Tetrabromomethane

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Tetrabromomethane
Tetrabrommethan.svg
Stereo, skeletal formula of tetrabromomethane Carbon-tetrabromide-3D-balls.png
Stereo, skeletal formula of tetrabromomethane
Spacefill model of tetrabromomethane Carbon-tetrabromide-3D-vdW.png
Spacefill model of tetrabromomethane
Names
IUPAC name
Tetrabromomethane [1]
Other names
  • Carbon(IV) bromide
  • Carbon bromide
  • Carbon tetrabromide
[2]
Identifiers
3D model (JSmol)
AbbreviationsR-10B4[ citation needed ]
1732799
ChEBI
ChemSpider
ECHA InfoCard 100.008.355
EC Number 209-189-6
26450
MeSH carbon+tetrabromide
PubChem CID
RTECS number FG4725000
UN number 2516
Properties
CBr4
Molar mass 331.627 g·mol−1
AppearanceColorless to yellow-brown crystals
Odor sweet odor
Density 3.42 g mL−1
Melting point 94.5 °C; 202.0 °F; 367.6 K
Boiling point 189.7 °C; 373.4 °F; 462.8 Kdecomposes
0.024 g/100 mL (30 °C)
Solubility soluble in ether, chloroform, ethanol
Vapor pressure 5.33 kPa (at 96.3 °C)
-93.73·10−6 cm3/mol
1.5942 (100 °C)
Structure
Monoclinic
Tetragonal
Tetrahedron
0 D
Thermochemistry
0.4399 J K−1 g−1
212.5 J/mol K
26.0–32.8 kJ mol−1
47.7 kJ/mol
−426.2–−419.6 kJ mol−1
Hazards
Safety data sheet inchem.org
GHS pictograms GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
GHS signal word DANGER
H302, H315, H318, H335
P261, P280, P305+351+338
NFPA 704
Flammability code 0: Will not burn. E.g. waterHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no codeTetrabromomethane
0
2
0
Flash point noncombustible [3]
Lethal dose or concentration (LD, LC):
  • 56 mg kg−1(intravenous, mouse)
  • 1.8 g kg−1(oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
none [3]
REL (Recommended)
TWA 0.1 ppm (1.4 mg/m3) ST 0.3 ppm (4 mg/m3) [3]
IDLH (Immediate danger)
N.D. [3]
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tetrabromomethane, CBr4, also known as carbon tetrabromide, is a carbon bromide. Both names are acceptable under IUPAC nomenclature.

Carbon Chemical element with atomic number 6

Carbon is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Three isotopes occur naturally, 12C and 13C being stable, while 14C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the few elements known since antiquity.

A bromide is a chemical compound containing a bromide ion or ligand. This is a bromine atom with an ionic charge of −1 (Br); for example, in caesium bromide, caesium cations (Cs+) are electrically attracted to bromide anions (Br) to form the electrically neutral ionic compound CsBr. The term "bromide" can also refer to a bromine atom with an oxidation number of −1 in covalent compounds such as sulfur dibromide (SBr2).

Contents

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 C2/c with lattice constants: a = 20.9, b = 12.1, c = 21.2 (.10−1 nm), β = 110.5°. [4] Bond energy of C-Br is 235 kJ.mol−1. [5]

In materials science, polymorphism is the ability of a solid material to exist in more than one form or crystal structure. Polymorphism can potentially be found in any crystalline material including polymers, minerals, and metals, and is related to allotropy, which refers to chemical elements. The complete morphology of a material is described by polymorphism and other variables such as crystal habit, amorphous fraction or crystallographic defects. Polymorphism is relevant to the fields of pharmaceuticals, agrochemicals, pigments, dyestuffs, foods, and explosives.

Space group symmetry group of a configuration in space

In mathematics, physics and chemistry, a space group is the symmetry group of a configuration in space, usually in three dimensions. In three dimensions, there are 219 distinct types, or 230 if chiral copies are considered distinct. Space groups are also studied in dimensions other than 3 where they are sometimes called Bieberbach groups, and are discrete cocompact groups of isometries of an oriented Euclidean space.

Lattice constant

The lattice constant, or lattice parameter, refers to the physical dimension of unit cells in a crystal lattice. Lattices in three dimensions generally have three lattice constants, referred to as a, b, and c. However, in the special case of cubic crystal structures, all of the constants are equal and are referred to as a. Similarly, in hexagonal crystal structures, the a and b constants are equal, and we only refer to the a and c constants. A group of lattice constants could be referred to as lattice parameters. However, the full set of lattice parameters consist of the three lattice constants and the three angles between them.

