| 词条 | Boron tribromide |
| 释义 |
| Verifiedfields = changed | verifiedrevid = 441021200 | Name = Boron tribromide | ImageFile = Boron-tribromide-3D-vdW.png | ImageName = Boron tribromide | IUPACName = Boron tribromide | OtherNames = Tribromoborane, Boron bromide |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 16787736 | InChI = 1/BBr3/c2-1(3)4 | SMILES = BrB(Br)Br | InChIKey = ILAHWRKJUDSMFH-UHFFFAOYAA | InChI1 = 1/B.3BrH/h;3*1H/q+3;;;/p-3 | InChIKey1 = LKBREHQHCVRNFR-DFZHHIFOAX | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/B.3BrH/h;3*1H/q+3;;;/p-3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = LKBREHQHCVRNFR-UHFFFAOYSA-K | CASNo = 10294-33-4 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|changed|FDA}} | UNII = A453DV9339 | PubChem = 25134 | RTECS = ED7400000 | EINECS = 233-657-9 | UNNumber = 2692 |Section2={{Chembox Properties | B=1|Br=3 | Appearance = Colorless to amber liquid | Odor = Sharp and irritating[1] | Density = 2.643 g/cm3 | Solubility = Reacts violently with water | SolubleOther = Soluble in ethanol, CCl4 | MeltingPtC = −46.3 | BoilingPtC = 91.3 | VaporPressure = 7.2 kPa (20 °C) | Viscosity = 7.31 x 10−4 Pa s (20 °C) | RefractIndex = 1.00207 |Section4={{Chembox Thermochemistry | DeltaHf = -0.8207 kJ/g | DeltaHc = | DeltaGf = | Entropy = 228 J/mol K | HeatCapacity = 0.2706 J/K |Section7={{Chembox Hazards | ExternalSDS = ICSC 0230 | GHSPictograms = {{GHS06|Acute Tox. 2}}{{GHS05|Skin Corr. 1B}} | GHSSignalWord = DANGER | HPhrases = {{H-phrases|330|300|314}} Within the European Union, the following additional hazard statement (EUH014) must also be displayed on labeling: Reacts violently with water. | NFPA-H = 3 | NFPA-F = 0 | NFPA-R = 2 | NFPA-S = W | FlashPt_notes= Noncombustible[1] | PEL = None[1] | REL = C 1 ppm (10 mg/m3)[1] | IDLH = N.D.[1] | MainHazards = Reacts violently with water, potassium, sodium, and alcohols; attacks metals, wood, and rubber[1] |Section8={{Chembox Related | OtherCompounds = Boron trifluoride Boron trichloride Boron triiodide }}Boron tribromide, BBr3, is a colorless, fuming liquid compound containing boron and bromine. It is decomposed by water and alcohols.[2] Chemical propertiesBoron tribromide is commercially available and is a strong Lewis acid. It is an excellent demethylating or dealkylating agent for the cleavage of ethers, also with subsequent cyclization, often in the production of pharmaceuticals.[3] The mechanism of dealkylation of tertiary alkyl ethers proceeds via the formation of a complex between the boron center and the ether oxygen followed by the elimination of an alkyl bromide to yield a dibromo(organo)borane. ROR + BBr3 → RO+(−BBr3)R → ROBBr2 + RBr Aryl methyl ethers (as well as activated primary alkyl ethers), on the other hand are dealkylated through a bimolecular mechanism involving two BBr3-ether adducts.[4] RO+(−BBr3)CH3 + RO+(−BBr3)CH3→ RO(−BBr3) + CH3Br + RO+(BBr2)CH3 The dibromo(organo)borane can then undergo hydrolysis to give a hydroxyl group, boric acid, and hydrogen bromide as products.[5] ROBBr2 + 3H2O → ROH + B(OH)3 + 2HBr It also finds applications in olefin polymerization and in Friedel-Crafts chemistry as a Lewis acid catalyst. The electronics industry uses boron tribromide as a boron source in pre-deposition processes for doping in the manufacture of semiconductors.