| Revision as of 13:05, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 467495684 of page Thionyl_bromide for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 17:17, 13 November 2024 edit Bernanke's Crossbow (talk | contribs)Extended confirmed users7,873 edits →top: make proper lede |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 432182889 |
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| Watchedfields = changed |
| ⚫ |
| Name = Thionyl bromide |
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| verifiedrevid = 470607318 |
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| ImageFileL1 = Thionyl-bromide.png |
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| Name = Thionyl bromide |
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| ImageSizeL1 = 120px |
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| ImageNameL1 = Structure of the thionyl bromide molecule |
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| ImageFileL1 = Thionyl-bromide.png |
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| ImageNameL1 = Structure of the thionyl bromide molecule |
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| ImageFileR1 = Thionyl-bromide-from-xtal-3D-balls-B.png |
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| ImageFileR1 = Thionyl-bromide-from-xtal-3D-vdW-B.png |
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| ImageNameR1 = 3D model of a thionyl bromide molecule |
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| ImageSizeR1 = 120px |
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| ImageFile2 =Thionyl-bromide-xtal-3D-vdW.png |
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| ImageNameR1 = 3D model of a thionyl bromide molecule |
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| ImageName2 = Molecular arrangement in solid SOBr<sub>2</sub> (note that this is dramatically different from the crystal structure of its chloride analogue) |
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| IUPACName = Thionyl bromide |
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| IUPACName = Thionyl bromide |
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| OtherNames = Sulfur oxy dibromide |
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| OtherNames = Sulfur oxy dibromide |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| SMILES = BrS(Br)=O |
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| SMILES = BrS(Br)=O |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 61483 |
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| ChemSpiderID = 61483 |
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| EC_number = 208-064-3 |
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| PubChem = 68176 |
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| PubChem = 68176 |
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| InChI = 1/Br2OS/c1-4(2)3 |
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| InChI = 1/Br2OS/c1-4(2)3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = HFRXJVQOXRXOPP-UHFFFAOYSA-N |
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| StdInChIKey = HFRXJVQOXRXOPP-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 507-16-4 --> |
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| CASNo = 507-16-4 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| RTECS = |
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| UNII = N6CU78B13T |
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| RTECS = |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = SOBr<sub>2</sub> |
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| Formula = SOBr<sub>2</sub> |
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| MolarMass = 207.87 g/mol |
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| MolarMass = 207.87 g/mol |
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| Appearance = colorless liquid |
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| Appearance = colorless liquid |
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| Density = 2.688 g/mL, liquid |
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| Density = 2.688 g/mL, liquid<ref name=Sulf/> |
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| Solubility = decomposes violently |
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| Solubility = decomposes |
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| SolubleOther = reacts in ], acetone, and alcohol<br />soluble in benzene, toluene, ether |
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| MeltingPt = –52 °C |
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| MeltingPtC = -52 |
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| BoilingPt = 68 °C/40 mmHg |
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| MeltingPt_notes = ; may include ]<ref name=Sulf>{{cite book|title=Sulfur in Organic and Inorganic Chemistry|volume=1|editor-first=Alexander|editor-last=Senning|year=1971|publisher=Marcel Dekker|location=New York|lccn=70-154612|isbn=0-8247-1615-9|first=Philip S.|last=Magee|chapter=The Sulfur–Bromine Bond|pages=271–276}}</ref> |
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| Viscosity = |
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| BoilingPt = {{ubl|48 °C at 20 mmHg<ref name=Sulf/>|136 °C at 1 atm but {{frac|1|3}} decomposes<ref name=Sulf/>}} |
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| Viscosity = |
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}} |
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}} |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| MolShape = trigonal pyramidal |
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| MolShape = trigonal pyramidal |
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| Dipole = 1.47 D<ref name=Sulf/> |
