| Revision as of 16:08, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 437646476 of page 1,2-Bis(dimethylphosphino)ethane for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 12:43, 12 December 2024 edit Rjwilmsi (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers931,939 editsm →Synthesis: brackets in ref fixTag: AWB |
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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 = 399180057 |
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|verifiedrevid = 477203110 |
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| Name = 1,2-Bis(dimethylphosphino)ethane |
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| OtherNames = DMPE<br>ethylenebis(dimethylphosphine)<br>1,2-Bis(dimethylphosphino)ethane |
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|Name = 1,2-Bis(dimethylphosphino)ethane |
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| ImageFile = dmpe-2D-skeletal-B.png |
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|ImageFile = dmpe-2D-skeletal-B.png |
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|ImageFile1 = Dmpe-from-xtal-1997-3D-balls.png |
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|PIN = (Ethane-1,2-diyl)bis(dimethylphosphane) |
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| ImageName = |
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|OtherNames = DMPE<br>ethylenebis(dimethylphosphine)<br>1,2-Bis(dimethylphosphino)ethane |
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| ImageFile1 = Dmpe-from-xtal-1997-3D-balls.png |
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|Section1={{Chembox Identifiers |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageName1 = |
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|ChemSpiderID = 124423 |
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| IUPACName = Ethane-1,2-diylbis(dimethylphosphane) |
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| EC_number = 627-450-6 |
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| Section1 = {{Chembox Identifiers |
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|InChI = 1/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|SMILES = P(C)(C)CCP(C)C |
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| ChemSpiderID = 124423 |
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|InChIKey = ZKWQSBFSGZJNFP-UHFFFAOYAN |
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| InChI = 1/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 |
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|PubChem = 141059 |
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| SMILES = P(C)(C)CCP(C)C |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = ZKWQSBFSGZJNFP-UHFFFAOYAN |
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|StdInChI = 1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 |
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| PubChem = 141059 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = ZKWQSBFSGZJNFP-UHFFFAOYSA-N |
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| StdInChI = 1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 |
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|CASNo = 23936-60-9 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey = ZKWQSBFSGZJNFP-UHFFFAOYSA-N |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo = <!-- blanked - oldvalue: 23936-60-9 --> |
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|UNII = 9P3522CZ8T |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=6|H=16|P=2 |
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| Formula = C<sub>6</sub>H<sub>16</sub>P<sub>2 |
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|BoilingPtC = 180 |
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| MolarMass = 150.14 g mol<sup>−1</sup> |
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|BoilingPt_notes = |
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| BoilingPt = 180 °C |
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| Density = 0.9 g/mL at 25 °C |
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|Density = 0.9 g/mL at 25 °C |
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}} |
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| Section4 = {{Chembox Hazards |
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| GHSPictograms = {{GHS02}}{{GHS07}}<ref name="sigma">{{SigmaLink |
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| Productgroup = Aldrich |
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| Productcode = 261939 |
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| Accessdate = may 18th, 2011 |
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}}</ref> |
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| RPhrases = {{H-phrases|225|315|319|335}}<ref name="sigma" /> |
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| SPhrases = {{P-phrases|210|261|305+351+338}}<ref name="sigma" /> |
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| NFPA-H = |
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| FlashPt = |
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|Section7={{Chembox Hazards |
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|GHSPictograms = {{GHS02}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|225|250|315|319|335}} |
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| PPhrases = {{P-phrases|210|222|231|233|240|241|242|243|261|264|264+265|271|280|302+335+334|302+352|303+361+353|304+340|305+351+338|319|321|332+317|337+317|362+364|370+378|403+233|403+235|405|501}} |
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| GHS_ref=<ref name="sigma">{{Sigma-Aldrich|Aldrich| id=261939 |name=1,2-Bis(dimethylphosphino)ethane|accessdate=2013-07-20}}</ref> |
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'''1,2-Bis(dimethylphosphino)ethane''' ('''dmpe''') is a ] in ]. It is a colorless, air-sensitive liquid that is soluble in organic solvents. With the formula (CH{{sub|2}}PMe{{sub|2}}){{sub|2}}, dmpe is used as a compact strongly basic ] (Me = ]), Representative complexes include V(dmpe){{sub|2}}(BH{{sub|4}}){{sub|2}}, Mn(dmpe){{sub|2}}(AlH{{sub|4}}){{sub|2}}, Tc(dmpe){{sub|2}}(CO){{sub|2}}Cl, and Ni(dmpe)Cl{{sub|2}}.<ref>{{Greenwood&Earnshaw2nd}}</ref> |
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] |
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==Synthesis== |
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It is synthesised by the reaction of ] with ]:<ref>{{cite journal |author =R. J. Burt |author2 =J. Chatt |author3 =W. Hussain|author4 =G. J. Leigh |title=A convenient synthesis of 1,2-bis(dichlorophosphino)ethane, 1,2-bis(dimethylphosphino)ethane and 1,2-bis(diethylphosphino)ethane |journal=] |volume=182 |issue=2 |year=1979 |pages=203–6 |doi=10.1016/S0022-328X(00)94383-3}}</ref> |
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:Cl{{sub|2}}PCH{{sub|2}}CH{{sub|2}}PCl{{sub|2}} + 4 MeMgI → Me{{sub|2}}PCH{{sub|2}}CH{{sub|2}}PMe{{sub|2}} + 4 MgICl |
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Alternatively it can be generated by alkylation of sodium dimethylphosphide. |
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The synthesis of dmpe from ] has led to serious accidents and has been abandoned.<ref>{{cite book|doi=10.1002/9780470132548.ch42|chapter=Preparation of Tetramethyldiphosphine Disulfide and Ethylenebis(Dimethylphosphine) (Dmpe)|pages=199–200|year=1985|volume=23|last1=Bercaw|first1=J. E.|title=Inorganic Syntheses|last2=Parshall|first2=G. W.|isbn=9780470132548}}</ref> |
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==Related ligands== |
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* ], a bulkier analogue, which is also a solid. |
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* ], more air-stable than dmpe, but less basic. |
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* ], a more rigid analogue of dmpe. |
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* ], the diamine analogue of dmpe. |
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== References == |
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{{reflist}} |
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{{DEFAULTSORT:Bis(dimethylphosphino)ethane, 1, 2-}} |
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] |
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] |
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] |