Due to its symmetrically substituted tetrahedral structure, its dipole moment is 0 Debye. Critical temperature is 439 °C (712 K) and critical pressure is 4.26 MPa. [4]

Tetrahedron Polyhedron with 4 faces

In geometry, a tetrahedron, 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 ordinary convex polyhedra and the only one that has fewer than 5 faces.

The debye is a CGS unit of electric dipole moment named in honour of the physicist Peter J. W. Debye. It is defined as 1×10−18 statcoulomb-centimeters. Historically the debye was defined as the dipole moment resulting from two charges of opposite sign but an equal magnitude of 10−10 statcoulomb, which were separated by 1 Ångström. This gave a convenient unit for molecular dipole moments.

Plastic crystallinity

The high temperature α phase is known as a plastic crystal 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 [6] 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, CBr4 is used in the Appel reaction, which converts alcohols to alkyl bromides. Similarly, CBr4 is used in combination with triphenylphosphine in the first step of the Corey-Fuchs reaction, which converts aldehydes into terminal alkynes. It is significantly less stable than lighter tetrahalomethane bromination using HBr or Br2. It can be also prepared by more economical reaction of tetrachloromethane with aluminium bromide at 100 °C. [5]

Triphenylphosphine chemical compound

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 - often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

Appel reaction organic reaction that converts an alcohol into an alkyl chloride

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 carbon tetraiodide, methyl iodide or iodine gives alkyl iodides. The reaction is credited to and named after Rolf Appel, it had however been described earlier. The use of this reaction is becoming less common, due to carbon tetrachloride being restricted under the Montreal protocol.

Alcohol any organic compound in which the hydroxyl functional group (–OH) is bound to a saturated carbon atom

In chemistry, an alcohol is any organic compound in which the hydroxyl functional group (–OH) is bound to a carbon. The term alcohol originally referred to the primary alcohol ethanol, which is used as a drug and is the main alcohol present in alcoholic beverages. An important class of alcohols, of which methanol and ethanol are the simplest members, includes all compounds for which the general formula is CnH2n+1OH. It is these simple monoalcohols that are the subject of this article.

Uses

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

Vulcanization chemical process for converting natural rubber or related polymers into more durable materials

Vulcanization is a chemical process, invented by Charles Goodyear, used to harden rubber. Vulcanization traditionally referred to the treatment of natural rubber with sulfur and this remains the most common example, however the term has also grown to include the hardening of other (synthetic) rubbers via various means. Examples include silicone rubber via room temperature vulcanizing and chloroprene rubber (neoprene) using metal oxides.

A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are central nervous depressants and interact with brain activity causing its deceleration. Various kinds of sedatives can be distinguished, but the majority of them affect the neurotransmitter gamma-aminobutyric acid (GABA), which are brain chemicals performing communication between brain cells. In spite of the fact that each sedative acts in its own way, they produce beneficial relaxing effect by increasing GABA activity.

Related Research Articles

Bromine Chemical element with atomic number 35

Bromine is a chemical element with symbol Br and atomic number 35. It is the third-lightest halogen, and is a fuming red-brown liquid at room temperature that evaporates readily to form a similarly coloured gas. Its properties are thus intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος ("stench"), referencing its sharp and disagreeable smell.

Haloalkane

The haloalkanes are a group of chemical compounds derived from alkanes containing one or more halogens. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially and, consequently, are known under many chemical and commercial names. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes which contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.

In organic chemistry, an electrophile is an electron pair acceptor. Electrophiles are positively charged or neutral species having vacant orbitals that are attracted to an electron rich centre. It participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons. They appear to attract electrons as well and seem to behave as though they are partially empty. These partially empty substances thus require an electron rich center, and thus they are filled. Electrophiles can be observed as electron-sensitive or photo-sensitive.

Cristobalite silica mineral

Cristobalite is a mineral polymorph of silica that is formed at very high-temperatures. It is used in dentistry as a component of alginate impression materials as well as for making models of teeth

Hydrogen bromide chemical compound

Hydrogen bromide is the diatomic molecule with the formula HBr. It is a colorless compound and a hydrogen halide. Hydrobromic acid is a solution of HBr in water. Both the anhydrous and aqueous solutions of HBr are common reagents in the preparation of bromide compounds.

Bromine pentafluoride chemical compound

Bromine pentafluoride, BrF5, is an interhalogen compound and a fluoride of bromine. It is a strong fluorination reagent.

Aluminium bromide Chemical compound

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 aluminium tribromide hexahydrate (AlBr3·6H2O).

