triphenylarsine

{{Chembox

| Watchedfields = changed

| verifiedrevid = 470616659

| ImageFile1 = TriphenylarsinePic.svg

| ImageFile2 = Triphenylarsine-3D-balls.png

| ImageSize2 = 244

| ImageName2 = Ball and stick model of aromatic triphenylarsine

| PIN = Triphenylarsane

| SystematicName =

| OtherNames = Tribenzenidoarsenic

Triphenylarsine

|Section1={{Chembox Identifiers

| CASNo = 603-32-7

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = MN8EZ3FL74

| PubChem = 11773

| ChemSpiderID = 11280

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 210-032-9

| UNNumber = 3465

| RTECS = CH8942500

| SMILES = C1=CC=C(C=C1)[As](C1=CC=CC=C1)C1=CC=CC=C1

| SMILES1 = c1ccc(cc1)[As](c2ccccc2)c3ccccc3

| StdInChI = 1S/C18H15As/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| InChI = 1/C18H15As/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

| StdInChIKey = BPLUKJNHPBNVQL-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| InChIKey = BPLUKJNHPBNVQL-UHFFFAOYAO}}

|Section2={{Chembox Properties

| C=18 | H=15 | As=1

| Appearance = Colourless solid

| Density = 1.395 g cm⁻³

| MeltingPtC = 58 to 61

| BoilingPtC = 373

| BoilingPt_notes = at 760 mmHg

| Solubility = Insoluble

| SolubleOther = Soluble in ethyl ether, benzene, slightly soluble in ethanol

| MagSus = −177.0·10⁻⁶ cm³/mol

}}

|Section3={{Chembox Structure

| CrystalStruct = Triclinic}}

|Section4={{Chembox Hazards

| GHSPictograms = {{GHS06}}{{GHS09}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|301|331|410}}

| PPhrases = {{P-phrases|261|264|270|271|273|301+310|304+340|311|321|330|391|403+233|405|501}}

}}

|Section5={{Chembox Related

| OtherFunction_label = organoarsanes

| OtherFunction = Trimethylarsine

| OtherCompounds = Triphenylamine

Triphenylborane

Triphenylphosphine

Triphenylstibine

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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°.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. {{doi| 10.1007/BF01164771}}

This compound is prepared by the Wurtz reaction of arsenic trichloride with chlorobenzene using sodium as the reducing agent:{{OrgSynth | author = Shriner, R. L.; Wolf, C. N. | title = Tetraphenylarsonium Chloride Hydrochloride | collvol = 4 | collvolpages = 910 | year = 1963 | prep = cv4p0910}} [http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0910 article]

:AsCl₃ + 3 PhCl + 6 Na → AsPh₃ + 6 NaCl