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{{chembox |
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{{Chembox |
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| verifiedrevid = 408397902 |
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| verifiedrevid = 462789464 |
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| Name = Benzeneselenol |
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| ImageFileL1 = Benzeneselenol-2D-skeletal.png |
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| Name = Benzeneselenol |
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| ImageFileL1 = Benzeneselenol-2D-skeletal.png |
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| ImageFileR1 = Benzeneselenol-3D-vdW.png |
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| ImageSizeL1 = 100 px |
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| ImageFileR1 = Benzeneselenol-3D-vdW.png |
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| IUPACName = Benzeneselenol |
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| OtherNames = {{ubl|Phenylselenol|Selenaphenol|Selenophenol}} |
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| ImageSizeR1 = 125 px |
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|Section1={{Chembox Identifiers |
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| IUPACName = benzeneselenol |
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| PubChem = 69530 |
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| OtherNames = Selenaphenol,<br />selenophenol,<br />phenylselenol |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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| PubChem = 69530 |
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| ChemSpiderID = 62734 |
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| SMILES = c1ccccc1 |
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| ChemSpiderID = 62734 |
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| InChI = 1/C6H6Se/c7-6-4-2-1-3-5-6/h1-5,7H |
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| SMILES = c1ccccc1 |
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| InChIKey = WDODWFPDZYSKIA-UHFFFAOYAD |
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| InChI = 1/C6H6Se/c7-6-4-2-1-3-5-6/h1-5,7H |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = WDODWFPDZYSKIA-UHFFFAOYAD |
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| StdInChI = 1S/C6H6Se/c7-6-4-2-1-3-5-6/h1-5,7H |
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| StdInChI = 1S/C6H6Se/c7-6-4-2-1-3-5-6/h1-5,7H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WDODWFPDZYSKIA-UHFFFAOYSA-N |
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| StdInChIKey = WDODWFPDZYSKIA-UHFFFAOYSA-N |
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| CASNo = 645-96-5 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| RTECS = |
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| CASNo = 645-96-5 |
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}} |
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| EINECS = 211-457-2 |
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| Section2 = {{Chembox Properties |
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| RTECS = |
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| Formula = C<sub>6</sub>H<sub>6</sub>Se |
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}} |
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| MolarMass = 157.07 g/mol |
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|Section2={{Chembox Properties |
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| Appearance = colourless liquid |
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| Formula = {{chem2|C6H5SeH}} |
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| Density = 1.479 g/cm<sup>3</sup> |
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| C=6|H=6|Se=1 |
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| Solubility = slightly |
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| Appearance = colorless liquid |
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| Solvent = other solvents |
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| Odor = extremely foul yet characteristic |
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| SolubleOther = most organic solvents |
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| Density = 1.479 g/cm<sup>3</sup> |
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| MeltingPt = |
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| Solubility = slightly |
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| BoilingPt = 71-72 °C (18 mm Hg) |
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| Solvent = other solvents |
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| Viscosity = |
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| SolubleOther = most organic solvents |
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| RefractIndex = 1.616 |
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| MeltingPt = |
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}} |
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| BoilingPtC = 71 to 72 |
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| Section3 = {{Chembox Structure |
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| BoilingPt_notes = (18 ]) |
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| Coordination = |
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| Viscosity = |
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| CrystalStruct = |
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| Dipole = 1.1 ] |
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| RefractIndex = 1.616 |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section3={{Chembox Structure |
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| Coordination = |
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| ExternalMSDS = |
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| CrystalStruct = |
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| MainHazards = toxic |
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| Dipole = 1.1 ] |
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| FlashPt = |
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}} |
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| RPhrases = 23/25-33-50/53 |
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|Section7={{Chembox Hazards |
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| SPhrases = 20/21-28-45-60-61 |
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| ExternalSDS = |
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}} |
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| MainHazards = toxic |
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| Section8 = {{Chembox Related |
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| FlashPt = |
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| OtherCpds = ],<br />],<br />] |
