Names | |
---|---|
Preferred IUPAC name
(Ethane-1,2-diyl)bis(diphenylphosphane) | |
Other names
1,2-Bis(diphenylphosphino)ethane
Diphos Dppe | |
Identifiers | |
3D model (
JSmol)
|
|
761261 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.015.246 |
EC Number |
|
9052 | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C26H24P2 | |
Molar mass | 398.42 g/mol |
Melting point | 140 to 142 °C (284 to 288 °F; 413 to 415 K) |
Hazards | |
GHS labelling: | |
Warning | |
H302, H315, H319, H332, H335, H410 | |
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
1,2-Bis(diphenylphosphino)ethane (dppe) is an organophosphorus compound with the formula (Ph2PCH2)2 (Ph = phenyl). It is a common symmetrical bidentate ligand in coordination chemistry. It is a white solid that is soluble in organic solvents.
The preparation of dppe entails the alkylation of NaP(C6H5)2 with 1,2-dichloroethane: [1] [2]
The reduction of dppe by lithium give the disecondary phosphine: [3]
Hydrolysis gives the bis(secondary phosphine).
Treatment of dppe with hydrogen peroxide pproduces the phosphine oxides (C6H5)2P(O)CH2CH2P(C6H5)2 and (C6H5)2P(O)CH2CH2P(O)(C6H5)2. [4] Selective mono-oxidation of dppe can be achieved by benzylation followed by hydrolysis:
Hydrogenation of dppe gives the ligand bis(dicyclohexylphosphino)ethane.
Many coordination complexes of dppe are known, and some are used as homogeneous catalysts. Dppe is almost invariably chelating, although there are examples of monodentate (e.g., W(CO)5(dppe)) and of bridging behavior. [5] The natural bite angle is 86°. [6]
Names | |
---|---|
Preferred IUPAC name
(Ethane-1,2-diyl)bis(diphenylphosphane) | |
Other names
1,2-Bis(diphenylphosphino)ethane
Diphos Dppe | |
Identifiers | |
3D model (
JSmol)
|
|
761261 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.015.246 |
EC Number |
|
9052 | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C26H24P2 | |
Molar mass | 398.42 g/mol |
Melting point | 140 to 142 °C (284 to 288 °F; 413 to 415 K) |
Hazards | |
GHS labelling: | |
Warning | |
H302, H315, H319, H332, H335, H410 | |
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
1,2-Bis(diphenylphosphino)ethane (dppe) is an organophosphorus compound with the formula (Ph2PCH2)2 (Ph = phenyl). It is a common symmetrical bidentate ligand in coordination chemistry. It is a white solid that is soluble in organic solvents.
The preparation of dppe entails the alkylation of NaP(C6H5)2 with 1,2-dichloroethane: [1] [2]
The reduction of dppe by lithium give the disecondary phosphine: [3]
Hydrolysis gives the bis(secondary phosphine).
Treatment of dppe with hydrogen peroxide pproduces the phosphine oxides (C6H5)2P(O)CH2CH2P(C6H5)2 and (C6H5)2P(O)CH2CH2P(O)(C6H5)2. [4] Selective mono-oxidation of dppe can be achieved by benzylation followed by hydrolysis:
Hydrogenation of dppe gives the ligand bis(dicyclohexylphosphino)ethane.
Many coordination complexes of dppe are known, and some are used as homogeneous catalysts. Dppe is almost invariably chelating, although there are examples of monodentate (e.g., W(CO)5(dppe)) and of bridging behavior. [5] The natural bite angle is 86°. [6]