1,2-Bis(dimethylphosphino)ethane: Difference between revisions

1,2-Bis(dimethylphosphino)ethane
Names
	Preferred IUPAC name (Ethane-1,2-diyl)bis(dimethylphosphane)
	Other names DMPE; ethylenebis(dimethylphosphine); 1,2-Bis(dimethylphosphino)ethane
Identifiers
CAS Number	23936-60-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	124423 ;
ECHA InfoCard	100.155.809
EC Number	627-450-6;
PubChem CID	141059;
UNII	9P3522CZ8T ;
CompTox Dashboard (EPA)	DTXSID70178649 ;
	InChI InChI=1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 Key: ZKWQSBFSGZJNFP-UHFFFAOYSA-N ; InChI=1/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3 Key: ZKWQSBFSGZJNFP-UHFFFAOYAN;
	SMILES P(C)(C)CCP(C)C;
Properties
Chemical formula	C6H16P2
Molar mass	150.142 g·mol−1
Density	0.9 g/mL at 25 °C
Boiling point	180 °C (356 °F; 453 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H250, H315, H319, H335
Precautionary statements	P210, P222, P231, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P335+P334, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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1,2-Bis(dimethylphosphino)ethane (dmpe) is a diphosphine ligand in coordination chemistry. It is a colorless, air-sensitive liquid that is soluble in organic solvents. With the formula (CH₂PMe₂)₂, dmpe is used as a compact strongly basic spectator ligand (Me = methyl), Representative complexes include V(dmpe)₂(BH₄)₂, Mn(dmpe)₂(AlH₄)₂, Tc(dmpe)₂(CO)₂Cl, and Ni(dmpe)Cl₂.^[2]

Structure of *trans*-CoCl₂(dmpe)₂ (P is ochre, Co. is blue, Cl is green).

Synthesis

It is synthesised by the reaction of methylmagnesium iodide with 1,2-bis(dichlorophosphino)ethane:^[3]

Cl₂PCH₂CH₂PCl₂ + 4 MeMgI → Me₂PCH₂CH₂PMe₂ + 4 MgICl

Alternatively it can be generated by alkylation of sodium dimethylphosphide.

The synthesis of dmpe from thiophosphoryl chloride has led to serious accidents and has been abandoned.^[4]

Related ligands

Bis(dicyclohexylphosphino)ethane, a bulkier analogue, which is also a solid.
1,2-Bis(diphenylphosphino)ethane, more air-stable than dmpe, but less basic.
1,2-Bis(dimethylphosphino)benzene, a more rigid analogue of dmpe.
Tetramethylethylenediamine, the diamine analogue of dmpe.

References

^ Sigma-Aldrich Co., 1,2-Bis(dimethylphosphino)ethane. Retrieved on 2013-07-20.
^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
^ R. J. Burt; J. Chatt; W. Hussain; G. J. Leigh (1979). "A convenient synthesis of 1,2-bis(dichlorophosphino)ethane, 1,2-bis(dimethylphosphino)ethane and 1,2-bis(diethylphosphino)ethane". Journal of Organometallic Chemistry. 182 (2): 203–6. doi:10.1016/S0022-328X(00)94383-3.
^ Bercaw, J. E.; Parshall, G. W. (1985). "Preparation of Tetramethyldiphosphine Disulfide and Ethylenebis(Dimethylphosphine) (Dmpe)". Inorganic Syntheses. Vol. 23. pp. 199–200. doi:10.1002/9780470132548.ch42. ISBN 9780470132548.

[sigma-1] Sigma-Aldrich Co., 1,2-Bis(dimethylphosphino)ethane. Retrieved on 2013-07-20.

[2] Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.

[3] R. J. Burt; J. Chatt; W. Hussain; G. J. Leigh (1979). "A convenient synthesis of 1,2-bis(dichlorophosphino)ethane, 1,2-bis(dimethylphosphino)ethane and 1,2-bis(diethylphosphino)ethane". Journal of Organometallic Chemistry. 182 (2): 203–6. doi:10.1016/S0022-328X(00)94383-3.

[4] Bercaw, J. E.; Parshall, G. W. (1985). "Preparation of Tetramethyldiphosphine Disulfide and Ethylenebis(Dimethylphosphine) (Dmpe)". Inorganic Syntheses. Vol. 23. pp. 199–200. doi:10.1002/9780470132548.ch42. ISBN 9780470132548.