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| Dipole = |
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}} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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| ExternalMSDS = |
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| MainHazards = dangerously sensitive to water<br />source of bromine, HBr |
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| MainHazards = Readily decomposes in air to toxic gases |
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| FlashPt = nonflammable |
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| FlashPt = Non-flammable |
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| Hazards_ref = <ref>{{cite web |title=Thionyl bromide |url=https://www.sigmaaldrich.com/AU/en/product/ALDRICH/251259 |publisher=Sigma Aldrich}}</ref> |
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| RPhrases = 14-20/21-34 |
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| GHSPictograms = {{GHS05}}{{GHS07}} |
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| SPhrases = 26-36/37/39-45 |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|312|314|332}} |
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| PPhrases = {{P-phrases|280|305+351+338|310}} |
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}} |
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}} |
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| Section8 = {{Chembox Other |
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|Section8={{Chembox Related |
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| OtherCpds =], ]; |
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| OtherCompounds =], ]; |
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PBr<sub>3</sub>, Br<sub>2</sub>}} |
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], ]}} |
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}} |
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}} |
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'''Thionyl bromide''' is the chemical compound SOBr<sub>2</sub>. It is less stable and less widely used than its ] analogue, ], but engages in similar reactions.<ref>{{ cite encyclopedia | author = Mundy, B. P. | title = Thionyl Bromide | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | editor = Paquette, E. | year = 2004 | publisher = J. Wiley & Sons | location = New York | doi = 10.1002/047084289X.rt098 | isbn = 0471936235 }}</ref> |
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==Chemistry== |
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It is prepared by the action of ] on thionyl chloride,<ref>{{cite book | last=Booth | first=Harold Simmons | title=Inorganic syntheses. Volume 1 | publication-place=New York | date=1939 | isbn=978-0-470-13264-7 | oclc=86223179 |page=113}}</ref> although the corresponding reaction at higher pH (i.e. alkali bromides) proceeds only with difficulty:<ref name=Sulf/> |
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:SOCl<sub>2</sub> + 2 HBr → SOBr<sub>2</sub> + 2 HCl |
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] (but not ]!) converts ] to thionyl bromide. Thionyl chlorobromide appears to be a key intermediate in these syntheses, but has not been isolated.<ref name=Sulf/> |
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Thionyl bromide will convert ]s to alkyl bromides and carboxylic acids to acyl bromides. Unlike with thionyl chloride, stoichiometric bases are problematic activating agents, because free bromide anions decompose thionyl bromide to ], ], and ].<ref name=Sulf/> |
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It can be used for brominations of certain α,β-unsaturated carbonyl compounds.<ref>{{cite journal |last1=Saraf |first1=S. D. |title=Reaction of thionyl bromide with tropolone and phenol |journal=Canadian Journal of Chemistry |date=1 August 1969 |volume=47 |issue=15 |pages=2803–2804 |doi=10.1139/v69-465|doi-access=free }}</ref> |
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It may occasionally be used as a solvent.<ref>{{cite journal |last1=Furlani |first1=C. |last2=Zinato |first2=E. |title=Hexahalogenoniobates(V), Oxopentahalogenoniobates(V) and their electronic spectra |journal=Zeitschrift für anorganische und allgemeine Chemie |date=May 1967 |volume=351 |issue=3–4 |pages=210–218 |doi=10.1002/zaac.19673510311}}</ref><ref>{{cite book |title=The chemistry of the actinide and transactinide elements. Volumes 1-6 |date=2010 |publisher=Springer |location=Dordrecht |isbn=978-94-007-0211-0 |page=526 |edition=4th}}</ref> |
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==Safety== |
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SOBr<sub>2</sub> hydrolyzes readily in air to release dangerous fumes of ] and ]. |
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:SOBr<sub>2</sub> + H<sub>2</sub>O → SO<sub>2</sub> + 2 HBr |
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Decomposition to ] and ] does not occur except at elevated temparatures.<ref name=Sulf/> |
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==References== |
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{{reflist}} |
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{{commonscat|Thionyl bromide}} |
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{{sulfur compounds}} |
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] |
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] |
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] |
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] |
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] |
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{{inorganic-compound-stub}} |