| Revision as of 14:21, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 467859124 of page Triphenyl_phosphite for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 02:29, 19 June 2024 edit Vycl1994 (talk | contribs)Autopatrolled, Extended confirmed users125,726 editsNo edit summary |
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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 = 407450386 |
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| verifiedrevid = 470616535 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = P(OPh)3.png |
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| ImageFile = P(OPh)3.png |
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| ImageFile1 = Triphenyl-phosphite-from-xtal-3D-bs-17.png |
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| ImageSize = 200px |
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| ImageFile1 = TriphenylPhosphite_3D_BallStick.png |
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| ImageSize1 = 250px |
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| ImageSize1 = 250px |
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| IUPACName = Triphenyl phosphite |
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| PIN = Triphenyl phosphite |
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|Section1={{Chembox Identifiers |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7259 |
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| ChemSpiderID = 7259 |
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| StdInChIKey = HVLLSGMXQDNUAL-UHFFFAOYSA-N |
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| StdInChIKey = HVLLSGMXQDNUAL-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 101-02-0 |
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| CASNo = 101-02-0 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 9P45GRD24X |
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| PubChem = 7540 |
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| PubChem = 7540 |
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| SMILES = O(P(Oc1ccccc1)Oc2ccccc2)c3ccccc3 |
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| SMILES = O(P(Oc1ccccc1)Oc2ccccc2)c3ccccc3 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>18</sub>H<sub>15</sub>O<sub>3</sub>P |
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| Formula = C<sub>18</sub>H<sub>15</sub>O<sub>3</sub>P |
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| MolarMass = 310.28 g/mol |
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| MolarMass = 310.28 g/mol |
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| Appearance = colourless liquid |
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| Appearance = colourless liquid |
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| Density = 1.184 g/mL |
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| Density = 1.184 g/mL |
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| MeltingPt = 22–24 °C |
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| MeltingPtC = 22 to 24 |
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| BoilingPt = 360 °C |
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| BoilingPtC = 360 |
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| Solubility = organic solvents |
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| Solubility = low |
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| SolubleOther = organic solvents |
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| MagSus = -183.7·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section3 = {{Chembox Hazards |
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| MainHazards = flammable |
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| MainHazards = flammable |
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| FlashPt = |
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| Autoignition = |
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'''Triphenyl phosphite''' is the ] with the ] P(OC<sub>6</sub>H<sub>5</sub>)<sub>3</sub>. It is a colourless viscous liquid. |
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==Preparation== |
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Triphenylphosphite is prepared from ] and ] in the presence of a catalytic amount of base: |
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:PCl<sub>3</sub> + 3 HOC<sub>6</sub>H<sub>5</sub> → P(OC<sub>6</sub>H<sub>5</sub>)<sub>3</sub> + 3 HCl |
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==Reactions== |
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Triphenylphosphite is a precursor to ], it serves as a source of P<sup>3+</sup> that is less electrophilic than phosphorus trichloride:<ref>{{cite book | series = ] |author1=Leutkens, M. L. Jr. |author2=Sattelberger, A. P. |author3=Murray, H. H. |author4=Basil, J. D. |author5-link=John P. Fackler Jr. |author5=Fackler, J. P. Jr. |chapter=Trimethylphosphine | year = 1990 | title = Inorganic Syntheses | volume = 28 | pages = 305–310 | doi = 10.1002/9780470132593.ch76|isbn=978-0-470-13259-3 }}</ref> |
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: (C<sub>6</sub>H<sub>5</sub>O)<sub>3</sub>P + 3{{nbsp}}CH<sub>3</sub>MgBr → P(CH<sub>3</sub>)<sub>3</sub> + 3{{nbsp}}"MgBrOC<sub>6</sub>H<sub>5</sub>" |
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Triphenylphosphite is quaternized by ]:<ref>{{cite journal |author=H. N. Rydon|doi=10.15227/orgsyn.051.0044|title=Alkyl Iodides: Neopentyl Iodide and Iodocyclohexane|journal=Organic Syntheses|year=1971|volume=51|page=44}}</ref> |
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: (C<sub>6</sub>H<sub>5</sub>O)<sub>3</sub>P + CH<sub>3</sub>I → <sup>+</sup>I<sup>−</sup> |
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===Coordination complexes=== |
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Triphenylphosphite is a common ] in ]. It forms zero-valent complexes of the type M<sub>4</sub> (M = Ni, Pd, Pt). The nickel complex can be prepared by displacement of the diene from ]:<ref>{{cite book|doi=10.1002/9780470132487.ch34|chapter=Olefin, Acetylene, Phosphine, Isocyanide, and Diazene Complexes of Nickel(0)|year=1977|last1=Ittel|first1=Steven D.|title=Inorganic Syntheses|pages=117–124|volume=XVII|isbn=978-0-470-13248-7}}</ref> |
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: Ni(COD)<sub>2</sub> + 4 P(OC<sub>6</sub>H<sub>5</sub>)<sub>3</sub> → Ni<sub>4</sub> + 2 COD |
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Related complexes are ]s for the ] of ]s. It also forms a variety of Fe(0) and Fe(II) complexes such as the di] H<sub>2</sub>Fe<sub>4</sub>.<ref>{{cite journal|doi=10.1021/ja00768a022|title=Stereochemically Nonrigid Six-Coordinate Molecules. II. Preparations and Reactions of Tetrakis(organophosphorus)metal Dihydride Complexes|year=1972|last1=Gerlach|first1=D. H.|last2=Peet|first2=W. G.|last3=Muetterties|first3=E. L.|journal=Journal of the American Chemical Society|volume=94|pages=4545|issue=13}}</ref> |
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==Polyamorphism== |
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Triphenylphosphite is a notable example of ] in organic compounds, namely it exists in two different amorphous forms at temperatures about 200 K.<ref>{{cite journal|doi=10.1021/jp9530820|title=Supercooled Liquids and Polyamorphism†|year=1996|last1=Ha|first1=Alice|last2=Cohen|first2=Itai|last3=Zhao|first3=Xiaolin|last4=Lee|first4=Michelle|last5=Kivelson|first5=Daniel|journal=The Journal of Physical Chemistry|volume=100|pages=1–4}}</ref> One polymorphic modification of triphenyl phosphite was obtained by means of crystallization in ]s.<ref>D.G. Golovanov, K.A. Lyssenko, M.Yu. Antipin, Ya.S. Vygodskii, E.I. Lozinskaya, A.S. Shaplov. ”Long-awaited polymorphic modification of triphenyl phosphite“, Cryst. Eng. Comm., 2005, v. 7, no. 77, P.465 – 468. </ref> |
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==References== |
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{{reflist}} |
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] |
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] |