Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Triphenylstibine: Difference between pages

|Watchedfields = changed

|verifiedrevid = 470616981

|Name = Triphenylstibine

|ImageFile1 = Triphenylstibine-3D-balls.png

|ImageAlt1 = Ball-and-stick model of the triphenylstibine molecule

|ImageFile2 = Triphenylstibine_crystals.jpg

|PIN = Triphenylstibane

|OtherNames = Triphenylantimony

|Section1={{Chembox Identifiers

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

|CASNo = 603-36-1

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

|ChemSpiderID = 11284

|EC_number = 210-037-6

|PubChem = 11777

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

|UNII = G1X1263AMM

|RTECS = WJ1400000

|InChI = 1/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H;/rC18H15Sb/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

|InChIKey = HVYVMSPIJIWUNA-KWOBPOEBAA

|SMILES = c3c([Sb](c1ccccc1)c2ccccc2)cccc3

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

|StdInChI = 1S/3C6H5.Sb/c3*1-2-4-6-5-3-1;/h3*1-5H;

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

|StdInChIKey = HVYVMSPIJIWUNA-UHFFFAOYSA-N

|Section2={{Chembox Properties

|Formula = C₁₈H₁₅Sb

|MolarMass = 353.07 g/mol

|Appearance = Colourless solid

|Density = 1.53 g/cm³

|Solubility = insoluble

|MeltingPtC = 52 to 54

|BoilingPtC = 377

}}

|Section3={{Chembox Structure

|MolShape = [[trigonal pyramidal]]

}}

|Section7={{Chembox Hazards

|MainHazards = mildly toxic

|NFPA-H = 1

|GHS_ref=<ref>{{cite web |title=Triphenylantimony |url=https://pubchem.ncbi.nlm.nih.gov/compound/11777#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=12 December 2021 |language=en}}</ref>

|GHSPictograms = {{GHS06}}{{GHS07}}{{GHS09}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|301|302|332|411}}

|PPhrases = {{P-phrases|261|264|270|271|273|301+310|301+312|304+312|304+340|312|330|391|405}}

}}

|Section4={{Chembox Related

|OtherCompounds = [[Triphenylamine]]<br>[[Triphenylphosphine]]<br />[[Triphenylarsine]]<br />[[Stibine]]}}

}}

'''Triphenylstibine''' is the [[chemical compound]] with the [[chemical formula|formula]] Sb(C₆H₅)₃. Abbreviated SbPh₃, this colourless solid is often considered the prototypical organoantimony compound. It is used as a [[ligand]] in [[coordination chemistry]]<ref name=McAuliffe>{{cite book|editor=C. A. McAuliffe|title=Transition Metal Complexes of Phosphorus, Arsenic, and Antimony Ligands|publisher=J. Wiley|year=1973|isbn=0-470-58117-4}}</ref> and as a reagent in [[organic synthesis]].

Like the related molecules [[triphenylamine]], [[triphenylphosphine]] and [[triphenylarsine]], SbPh₃ is pyramidal with a propeller-like arrangement of the phenyl groups. The Sb-C distances average 2.14-2.17 Å and the C-Sb-C angle are 95°.<ref>Adams, E. A.; Kolis, J. W.; Pennington, W. T. "Structure of triphenylstibine" Acta Crystallographica 1990, volume C46, pp. 917-919. {{doi|10.1107/S0108270189012862}}</ref>

SbPh₃ was first reported in 1886, being prepared from [[antimony trichloride]] by the reaction:<ref>[[August Michaelis|Michaelis, A.]]; Reese, A. "Ueber<!--yes, Ueber, no umlaut--> die Verbindungen der Elemente der Stickstoffgruppe mit den Radicalen der aromatischen Reihe. Achte Abhandlung Ueber aromatische Antimonverbindungen" Liebigs Annallen der Chemie volume 233, pages 39-60 (1886). {{doi|10.1002/jlac.18862330104}}.</ref>

:6 Na + 3 C₆H₅Cl + SbCl₃ → (C₆H₅)₃Sb + 6 NaCl

An alternative method treats [[phenylmagnesium bromide]] with SbCl₃.<ref>{{cite journal|author=Hiers, G. S.|title=Triphenylstibine|journal=Organic Syntheses|year=1927|volume=7|page=80|doi=10.15227/orgsyn.007.0080}}</ref>

==References==

{{reflist}}{{Antimony compounds}}

[[Category:Organoantimony compounds]]

[[Category:Phenyl compounds]]