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[2]

[3]

[4]

@@ Line 1: / Line 1: @@
 {{chembox
-| Verifiedfields = changed
+|Verifiedfields = changed
-| Watchedfields = changed
+|Watchedfields = changed
-| verifiedrevid = 477203110
+|verifiedrevid = 477203110
-| Name = 1,2-Bis(dimethylphosphino)ethane
+|Name = 1,2-Bis(dimethylphosphino)ethane
-| ImageFile = dmpe-2D-skeletal-B.png
+|ImageFile = dmpe-2D-skeletal-B.png
+|ImageFile1 = Dmpe-from-xtal-1997-3D-balls.png
-| ImageName =
+|PIN = (Ethane-1,2-diyl)bis(dimethylphosphane)
-| ImageFile1 = Dmpe-from-xtal-1997-3D-balls.png
+|OtherNames = DMPE<br>ethylenebis(dimethylphosphine)<br>1,2-Bis(dimethylphosphino)ethane
-| ImageName1 =
-| PIN = (Ethane-1,2-diyl)bis(dimethylphosphane)
-| OtherNames = DMPE<br>ethylenebis(dimethylphosphine)<br>1,2-Bis(dimethylphosphino)ethane
 |Section1={{Chembox Identifiers
-| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
-| ChemSpiderID = 124423
+|ChemSpiderID = 124423
-| InChI = 1/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3
+| EC_number = 627-450-6
+|InChI = 1/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3
-| SMILES = P(C)(C)CCP(C)C
+|SMILES = P(C)(C)CCP(C)C
-| InChIKey = ZKWQSBFSGZJNFP-UHFFFAOYAN
+|InChIKey = ZKWQSBFSGZJNFP-UHFFFAOYAN
-| PubChem = 141059
+|PubChem = 141059
-| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
-| StdInChI = 1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3
+|StdInChI = 1S/C6H16P2/c1-7(2)5-6-8(3)4/h5-6H2,1-4H3
-| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
-| StdInChIKey = ZKWQSBFSGZJNFP-UHFFFAOYSA-N
+|StdInChIKey = ZKWQSBFSGZJNFP-UHFFFAOYSA-N
+|CASNo = 23936-60-9
-| CASNo_Ref = {{cascite|changed|??}}
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-| CASNo = 23936-60-9
+|UNII_Ref = {{fdacite|correct|FDA}}
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 |Section2={{Chembox Properties
 |C=6|H=16|P=2
-| BoilingPtC = 180
+|BoilingPtC = 180
-| BoilingPt_notes =
+|BoilingPt_notes =
-| Density = 0.9 g/mL at 25&nbsp;°C
+|Density = 0.9 g/mL at 25&nbsp;°C
-  }}
+}}
-|Section4={{Chembox Hazards
+|Section7={{Chembox Hazards
-| GHSPictograms = {{GHS02}}{{GHS07}}<ref name="sigma">{{Sigma-Aldrich|Aldrich| id=261939 |name=1,2-Bis(dimethylphosphino)ethane|accessdate=2013-07-20}}</ref>
+|GHSPictograms = {{GHS02}}{{GHS07}}
-| NFPA-H =
+| GHSSignalWord = Danger
+| HPhrases = {{H-phrases|225|250|315|319|335}}
-| NFPA-F =
+| 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}}
-| NFPA-R =
+| GHS_ref=<ref name="sigma">{{Sigma-Aldrich|Aldrich| id=261939 |name=1,2-Bis(dimethylphosphino)ethane|accessdate=2013-07-20}}</ref>
-| FlashPt =
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-| AutoignitionPt =
-| LD50 =
- }}
 }}
 '''1,2-Bis(dimethylphosphino)ethane''' ('''dmpe''') is a [[diphosphine ligand]] in [[coordination chemistry]]. 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 [[spectator ligand]] (Me = [[methyl]]),  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>
-[[File:Trans-CoCl2(dmpe)2.png|thumb|left|Structure of ''trans''-CoCl{{sub|2}}(dmpe){{sub|2}} (P is ochre, Co. is blue, Cl is green.<!--CSDZIGFIEtr-->]]
+[[File:Trans-CoCl2(dmpe)2.png|thumb|left|Structure of ''trans''-CoCl{{sub|2}}(dmpe){{sub|2}} (P is ochre, Co. is blue, Cl is green).<!--CSDZIGFIEtr-->]]
 ==Synthesis==
-It is synthesised by the reaction of [[methylmagnesium iodide]] with [[1,2-Bis(dichlorophosphino)ethane|1,2-bis(dichlorophosphino)ethane]]:<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=[[Journal of Organometallic Chemistry|J. Organomet. Chem.]] |volume=182 |issue=2 |year=1979 |pages=203–6 |doi=10.1016/S0022-328X(00)94383-3}}</ref>
+It is synthesised by the reaction of [[methylmagnesium iodide]] with [[1,2-Bis(dichlorophosphino)ethane|1,2-bis(dichlorophosphino)ethane]]:<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=[[Journal of Organometallic Chemistry]] |volume=182 |issue=2 |year=1979 |pages=203–6 |doi=10.1016/S0022-328X(00)94383-3}}</ref>
-: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
+: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
 Alternatively it can be generated by alkylation of sodium dimethylphosphide.
-The synthesis of dmpe from [[thiophosphoryl chloride]] 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)|series=Inorganic Syntheses|pages=199–200|year=1985|volume=23|last1=Bercaw|first1=J. E.|title=Inorganic Syntheses|last2=Parshall|first2=G. W.|isbn=9780470132548}}}</ref>
+The synthesis of dmpe from [[thiophosphoryl chloride]] 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>
 ==Related ligands==