| Revision as of 19:28, 4 May 2010 editA876 (talk | contribs)Extended confirmed users10,121 editsm →related compounds: added Tetraphenylphosphonium chloride← Previous edit |
Latest revision as of 00:41, 8 June 2023 edit undoPlantman (talk | contribs)Extended confirmed users811 edits // Edit via WikiplusTags: Mobile edit Mobile web edit Advanced mobile edit |
| (26 intermediate revisions by 18 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| Name = Triphenylphosphine dichloride |
|
|
|
| Watchedfields = changed |
| ⚫ |
| ImageFile = Dichlorotriphenylphosphine-2D.png |
|
|
|
| verifiedrevid = 430032953 |
|
| ImageSize = 150px |
|
|
⚫ |
| Name = Triphenylphosphine dichloride |
| ⚫ |
| ImageName = Structural formula |
|
|
| ImageFileL1 = Dichlorotriphenylphosphine-molecular-from-xtal-1998-3D-balls.png |
|
| ImageFile = Dichlorotriphenylphosphine-2D.png |
|
| ImageSizeL1 = 150px |
|
| ImageSize = 150px |
|
⚫ |
| ImageName = Structural formula |
| ⚫ |
| ImageNameL1 = Ball-and-stick model |
|
|
| ImageFileR1 = Dichlorotriphenylphosphine-molecular-from-xtal-1998-3D-vdW.png |
|
| ImageFileL1 = Dichlorotriphenylphosphine-molecular-from-xtal-1998-3D-balls.png |
|
⚫ |
| ImageNameL1 = Ball-and-stick model |
|
| ImageSizeR1 = 150px |
|
|
⚫ |
| ImageFileR1 = Dichlorotriphenylphosphine-molecular-from-xtal-1998-3D-vdW.png |
|
| ImageNameR1 = Space-filling model |
|
| ImageNameR1 = Space-filling model |
|
| IUPACName = Dichlorotriphenyl-λ<sup>5</sup>-phosphane |
|
| PIN = Dichlorotri(phenyl)-λ<sup>5</sup>-phosphane |
|
| OtherNames =Dichlorotriphenylphosphorane |
|
| OtherNames =Dichlorotriphenylphosphorane |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| CASNo = 2526-64-9 |
|
|
| RTECS = |
|
| CASNo = 2526-64-9 |
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
| ⚫ |
}} |
|
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| Section2 = {{Chembox Properties |
|
|
|
|
| ⚫ |
| Formula = C<sub>18</sub>H<sub>15</sub>Cl<sub>2</sub>P |
|
|
|
| UNII = 6CL2293LZ3 |
| ⚫ |
| MolarMass = 333.19 g/mol |
|
|
| Appearance = |
|
| PubChem = 260420 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
| Density = |
|
|
| Solubility = |
|
| ChemSpiderID = 228579 |
|
|
| SMILES = ClP(Cl)(c1ccccc1)(c1ccccc1)c1ccccc1 |
| ⚫ |
| MeltingPt = 176 °C<ref name="Grignard">{{ cite journal | author = ], J. Savard | journal = ] | year = 1931 | volume = 192 | pages = 592–5 }}</ref>, 85-100 °C<ref name="e-EROS">], {{doi|10.1002/047084289X.rt371}}</ref> |
|
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
|
| BoilingPt = |
|
|
|
| StdInChI = 1S/C18H15Cl2P/c19-21(20,16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H |
|
| RefractIndex = |
|
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
| ⚫ |
}} |
|
|
|
| StdInChIKey = ASWXNYNXAOQCCD-UHFFFAOYSA-N |
|
| Section3 = {{Chembox Structure |
|
|
⚫ |
}} |
|
| MolShape = |
|
|
⚫ |
|Section2={{Chembox Properties |
|
| Dipole = |
|
|
⚫ |
| Formula = C<sub>18</sub>H<sub>15</sub>Cl<sub>2</sub>P |
|
}} |
|
|
⚫ |
| MolarMass = 333.19 g/mol |
|
| Section7 = {{Chembox Hazards |
|
|
|
| Solubility = Reacts |
|
| ExternalMSDS = |
|
|
| EUClass = |
|
| MeltingPtC = 176 |
|
⚫ |
| MeltingPt_ref = <ref name="Grignard">{{cite journal | author = ], J. Savard | journal = ] | year = 1931 | volume = 192 | pages = 592–5}}</ref> 85-100 °C<ref name="e-EROS">], {{doi|10.1002/047084289X.rt371}}</ref> |
|
| FlashPt = |
|
|
⚫ |
}} |
|
| RPhrases = |
|
|
⚫ |
|Section8={{Chembox Related |
|
| SPhrases = |
|
|
⚫ |
| OtherCompounds = ]s<br/>]<br/>]<br/>]<br/>]<br/>] |
|
| RSPhrases = |
|
|
}} |
|
}} |
| ⚫ |
| Section8 = {{Chembox Related |
|
|
| Function = |
|
|
| OtherFunctn = |
|
| ⚫ |
| OtherCpds = ]s<br/>]<br/>]<br/>]<br/>]<br/>] |
|
|
}} |
|
|
}} |
|
}} |
|
|
|
|
|
'''Triphenylphosphine dichloride''', Ph<sub>3</sub>PCl<sub>2</sub>, is a ] widely used in organic chemistry. Applications include the conversion of ]s and ]s to ]s, the cleavage of ]s to vicinal dichlorides and the chlorination of ]s to ]s.<ref name="e-EROS" /> |