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| GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}} |
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}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|331|373|410}} |
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| PPhrases = {{P-phrases|}} |
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}} |
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|Section8={{Chembox Related |
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| OtherCompounds = {{ubl|]|]|]|]}} |
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}} |
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'''Benzeneselenol''' is the ] with the formula C<sub>6</sub>H<sub>5</sub>SeH, often abbreviated ]SeH. This intensely malodorous liquid is a useful reagent in ]. |
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'''Benzeneselenol''', also known as '''selenophenol''', is the ] with the ] {{chem2|C6H5SeH|auto=1}}, often abbreviated ]SeH. It is the ] analog of ]. This colourless, malodorous compound is a ] in ].<ref name=eEROS/> |
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==Synthesis and basic properties== |
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==Synthesis== |
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PhSeH is prepared via the reaction of ] and ]:<ref>{{OrgSynth | author = Foster, D. G. | title = Selenophenol | collvol = 3 | collvolpages = 771 | year = 1955 | prep = cv3p0771}}</ref> |
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Benzeneselenol is prepared by the reaction of ] and ]:<ref>{{cite journal| last1=Foster|first1=D. G.|title= Selenophenol|year=1944|volume=24|pages=89|doi = 10.15227/orgsyn.024.0089|journal=Organic Syntheses}}</ref> |
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:PhMgBr + Se → PhSeMgBr |
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:PhSeMgBr + HCl → PhSeH + MgBrCl |
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Since benzeneselenol does not have a long shelf life, it is often generated in situ. A common method is by reduction of ]. A further reason for this conversion is that often, it is the anion that is sought.<ref name=eEROS/> |
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:] |
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==Reactions== |
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More so than thiophenol, benzeneselenol is easily oxidized by air to give ]. An idealized equation for this reaction is: |
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More so than thiophenol, benzeneselenol is easily oxidized by air. The facility of this reaction reflects the weakness of the Se-H bond, ] of which is estimated to be between 67 and 74 kcal/mol.<ref name=eEROS/> In contrast, the S-H BDE for thiophenol is near 80 kcal/mol.<ref>{{cite journal |doi=10.1021/jp035622w|title=The S−H Bond Dissociation Enthalpies and Acidities of Para and Meta Substituted Thiophenols: A Quantum Chemical Study |year=2003 |last1=Chandra |first1=Asit K. |last2=Nam |first2=Pham-Cam |last3=Nguyen |first3=Minh Tho |journal=The Journal of Physical Chemistry A |volume=107 |issue=43 |pages=9182–9188 |bibcode=2003JPCA..107.9182C}}</ref> The product is ] as shown in this idealized equation: |
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: 2 PhSeH + O → PhSeSePh + H<sub>2</sub>O |
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:{{chem2|4 PhSeH + O2 -> 2 PhSeSePh + 2 H2O}} |
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The presence of the ] is signaled by a yellow coloration in most samples of PhSeH. The diselenide can be converted back to the selenol by reduction followed by acidification of the resulting PhSe<sup>−</sup>. |
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The presence of the ] in benzeneselenol is indicated by a yellow coloration. The diselenide can be converted back to the selenol by reduction followed by acidification of the resulting {{chem2|PhSe−}}. |
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PhSeH is acidic with a ] of 5.9. Thus at neutral ], it is mostly ionized: |
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PhSeH is approximately seven times more acidic than the related ]. Both compounds dissolve in water upon the addition of base. |
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:{{chem2|PhSeH → PhSe− + H+}} |
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PhSeH is renowned in ] as the precursor to its conjugate base PhSe<sup>−</sup>, a potent ].<ref>Sonoda, N.; Ogawa, A.; Recupero, F. "Benzeneselenol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.</ref> |
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It is approximately seven times more acidic than the related ]. Both compounds dissolve in water upon the addition of base. The conjugate base is {{chem2|PhSe−}}, a potent ].<ref name=eEROS>{{Cite book |doi = 10.1002/047084289X.rb018.pub2 |chapter = Benzeneselenol |title = Encyclopedia of Reagents for Organic Synthesis |year = 2005 |last1 = Sonoda |first1 = Noboru |last2 = Ogawa |first2 = Akiya |last3 = Recupero |first3 = Francesco |isbn = 0471936235}}</ref> |
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==History== |
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==History== |
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Benzeneselenol was first prepared by the reaction of ] with ] in the presence of ].<ref>Chabrié, M. Camille “Premiers essays de synthèse de composés organiques séléniés dans la série aromatique” Bull. soc. chim. France, 50, 133 (1888); Ann. chim. phys., (6) 20, 229 (1890)</ref> |
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Benzeneselenol was first reported in 1888 by the reaction of ] with ] ({{chem2|SeCl4}}) in the presence of ] ({{chem2|AlCl3}}).<ref>{{cite journal | author = Chabrié, M. C. | title = Premiers essais de synthèse de composés organiques séléniés dans la série aromatique | journal = ] | year = 1888 | volume = 50 | pages = 133–137 | url = http://gallica.bnf.fr/ark:/12148/bpt6k281999w/f157}}</ref><ref>{{cite journal | author = Chabrié, M. C. | title = Sur la synthèse de quelques composés séléniés dans la série aromatique| journal = ] | year = 1890 | volume = 6 | issue = 20 | pages = 202–286 | url = http://gallica.bnf.fr/ark:/12148/bpt6k34890j/f200}}</ref> |
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==Safety== |
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The compound is intensely malodorous<ref name="pipeline">{{cite web | author = Lowe, D. | url = https://www.science.org/content/blog-post/things-i-won-t-work-selenophenol | work = In the Pipeline | title = Things I wont work with: Selenophenol | date = 2012-05-15}}</ref> and, like other organoselenium compounds, toxic. |
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==References== |
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==References== |
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{{reflist}} |
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<references/> |
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