[6] Boron tribromide also mediates the dealkylation of aryl alkyl ethers, for example demethylation of 3,4-dimethoxystyrene into 3,4-dihydroxystyrene. SynthesisThe reaction of boron carbide with bromine at temperatures above 300 °C leads to the formation of boron tribromide. The product can be purified by vacuum distillation. HistoryThe first synthesis was done by M. Poggiale in 1846 by reacting boron trioxide with carbon and bromine at high temperatures:[7] B2O3 + 3 C + 3 Br2 → 2 BBr3 + 3 CO An improvement of this method was developed by F. Wöhler and Deville in 1857. By starting from amorphous boron the reaction temperatures are lower and no carbon monoxide is produced:[8] 2 B + 3 Br2 → 2 BBr3 ApplicationsBoron tribromide is used in organic synthesis,[9] pharmaceutical manufacturing, image processing, semiconductor doping, semiconductor plasma etching, and photovoltaic manufacturing. See also
References1. ^1 2 3 4 5 {{PGCH|0061}} 2. ^{{ cite web | publisher = National Institute for Occupational Safety and Health | url = https://www.cdc.gov/niosh/pel88/10294-33.html | work = Toxicologic Review of Selected Chemicals | title = Boron Tribromide | date = 2018-09-21 }} 3. ^{{ cite journal | title = Boron Tribromide | author = Doyagüez, E. G. | journal = Synlett | year = 2005 | volume = 2005 | issue = 10 | pages = 1636–1637 | doi = 10.1055/s-2005-868513 | url = http://www.thieme-connect.de/ejournals/pdf/synlett/doi/10.1055/s-2005-868513.pdf | format = pdf | access-date = 2012-05-16 | archive-url = https://web.archive.org/web/20141207084249/https://www.thieme-connect.de/ejournals/pdf/synlett/doi/10.1055/s-2005-868513.pdf# | archive-date = 2014-12-07 | dead-url = yes | df = }} 4. ^{{ cite journal | title = BBr3-Assisted Cleavage of Most Ethers Does Not Follow the Commonly Assumed Mechanism |author1=Sousa, C. |author2=Silva, P.J |lastauthoramp=yes | journal = Eur. J. Org. Chem. | year = 2013 | volume = 2013| issue = 23 | pages = 5195–5199| doi = 10.1002/ejoc.201300337 }} 5. ^{{ cite journal | title = Demethylation of Aryl Methyl Ethers by Boron Tribromide |author1=McOmie, J. F. W. |author2=Watts, M. L. |author3=West, D. E. | journal = Tetrahedron | year = 1968 | volume = 24 | issue = 5 | pages = 2289–2292 | doi = 10.1016/0040-4020(68)88130-X }} 6. ^{{ cite journal |author1=Komatsu, Y. |author2=Mihailetchi, V. D. |author3=Geerligs, L. J. |author4=van Dijk, B. |author5=Rem, J. B. |author6=Harris, M. | title = Homogeneous p+ emitter diffused using borontribromide for record 16.4% screen-printed large area n-type mc-Si solar cell | journal = Solar Energy Materials and Solar Cells | year = 2009 | volume = 93 | issue = 6–7 | pages = 750–752 | doi = 10.1016/j.solmat.2008.09.019 }} 7. ^{{ cite journal | title = Nouveau composé de brome et de bore, ou acide bromoborique et bromoborate d'ammoniaque | author = Poggiale, M. | journal = Comptes Rendus Hebdomadaires des Séances de l'Académie des Sciences | volume = 22 | pages = 124–130 | year = 1846 | url = http://gallica.bnf.fr/ark:/12148/bpt6k29798/f128.table }} 8. ^{{ cite journal | title = Du Bore | author1 = Wöhler, F. | authorlink1 = Friedrich Wöhler | author2 = Deville, H. E. S.-C. | authorlink2 = Henri Etienne Sainte-Claire Deville | journal = Annales de Chimie et de Physique | volume = 52 | issue = | pages = 63–92 | year = 1858 | url = http://gallica.bnf.fr/ark:/12148/bpt6k347939/f62.table }} 9. ^{{cite book | title = Boron Tribromide | author = Akira Suzuki, Shoji Hara, Xianhai Huang | doi = 10.1002/047084289X.rb244.pub2 | journal = E-EROS Encyclopedia of Reagents for Organic Synthesis| year = 2006 | isbn = 978-0471936237 }} Further reading
External links
4 : Boron compounds|Bromides|Boron halides|Acid catalysts |
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