|
'''Triphenylphosphine dichloride''', (C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>PCl<sub>2</sub>, is a ] widely used in organic chemistry. Applications include the conversion of ]s and ]s to ]s, the cleavage of ]s to vicinal dichlorides and the chlorination of ]s to ]s.<ref name="e-EROS" /> |
|
|
|
|
|
== Structure == |
|
== Structure == |
|
In ] solvents such as ] or ] solutions, Ph<sub>3</sub>PCl<sub>2</sub> adopts an ionic ] structure, Cl<sup>−</sup>,<ref name="Godfrey 1996">{{ cite journal | journal = ] | year = 1996 | pages = 2521−2522 | doi = 10.1039/CC9960002521 | author = S. M. Godfrey, C. A. McAuliffe, R. G. Pritchard, J. M. Sheffield | title = An X-ray crystallorgraphic study of the reagent Ph3PCl2; not charge-transfer, R3P–Cl–Cl, trigonal bipyramidal or Cl but an unusual dinuclear ionic species, Cl containing long Cl–Cl contacts }}</ref> whereas in non-polar solvents like ] it exists as a non-solvated ] molecule.<ref name="Godfrey 1998">{{ cite journal | journal = Chem. Commun. | year = 1998 | pages = 921−922 | doi = 10.1039/a800820e | author = S. M. Godfrey, C. A. McAuliffe, J. M. Sheffield | title = Structural dependence of the reagent Ph3PCl2 on the nature of the solvent, both in the solid state and in solution; X-ray crystal structure of trigonal bipyramidal Ph3PCl2, the first structurally characterised five-coordinate R3PCl2 compound }}</ref> Two species can also adopt an unusual dinuclear ionic structure—both interacting with a Cl<sup>−</sup> via long Cl–Cl contacts.<ref name="Godfrey 1996"/> |
|
In ]s such as ], Ph<sub>3</sub>PCl<sub>2</sub> adopts an ionic ] structure, Cl<sup>−</sup>,<ref name="Godfrey 1996">{{cite journal | journal = ] | year = 1996 | pages = 2521–2522 | doi = 10.1039/CC9960002521 |author1=S. M. Godfrey |author2=C. A. McAuliffe |author3=R. G. Pritchard |author4=J. M. Sheffield | title = An X-ray crystallorgraphic study of the reagent Ph3PCl2; not charge-transfer, R3P–Cl–Cl, trigonal bipyramidal or Cl but an unusual dinuclear ionic species, Cl containing long Cl–Cl contacts | issue = 22}}</ref> whereas in non-polar solvents like ] it exists as a non-solvated ] molecule.<ref>{{cite journal | journal = Chem. Commun. | year = 1998 | pages = 921–922 | doi = 10.1039/a800820e |author1=S. M. Godfrey |author2=C. A. McAuliffe |author3=J. M. Sheffield | title = Structural dependence of the reagent Ph3PCl2 on the nature of the solvent, both in the solid state and in solution; X-ray crystal structure of trigonal bipyramidal Ph3PCl2, the first structurally characterised five-coordinate R3PCl2 compound | issue = 8}}</ref> Two species can also adopt an unusual dinuclear ionic structure—both interacting with a Cl<sup>−</sup> via long Cl–Cl contacts.<ref name="Godfrey 1996"/> |
|
|
|
|
|
<gallery> |
|
<gallery> |
| Line 62: |
Line 57: |
|
|
|
|
|
Both reagents are typically used in solution to ensure the correct ].<ref name="e-EROS" /> |
|
Both reagents are typically used in solution to ensure the correct ].<ref name="e-EROS" /> |
|
|
|
|
|
Ph<sub>3</sub>PCl<sub>2</sub> can also be obtained by the reaction of iodobenzene dichloride (PhICl<sub>2</sub>) and triphenylphosphine.<ref>Carle, M. S., Shimokura, G. K. and Murphy, G. K. (2016), Iodobenzene Dichloride in the Esterification and Amidation of Carboxylic Acids: In-Situ Synthesis of Ph3PCl2. ], 2016: 3930–3933. {{DOI:10.1002/ejoc.201600714}}</ref> |
|
|
|
|
|
Alternatively, Ph<sub>3</sub>PCl<sub>2</sub> can be obtained by chlorination of ] with, for example, ], as in Grignard's original 1931 synthesis.<ref name="Grignard" /> |
|
Alternatively, Ph<sub>3</sub>PCl<sub>2</sub> can be obtained by chlorination of ] with, for example, ], as in Grignard's original 1931 synthesis.<ref name="Grignard" /> |
| Line 69: |
Line 66: |
|
|
|
|
|
] |
|
] |
|
|
] |
|
|
] |