synthesis as a Lewis acid. It is also the most available soluble derivative of indium. This is one of three known indium chlorides.

In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications.

In chemistry, a reaction intermediate, or intermediate, is a molecular entity arising within the sequence of a stepwise chemical reaction. It is formed as the reaction product of an elementary step, from the reactants and/or preceding intermediates, but is consumed in a later step. It does not appear in the chemical equation for the overall reaction.

<span class="mw-page-title-main">Caesium bromide</span> Chemical compound

Caesium bromide or cesium bromide is an ionic compound of caesium and bromine with the chemical formula CsBr. It is a white or transparent solid with melting point at 636 °C that readily dissolves in water. Its bulk crystals have the cubic CsCl structure, but the structure changes to the rocksalt type in nanometer-thin film grown on mica, LiF, KBr or NaCl substrates.

1,1,2-Trichloro-1,2,2-trifluoroethane, also called trichlorotrifluoroethane or CFC-113, is a chlorofluorocarbon. It has the formula Cl2FC−CClF2. This colorless, volatile liquid is a versatile solvent.

<span class="mw-page-title-main">Fluorine perchlorate</span> Chemical compound

Fluorine perchlorate, also called perchloryl hypofluorite is the rarely encountered chemical compound of fluorine, chlorine, and oxygen with the chemical formula ClO
4
F
or FOClO
3
. It is an extremely unstable gas that explodes spontaneously and has a penetrating odor.

<span class="mw-page-title-main">Hexachloropropene</span> Chemical compound

Hexachloropropene is a compound of chlorine and carbon with the linear formula CCl3CCl=CCl2. It is a colourless liquid at room temperature. It is toxic for humans.

<span class="mw-page-title-main">Hexafluorobutadiene</span> Chemical compound

Hexafluorobutadiene is an organofluorine compound with the formula (CF2=CF)2. A colorless gas, it has attracted attention as an etchant in microelectronics. It is the perfluoroanalogue of butadiene.

<span class="mw-page-title-main">2-Chloro-1,1-difluoroethylene</span> Chemical compound

2-Chloro-1,1-difluoroethene (also known as R 1122, u-HCFC-1122 or HCFO-1122) is a toxic unsaturated hydrochlorofluorocarbon which can be written as CF2=CHCl. The HCFO portion of the name stands for hydrochlorofluoroolefin. Another constitutional isomer of it, 1-chloro-1,2-difluoroethylene, is known as HCFO-1122a.

References

  1. Hazardous Substance Fact Sheet, New Jersey Department of Health PDF
  2. 1 2 3 Yaws, C. L., Braker, W. (2001). Matheson gas data book. Page 69
  3. 1 2 3 4 Arthur J. Elliott, Bromotrifluoroethylene in Kirk-Othmer Encyclopedia of Chemical Technology
  4. 1 2 3 Fluorine chemistry: a comprehensive treatment (1995), pages 479–480
  5. 1 2 Industrial Polymers and Radiation: Proceedings of the Symposium Held at Sardar Patel University, Vallabh Vidyanagar, Gujarat, February 12–14, 1979.
  6. V.A. Mukhedkar, B.J. Kavathekar, A.J. Mukhedkar, Reactions of metal complexes Rearrangement reactions of bromotrifluoroethylene-bis(substituted phosphine)-platinum (II), Journal of Inorganic and Nuclear Chemistry, Volume 37, Issue 2, February 1975, Pages 483-485