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Revision as of 11:20, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477103850 of page DIPAMP for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 15:41, 23 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits added Category:2-Methoxyphenyl compounds using HotCat 
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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.}}
{{chembox {{chembox
| Watchedfields = changed | Verifiedfields = changed
| verifiedrevid = 399889137 | verifiedrevid = 477166314
|ImageFile=DIPAMP.png | ImageFile = DIPAMP.png
|ImageSize= | ImageSize =
|ImageFile1=DIPAMP-from-xtal-2004-Mercury-3D-balls.png | ImageFile1 =
|IUPACName=Ethane-1,2-diylbis | PIN = (Ethane-1,2-diyl)bis
|OtherNames= | OtherNames =
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| index1_label = (''R'',''R'')
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| index2_label = (''S'',''S'')
⚫ | ChemSpiderID = 9594634
| index3_label = (''R'',''S'')
⚫ | InChI = 1/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32-/m1/s1
| CASNo = 63589-61-7
⚫ | InChIKey = QKZWXPLBVCKXNQ-ROJLCIKYBJ
| CASNo1 = 55739-58-7
⚫ | InChI1 = 1/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32-/m0/s1
| CASNo2 = 97858-62-3
⚫ | InChIKey1 = QKZWXPLBVCKXNQ-ACHIHNKUBV
⚫ | ChemSpiderID = 2016305
⚫ | SMILES1 = O(c1ccccc1(c2ccccc2)CC(c3ccccc3)c4ccccc4OC)C
| ChemSpiderID1 = 9060243
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| ChemSpiderID2 = 9594634
⚫ | StdInChI = 1S/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32-/m0/s1
| ChemSpiderID3 = 9910039
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | PubChem = 2734557
⚫ | StdInChIKey = QKZWXPLBVCKXNQ-ACHIHNKUSA-N
| PubChem1 = 10884975
| CASNo_Ref = {{cascite|correct|??}}
| PubChem2 = 11419748
| CASNo = <!-- blanked - oldvalue: 55739-58-7 -->
| PubChem3 = 11735331
| CASOther = &nbsp;(''R'',''R'')<br>97858-62-3 (''S'',''S'')
| SMILES = COc1ccccc1P(CCP(c2ccccc2)c3ccccc3OC)c4ccccc4
⚫ | PubChem = 11419748
| SMILES = O(c1ccccc1(c2ccccc2)CC(c3ccccc3)c4ccccc4OC)C | SMILES1 = COc1ccccc1(CC(c2ccccc2)c3ccccc3OC)c4ccccc4
| SMILES2 = COc1ccccc1(CC(c2ccccc2)c3ccccc3OC)c4ccccc4
⚫ }}
⚫ | SMILES3 = O(c1ccccc1(c2ccccc2)CC(c3ccccc3)c4ccccc4OC)C
| Jmol = none
⚫ | StdInChI = 1S/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3
⚫ | StdInChIKey = QKZWXPLBVCKXNQ-UHFFFAOYSA-N
⚫ | InChI1 = 1S/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32-/m1/s1
⚫ | InChIKey1 = QKZWXPLBVCKXNQ-ROJLCIKYSA-N
⚫ | InChI2 = 1S/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32-/m0/s1
⚫ | InChIKey2 = QKZWXPLBVCKXNQ-ACHIHNKUSA-N
| InChI3 = 1S/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32+
| InChIKey3 = QKZWXPLBVCKXNQ-MEKGRNQZSA-N
| UNII1 = BLJ831OWLW
| UNII2 = HS6F5EW3U6
⚫ }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| C=28 | H=28 | O=2 | P=2
| Formula=C<sub>28</sub>H<sub>28</sub>O<sub>2</sub>P<sub>2</sub>
⚫ | Appearance =
| MolarMass=458.47 g/mol
⚫ | Density =
⚫ | Appearance=
⚫ | MeltingPt =
⚫ | Density=
⚫ | BoilingPt =
⚫ | MeltingPt=
⚫ | Solubility =
⚫ | BoilingPt=
⚫ | Solubility=
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards =
| FlashPt= | FlashPt =
| AutoignitionPt =
| Autoignition=
}} }}
}} }}

'''DIPAMP''' is an ] that is used as a ] in ]. It is a white solid that dissolves in organic solvents. Work on this compound by ] was recognized with the ].<ref>{{cite journal|last=Knowles|first=William S.|title=Asymmetric Hydrogenations (Nobel Lecture) Copyright© The Nobel Foundation 2002. We thank the Nobel Foundation, Stockholm, for permission to print this lecture.|journal=Angewandte Chemie International Edition|year=2002|volume=41|issue=12|page=1998|doi=10.1002/1521-3773(20020617)41:12<1998::AID-ANIE1998>3.0.CO;2-8}}</ref> DIPAMP was the basis for one of the first industrial scale ], the synthesis of the drug ].<ref>{{cite journal|last=Vineyard|first=B. D.|author2=Knowles, W. S. |author3=Sabacky, M. J. |author4=Bachman, G. L. |author5= Weinkauff, D. J. |title=Asymmetric hydrogenation. Rhodium chiral bisphosphine catalyst|journal=Journal of the American Chemical Society|year=1977|volume=99|issue=18|pages=5946–5952|doi=10.1021/ja00460a018}}</ref>
:] DIPAMP.]]

DIPAMP is a ] ]. Each ] centre, which is pyramidal, bears three different substituents - ], phenyl, and the ethylene group. The ligand therefore exists as the enantiomeric (''R'',''R'') and (''S'',''S'') pair, as well as the achiral ''meso'' isomer.

DIPAMP was originally prepared by an oxidative coupling, starting from anisyl(phenyl)(methyl)phosphine.

])]<sup>+</sup> by ].<ref>{{cite journal|journal=Tetrahedron: Asymmetry|volume=15|issue=14|author=H.-J.Drexler |author2=Songlin Zhang |author3=Ailing Sun |author4=A. Spannenberg |author5=A. Arrieta |author6=A. Preetz |author7=D. Heller |title=Cationic Rh-bisphosphine-diolefin complexes as precatalysts for enantioselective catalysis––what information do single crystal structures contain regarding product chirality?|pages=2139–50|doi=10.1016/j.tetasy.2004.06.036|year=2004}}</ref>]]

{{clear}}
==References==
{{Reflist}}

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