Copper(II) bromide chemical compound

Copper(II) bromide (CuBr2) is a chemical compound. It is used in photographic processing as an intensifier and as a brominating agent in organic synthesis.

Zirconium(IV) bromide is the inorganic compound with the formula ZrBr4. This colourless solid is the principal precursor to other Zr–Br compounds.

Thallium(I) bromide chemical compound

Thallium(I) bromide is a chemical compound of thallium and bromine with a chemical formula TlBr. It is used in room-temperature detectors of X-rays, gamma-rays and blue light, as well as in near-infrared optics.

Tungsten(V) bromide is the inorganic compound with the empirical formula WBr5. The compound consists of bioctahedral structure, with two bridging bromide ligands, so its molecular formula is W2Br10.

Antimony tribromide chemical compound

Antimony tribromide (SbBr3) is a chemical compound containing antimony in its +3 oxidation state.

Indium(I) bromide chemical compound

Indium(I) bromide is a chemical compound of indium and bromine. It is a red crystalline compound that is isostructural with β-TlI and has a distorted rock salt structure. Indium(I) bromide is generally made from the elements, heating indium metal with InBr3. It has been used in the sulfur lamp. In organic chemistry, it has been found to promote the coupling of α, α-dichloroketones to 1-aryl-butane-1,4-diones. Oxidative addition reactions with for example alkyl halides to give alkyl indium halides and with NiBr complexes to give Ni-In bonds are known. It is unstable in water decomposing into indium metal and indium tribromide. When indium dibromide is dissolved in water, InBr is produced as a, presumably, insoluble red precipitate, that then rapidly decomposes.

Strontium bromide chemical compound

Strontium bromide is a chemical compound with a formula SrBr2. At room temperature it is a white, odorless, crystalline powder. Strontium bromide burns bright red in a flame test. It is used in flares and also has some pharmaceutical uses.

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 easily deformed. If the internal degree of freedom is molecular rotation, the name rotor phase or rotatory phase is also used. Typical examples are the modifications Methane I and Ethane I. In addition to the conventional molecular plastic crystals, there are also emerging ionic plastic crystals, particularly organic ionic plastic crystals (OIPCs) and protic organic ionic plastic crystals (POIPCs). POIPCs are solid protic organic salts formed by proton transfer from a Brønsted acid to a Brønsted base and in essence are protic ionic liquids in the molten state, have found to be promising solid-state proton conductors for high temperature proton exchange membrane fuel cells. Examples include 1,2,4-triazolium perfluorobutanesulfonate and imidazolium methanesulfonate.

Cobalt(II) bromide chemical compound

Cobalt(II) bromide (CoBr2) is an inorganic compound. In its anhydrous form, it is a green solid that is soluble in water, used primarily as a catalyst in some processes.

Tetrabromoethane chemical compound

Tetrabromoethane (TBE) is a halogenated hydrocarbon, chemical formula C2H2Br4. Although three bromine atoms may bind to one of the carbon atoms creating 1,1,1,2-tetrabromoethane this is not thermodynamically favorable, so in practice tetrabromoethane is equal to 1,1,2,2-tetrabromoethane, where each carbon atom binds two bromine atoms.

Organobromine compounds, also called organobromides, are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.

Carbonyl bromide, also known as bromophosgene by analogy to phosgene, is an organic chemical compound. It is a decomposition product of halon compounds used in fire extinguishers.

Bromine azide chemical compound

Bromine azide is an explosive inorganic compound with the formula BrN3. It has been described as a crystal or a red liquid at room temperature. It is extremely sensitive to small variations in temperature and pressure, thus extreme caution must be observed when working with this reagent. This property of bromine azide has led to difficulty in discerning its crystal structure, with explosions occurring at Δp ≥ 0.05 Torr and also upon crystallization. Despite this, a crystal structure of bromine azide has been obtained using a miniature zone-melting procedure with focused infrared laser radiation. In contrast to IN3, which forms an endless chain-like structure upon crystallization, BrN3 forms a helical structure.

References

  1. "carbon tetrabromide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 18 June 2012.
  2. "Carbon compounds: carbon tetrabromide" . Retrieved 22 February 2013.
  3. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0106". National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 F. Brezina, J. Mollin, R. Pastorek, Z. Sindelar. Chemicke tabulky anorganickych sloucenin (Chemical tables of inorganic compounds). SNTL, 1986.
  5. 1 2 N. N. Greenwood, A. Earnshaw. Chemie prvku (Chemistry of the Elements). Informatorium, Prague, 1993.
  6. 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