:2-Diphenylphosphinobenzaldehyde
{{Orphan|date=June 2024}}
{{chembox
| Verifiedfields =
| verifiedrevid =
| ImageFile1 = 2-Diphenylphosphinobenzaldehyde.svg
| ImageSize1 =
| ImageFile2 =
| ImageSize2 =
| PIN = 2-(Diphenylphosphanyl)benzaldehyde
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 50777-76-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5M9BQ2FEC8
| PubChem = 2754316
| ChemSpiderID = 2035266
| SMILES = C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3C=O
| InChI = 1/C19H15OP/c20-15-16-9-7-8-14-19(16)21(17-10-3-1-4-11-17)18-12-5-2-6-13-18/h1-15H
| InChIKey = DRCPJRZHAJMWOU-UHFFFAOYAH
| StdInChI = 1S/C19H15OP/c20-15-16-9-7-8-14-19(16)21(17-10-3-1-4-11-17)18-12-5-2-6-13-18/h1-15H
| StdInChIKey = DRCPJRZHAJMWOU-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| Formula = C19H15OP
| MolarMass =
| Appearance = yellow solid
| Density =
| MeltingPtC = 118 to 119
| MeltingPt_notes =
| BoilingPt =
| Solubility =
}}
}}
2-Diphenylphosphinobenzaldehyde is a phosphine ligand with the formula (C6H5)2PC6H4CHO. It is a yellow solid that dissolves in common organic solvents.
Synthesis and reactions
2-Diphenylphosphinobenzaldehyde was first prepared by the reaction of chlorodiphenylphosphine with the Grignard reagent derived from the protected 2-bromobenzaldehyde, followed by deprotection.{{cite book|doi = 10.1002/9780470132524.ch39|chapter = 39. Substituted Triaryl Phosphines|title = Inorganic Syntheses|year = 2007|last1 = Hoots|first1 = John E.|last2 = Rauchfuss|first2 = Thomas B.|last3 = Wrobleski|first3 = Debra A.|last4 = Knachel|first4 = Howard C.|pages = 175–179|isbn = 9780470132524}}Schiemenz, Guenter P.; Kaack, Hermann "Aromatische Phosphine mit Substituenten zweiter Ordnung, XIII. Triarylphosphine mit mehreren Carbonyl-Funktionen durch Grignard-Synthese (Aromatic phosphines with second order substituents. XIII. Preparation of triarylphosphines with several carbonyl functions by Grignard synthesis)" Justus Liebigs Annalen der Chemie 1973, vol. 9, pp. 1480-93. {{doi|10.1002/jlac.197319730910}}. It can also be derived from (2-lithiophenyl)diphenylphosphine.
The compound condenses with a variety of amines to give phosphine-imine and phosphine-amine ligands.{{cite journal|doi=10.1021/ja003698p|title=Modular Peptide-Based Phosphine Ligands in Asymmetric Catalysis: Efficient and Enantioselective Cu-Catalyzed Conjugate Additions to Five-, Six-, and Seven-Membered Cyclic Enones|year=2001|last1=Degrado|first1=Sylvia J.|last2=Mizutani|first2=Hirotake|last3=Hoveyda|first3=Amir H.|journal=Journal of the American Chemical Society|volume=123|issue=4|pages=755–756|pmid=11456598|bibcode=2001JAChS.123..755D }}{{cite journal |doi=10.15227/orgsyn.097.0262|title=Stereoselective Synthesis of Chiral Sulfinamide Monophosphine Ligands (Ming-Phos)(S, Rs)-M|year=2020|last1=Hu|first1=Anjing|first2=Zhan-Ming|last2=Zhang|first3=Yuanjing|last3=Xiao|first4=Junliang|last4=Zhang|journal=Organic Syntheses|volume=97|pages=262–273|s2cid=235020219|doi-access=free}}
References
{{DEFAULTSORT:Diphenylphosphinobenzaldehyde, 2-}}