Carbon tetrabromide

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{{Chembox | Watchedfields = changed | verifiedrevid = 470603395 | ImageFile = Tetrabrommethan.svg | ImageFile_Ref = {{chemboximage|correct|??}} | ImageSize = 100 | ImageName = Stereo, skeletal formula of tetrabromomethane | ImageFileL1 = Carbon-tetrabromide-3D-balls.png | ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageNameL1 = Stereo, skeletal formula of tetrabromomethane | ImageFileR1 = Carbon-tetrabromide-3D-vdW.png | ImageFileR1_Ref = {{chemboximage|correct|??}} | ImageNameR1 = Spacefill model of tetrabromomethane | ImageFile2 = Carbon tetrabromide.png | ImageSize2 = 150px | PIN = Tetrabromomethane<ref>{{Cite web|title=carbon tetrabromide – Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/compound/11205|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=18 June 2012|location=USA|date=26 March 2005|at=Identification}}</ref> | OtherNames = {{Unbulleted list|Carbon(IV) bromide|Carbon bromide, neutral (1:4)|Carbon tetrabromide}}<ref>{{Cite web|title=Carbon compounds: carbon tetrabromide|url=http://www.webelements.com/compounds/carbon/carbon_tetrabromide.html|access-date=22 February 2013}}</ref> |Section1={{Chembox Identifiers | Abbreviations = R-10B4{{Citation needed|date=June 2012}} | CASNo = 558-13-4 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = NLH657095L | PubChem = 11205 | ChemSpiderID = 10732 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | EINECS = 209-189-6 | UNNumber = 2516 | MeSHName = carbon+tetrabromide | ChEBI = 47875 | ChEBI_Ref = {{ebicite|correct|EBI}} | RTECS = FG4725000 | Beilstein = 1732799 | Gmelin = 26450 | SMILES = BrC(Br)(Br)Br | StdInChI = 1S/CBr4/c2-1(3,4)5 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HJUGFYREWKUQJT-UHFFFAOYSA-N | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} }} |Section2={{Chembox Properties | C=1 | Br=4 | Appearance = Colorless to yellow-brown crystals | Odor = sweet odor | Density = 3.42 g mL⁻¹ | MeltingPtK = 367.6 | BoilingPtK = 462.8 | BoilingPt_notes = decomposes | VaporPressure = 5.33 kPa (at 96.3&nbsp;°C) | Solubility = 0.024 g/100 mL (30&nbsp;°C) | SolubleOther = soluble in ether, chloroform, ethanol | RefractIndex = 1.5942 (100&nbsp;°C) | MagSus = −93.73·10⁻⁶ cm³/mol }} |Section3={{Chembox Structure | CrystalStruct = Monoclinic | Coordination = Tetragonal | MolShape = Tetrahedron | Dipole = 0 D }} |Section4={{Chembox Thermochemistry | DeltaHf = 26.0–32.8 kJ mol⁻¹ | DeltaHc = −426.2–−419.6 kJ mol⁻¹ | DeltaGf = 47.7 kJ/mol | Entropy = 212.5 J/mol K | HeatCapacity = 0.4399 J K⁻¹ g⁻¹ }} |Section5={{Chembox Hazards | ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0474.htm inchem.org] | GHSPictograms = {{GHS corrosion}} {{GHS exclamation mark}} | GHSSignalWord = '''DANGER''' | HPhrases = {{H-phrases|302|315|318|335}} | PPhrases = {{P-phrases|261|280|305+351+338}} | NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0 | LD50 = {{Unbulleted list|56 mg kg⁻¹ <small>(intravenous, mouse)</small>|100 mg kg⁻¹ <small>(oral, rat)</small>}} | PEL = none<ref name=PGCH>{{PGCH|0106}}</ref> | REL = TWA 0.1 ppm (1.4 mg/m³) ST 0.3 ppm (4 mg/m³)<ref name=PGCH/> | IDLH = N.D.<ref name=PGCH/> | FlashPt = noncombustible | FlashPt_ref =<ref name=PGCH/> }} |Section6={{Chembox Related | OtherAnions = Carbon tetrafluoride <br /> Carbon tetrachloride <br /> Carbon tetraiodide | OtherCations = Silicon tetrabromide <br /> Germanium tetrabromide <br /> Tin(IV) bromide | OtherFunction_label = alkanes | OtherFunction = {{Unbulleted list|Dibromomethane|Bromoform|1,1-Dibromoethane|1,2-Dibromoethane|Tetrabromoethane}} }} }} '''Carbon tetrabromide''', CBr₄, also known as '''tetrabromomethane''', is a bromide of carbon. Both names are acceptable under IUPAC nomenclature. ==Production== CBr₄ can be obtained by the bromination of methane. The byproducts include other brominated methanes (methyl bromide, dibromomethane and bromoform) and hydrogen bromide. This process is analogous to the chlorination of methane: :Br₂ + ''hν'' → 2&nbsp;Br'''·'''; : Br'''·''' + CH₄ → '''·'''CH₃ + HBr. : '''·'''CH₃ + Br₂ → CH₃Br + Br'''·'''. : CH₃Br + Br'''·''' → '''·'''CH₂Br + HBr, : '''·'''CH₂Br + Br₂ → CH₂Br₂ + Br'''·''', : CH₂Br₂ + Br'''·''' → '''·'''CHBr₂ + HBr, : '''·'''CHBr₂ + Br₂ → CHBr₃ + Br'''·''', :CHBr₃ + Br'''·''' → '''·'''CBr₃ + HBr, : '''·'''CBr₃ + Br₂ → CBr₄ + Br'''·''' Halogen exchange of carbon tetrachloride with aluminium bromide gives higher yields with aluminium chloride as the byproduct:<ref>N. N. Greenwood, A. Earnshaw: ''Chemie der Elemente'', 1. Auflage, VCH, Weinheim 1988, ISBN 3-527-26169-9, S.&nbsp;359.</ref> : 4 AlBr₃ + 3 CCl₄ → 4 AlCl₃ + 3 CBr₄

