Triphenylarsine
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Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox headerbarTemplate:Chembox HazardsTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Yesno| Template:Longitem | Template:Unbulleted list |
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| UN number | 3465 |
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| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | Colourless solid |
| Density | 1.395 g cm−3 |
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| Solubility | Soluble in ethyl ether, benzene, slightly soluble in ethanol |
| Template:Longitem | −177.0·10−6 cm3/mol |
| Template:Longitem | Triclinic |
| Template:Longitem | Trimethylarsine |
| Template:Longitem | Triphenylamine |
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Triphenylarsine is the chemical compound with the formula As(C6H5)3. This organoarsenic compound, often abbreviated AsPh3, is a colorless crystalline solid that is used as a ligand and a reagent in coordination chemistry and organic synthesis. The molecule is pyramidal with As-C distances of 1.942–1.956 Å and C-As-C angles of 99.6–100.5°.[1]
This compound is prepared by the Wurtz reaction of arsenic trichloride with chlorobenzene using sodium as the reducing agent:[2]
- AsCl3 + 3 PhCl + 6 Na → AsPh3 + 6 NaCl
Reactions
Reaction of triphenylarsine with lithium gives lithium diphenylarsenide and phenyllithium:[3]
- AsPh3 + 2 Li → LiAsPh2 + LiPh
Triphenylarsine is the precursor to tetraphenylarsonium chloride, [AsPh4]Cl, a popular precipitating agent.[2]
AsPh3 forms metal complexes with metals. Most are analogues of the corresponding triphenylphosphine derivatives. Examples include [IrCl(CO)(AsPh3)]2, [RhCl(AsPh3)3], and [Fe(CO)4(AsPh3)].[4]
Tetraphenylarsonium chloride is prepared from triphenylarsine:[5]
- (C6H5)3As + Br2 → (C6H5)3AsBr2
- (C6H5)3AsBr2 + H2O → (C6H5)3AsO + 2 HBr
- (C6H5)3AsO + C6H5MgBr → (C6H5)4AsOMgBr
- (C6H5)4AsOMgBr + 3 HCl → (C6H5)4AsCl.HCl + MgBrCl
- (C6H5)4AsCl.HCl + NaOH → (C6H5)4AsCl + NaCl + H2O
References
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- ↑ Mazhar-ul-Haque, Hasan A. Tayim, Jamil Ahmed, and William Horne "Crystal and molecular structure of triphenylarsine" Journal of Chemical Crystallography Volume 15, Number 6 / 1985. Script error: No such module "CS1 identifiers".
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