Tetrabromomethane, CBr₄, also known as carbon tetrabromide, is a

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon mak ...

bromide A bromide ion is the negatively charged form (Br−) of the element bromine, a member of the halogens group on the periodic table. Most bromides are colorless. Bromides have many practical roles, being found in anticonvulsants, flame-retardant ...

. Both names are acceptable under

IUPAC nomenclature A chemical nomenclature is a set of rules to generate systematic names for chemical compounds. The nomenclature used most frequently worldwide is the one created and developed by the International Union of Pure and Applied Chemistry (IUPAC). T ...

Physical properties

Tetrabromomethane has two polymorphs: crystalline II or β below 46.9 °C (320.0 K) and crystalline I or α above 46.9 °C. Monoclinic polymorph has

space group In mathematics, physics and chemistry, a space group is the symmetry group of an object in space, usually in three dimensions. The elements of a space group (its symmetry operations) are the rigid transformations of an object that leave it uncha ...

''C2/c'' with

lattice constant A lattice constant or lattice parameter is one of the physical dimensions and angles that determine the geometry of the unit cells in a crystal lattice, and is proportional to the distance between atoms in the crystal. A simple cubic crystal has o ...

s: ''a'' = 20.9, ''b'' = 12.1, ''c'' = 21.2 (.10⁻¹ nm), β = 110.5°.F. Brezina, J. Mollin, R. Pastorek, Z. Sindelar. ''Chemicke tabulky anorganickych sloucenin'' (''Chemical tables of inorganic compounds''). SNTL, 1986.

Bond energy In chemistry, bond energy (''BE''), also called the mean bond enthalpy or average bond enthalpy is the measure of bond strength in a chemical bond. IUPAC defines bond energy as the average value of the gas-phase bond-dissociation energy (usually ...

of C-Br is 235 kJ.mol⁻¹.N. N. Greenwood, A. Earnshaw. ''Chemie prvku'' (''Chemistry of the Elements''). Informatorium, Prague, 1993. Due to its symmetrically substituted

tetrahedral In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all the ...

structure, its dipole moment is 0

Debye The debye (symbol: D) (; ) is a CGS unit (a non- SI metric unit) of electric dipole momentTwo equal and opposite charges separated by some distance constitute an electric dipole. This dipole possesses an electric dipole moment whose value is g ...

. Critical temperature is 439 °C (712 K) and critical pressure is 4.26 MPa.

Plastic crystallinity

The high temperature α phase is known as a

plastic crystal A plastic crystal is a crystal composed of weakly interacting molecules that possess some orientational or conformational degree of freedom. The name plastic crystal refers to the mechanical softness of such phases: they resemble waxes and are easil ...

phase. Roughly speaking, the CBr₄ are situated on the corners of the cubic unit cell as well as on the centers of its faces in an fcc arrangement. It was thought in the past that the molecules could rotate more or less freely (a 'rotor phase'), so that on a time average they would look like spheres. Recent work Coupled orientational and displacive degrees of freedom in the high-temperature plastic phase of the carbon tetrabromide α-CBr4 Jacob C. W. Folmer, Ray L. Withers, T. R. Welberry, and James D. Martin. Physical Review B 77 in press has shown, however, that the molecules are restricted to only 6 possible orientations ( Frenkel disorder). Moreover, they cannot take these orientations entirely independently from each other because in some cases the bromine atoms of neighboring molecules would point at each other leading to impossibly short distances. This rules out certain orientational combinations when two neighbor molecules are considered. Even for the remaining combinations displacive changes occur that better accommodate neighbor to neighbor distances. The combination of censored Frenkel disorder and displacive disorder implies a considerable amount of disorder inside the crystal which leads to highly structured sheets of diffuse scattered intensity in X-ray diffraction. In fact, it is the structure in the diffuse intensity that provides the information about the details of the structure.

Chemical reactions

In combination with

triphenylphosphine Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists ...

, CBr₄ is used in the

Appel reaction The Appel reaction is an organic reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride. The use of carbon tetrabromide or bromine as a halide source will yield alkyl bromides, whereas using carbo ...

, which converts alcohols to alkyl bromides. Similarly, CBr₄ is used in combination with

in the first step of the Corey-Fuchs reaction, which converts

aldehydes In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...

into terminal

alkynes \ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no ...

. It is significantly less stable than lighter

tetrahalomethane Tetrahalomethanes are fully halogenated methane derivatives of general formula CBrkCllFmInAtp, where:k+l+m+n+p=4Tetrahalomethanes are on the border of inorganic and organic chemistry, thus they can be assigned both inorganic and organic names by IU ...

s. It is made via

bromination In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polyme ...

of methane using HBr or Br₂. It can be also prepared by more economical reaction of

tetrachloromethane Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVACR) is an organic compound with the chemica ...

with

aluminium bromide Aluminium bromide is any chemical compound with the empirical formula AlBrx. Aluminium tribromide is the most common form of aluminium bromide. It is a colorless, sublimable hygroscopic solid; hence old samples tend to be hydrated, mostly as al ...

at 100 °C.

Uses

It is used as a solvent for greases, waxes, and oils, in plastic and rubber industry for blowing and

vulcanization Vulcanization (British: Vulcanisation) is a range of processes for hardening rubbers. The term originally referred exclusively to the treatment of natural rubber with sulfur, which remains the most common practice. It has also grown to includ ...

, further for polymerization, as a sedative and as an intermediate in manufacturing agrochemicals. Due to its non-flammability it is used as an ingredient in fire-resistant chemicals. It is also used for separating minerals because of its high density.

References

External links

* *
MSDS at SIRI.org
{{Carbon compounds Nonmetal halides Halomethanes Bromoalkanes Halogenated solvents