Identifiers | |
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3D model (
JSmol)
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ChemSpider | |
ECHA InfoCard | 100.034.636 |
EC Number |
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PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
|
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Properties | |
C18H15AuClP | |
Molar mass | 494.71 g·mol−1 |
Appearance | Colorless solid |
Density | 1.97 g/cm3 |
Melting point | 236–237 °C (457–459 °F; 509–510 K) |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Chloro(triphenylphosphine)gold(I) or triphenylphosphinegold(I) chloride is a coordination complex with the formula ( Ph3P)AuCl. This colorless solid is a common reagent for research on gold compounds.
The complex is prepared by reducing chloroauric acid with triphenylphosphine in 95% ethanol: [1] [2]
Ph3PAuCl can also be prepared by treating a thioether complex of gold like (dimethyl sulfide)gold(I) chloride, [(Me2S)AuCl], with triphenylphosphine. [3]
The complex adopts a linear coordination geometry, which is typical of most gold(I) compounds. [4] It crystallizes in the orthorhombic space group P212121 with a = 12.300(4) Å, b = 13.084(4) Å, c = 10.170(3) Å with Z = 4 formula units per unit cell. [5]
Triphenylphosphinegold(I) chloride is a popular stable precursor for a cationic gold(I) catalyst used in organic synthesis. [3] Typically, it is treated with silver(I) salts of weakly coordinating anions (e.g., X– = SbF6–, BF4–, TfO–, or Tf2N–) to generate a weakly bound Ph3PAu–X complex, in equilibrium with the catalytically-active species [Ph3PAu]+X– in solution. Among these, only the bistriflimide complex Ph3PAuNTf2 can be isolated as the pure compound. [6] The nitrate complex Ph3PAuONO2 and the oxonium species [(Ph3PAu)3O]+[BF4– are also prepared from the chloride. [7]
As shown in the scheme below, the methyl complex Ph3PAuMe is prepared from triphenylphosphinegold(I) chloride by transmetalation with a Grignard reagent. Further treatment of Ph3PAuMe with methyllithium displaces the phosphine ligand and generates lithium di- and tetramethylaurate, Li+[AuMe2– and Li+[AuMe4–, respectively. [8] [9]
Identifiers | |
---|---|
3D model (
JSmol)
|
|
ChemSpider | |
ECHA InfoCard | 100.034.636 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
Properties | |
C18H15AuClP | |
Molar mass | 494.71 g·mol−1 |
Appearance | Colorless solid |
Density | 1.97 g/cm3 |
Melting point | 236–237 °C (457–459 °F; 509–510 K) |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Chloro(triphenylphosphine)gold(I) or triphenylphosphinegold(I) chloride is a coordination complex with the formula ( Ph3P)AuCl. This colorless solid is a common reagent for research on gold compounds.
The complex is prepared by reducing chloroauric acid with triphenylphosphine in 95% ethanol: [1] [2]
Ph3PAuCl can also be prepared by treating a thioether complex of gold like (dimethyl sulfide)gold(I) chloride, [(Me2S)AuCl], with triphenylphosphine. [3]
The complex adopts a linear coordination geometry, which is typical of most gold(I) compounds. [4] It crystallizes in the orthorhombic space group P212121 with a = 12.300(4) Å, b = 13.084(4) Å, c = 10.170(3) Å with Z = 4 formula units per unit cell. [5]
Triphenylphosphinegold(I) chloride is a popular stable precursor for a cationic gold(I) catalyst used in organic synthesis. [3] Typically, it is treated with silver(I) salts of weakly coordinating anions (e.g., X– = SbF6–, BF4–, TfO–, or Tf2N–) to generate a weakly bound Ph3PAu–X complex, in equilibrium with the catalytically-active species [Ph3PAu]+X– in solution. Among these, only the bistriflimide complex Ph3PAuNTf2 can be isolated as the pure compound. [6] The nitrate complex Ph3PAuONO2 and the oxonium species [(Ph3PAu)3O]+[BF4– are also prepared from the chloride. [7]
As shown in the scheme below, the methyl complex Ph3PAuMe is prepared from triphenylphosphinegold(I) chloride by transmetalation with a Grignard reagent. Further treatment of Ph3PAuMe with methyllithium displaces the phosphine ligand and generates lithium di- and tetramethylaurate, Li+[AuMe2– and Li+[AuMe4–, respectively. [8] [9]