==Physical properties== Tetrabromomethane has two polymorphs: crystalline II or β below 46.9&nbsp;°C (320.0&nbsp;K) and crystalline I or α above 46.9&nbsp;°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°.<ref name="chtas">F. Brezina, J. Mollin, R. Pastorek, Z. Sindelar. ''Chemicke tabulky anorganickych sloucenin'' (''Chemical tables of inorganic compounds''). SNTL, 1986.</ref> Bond energy of C–Br is 235 kJ.mol⁻¹.<ref name="chemelem">N. N. Greenwood, A. Earnshaw. ''Chemie prvku'' (''Chemistry of the Elements''). Informatorium, Prague, 1993.</ref>

Due to its symmetrically substituted tetrahedral structure, its dipole moment is 0 Debye. Critical temperature is 439&nbsp;°C (712&nbsp;K) and critical pressure is 4.26&nbsp;MPa.<ref name="chtas"/>

==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<ref>{{cite journal|doi=10.1103/PhysRevB.77.144205 |title=Coupled orientational and displacive degrees of freedom in the high-temperature plastic phase of the carbon tetrabromide α-CBr4 |first1=Jacob C. W. |last1=Folmer |first2=Ray L. |last2=Withers |first3=T. R. |last3=Welberry |first4=James D. |last4=Martin |journal=Physical Review B |volume=77 |article-number=144205 |date=2008-04-10}}</ref> 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 tetrahalomethanes. It is made via bromination of methane using HBr or Br₂. It can be also prepared by more economical reaction of tetrachloromethane with aluminium bromide at 100&nbsp;°C.<ref name="chemelem"/>

==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.<ref>{{Cite web |title=Carbon tetrabromide, puriss, 97% {{!}} Ottokemi™ |url=https://www.ottokemi.com/chemical-synthesis/carbon-tetrabromide.aspx |access-date=2024-05-12 |website=www.ottokemi.com}}</ref>

==References== {{Reflist}}

==External links== *{{ICSC|0474|04}} *{{PGCH|0106}} *[https://web.archive.org/web/20110716024412/http://siri.org/msds/mf/cards/file/0474.html MSDS at SIRI.org] *[Solidification Videos using CBr4 of John D. Hunt and Kenneth A. Jackson, 1966 Bell Labs https://www.youtube.com/watch?v=c25wQYdC6a4]

{{bromine compounds}} {{bromides}} {{Halomethanes}} {{Carbon compounds}}

Category:Nonmetal halides Category:Halomethanes Category:Bromoalkanes Category:Halogenated solvents