2-Diphenylphosphinobenzaldehyde

2-Diphenylphosphinobenzaldehyde
Names
	Preferred IUPAC name 2-(Diphenylphosphanyl)benzaldehyde
Identifiers
CAS Number	50777-76-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	2035266;
ECHA InfoCard	100.156.047
PubChem CID	2754316;
UNII	5M9BQ2FEC8 ;
CompTox Dashboard (EPA)	DTXSID50373019 ;
	InChI InChI=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 Key: DRCPJRZHAJMWOU-UHFFFAOYSA-N; 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 Key: DRCPJRZHAJMWOU-UHFFFAOYAH;
	SMILES C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3C=O;
Properties
Chemical formula	C19H15OP
Appearance	yellow solid
Melting point	118 to 119 °C (244 to 246 °F; 391 to 392 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[1]^[2] 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.^[3]^[4]

References

^ Hoots, John E.; Rauchfuss, Thomas B.; Wrobleski, Debra A.; Knachel, Howard C. (2007). "39. Substituted Triaryl Phosphines". Inorganic Syntheses. pp. 175–179. doi:10.1002/9780470132524.ch39. 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.
^ Degrado, Sylvia J.; Mizutani, Hirotake; Hoveyda, Amir H. (2001). "Modular Peptide-Based Phosphine Ligands in Asymmetric Catalysis: Efficient and Enantioselective Cu-Catalyzed Conjugate Additions to Five-, Six-, and Seven-Membered Cyclic Enones". Journal of the American Chemical Society. 123 (4): 755–756. doi:10.1021/ja003698p. PMID 11456598.
^ Hu, Anjing; Zhang, Zhan-Ming; Xiao, Yuanjing; Zhang, Junliang (2020). "Stereoselective Synthesis of Chiral Sulfinamide Monophosphine Ligands (Ming-Phos)(S, Rs)-M". Organic Syntheses. 97: 262–273. doi:10.15227/orgsyn.097.0262. S2CID 235020219.

[1] Hoots, John E.; Rauchfuss, Thomas B.; Wrobleski, Debra A.; Knachel, Howard C. (2007). "39. Substituted Triaryl Phosphines". Inorganic Syntheses. pp. 175–179. doi:10.1002/9780470132524.ch39. ISBN 9780470132524.

[2] 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.

[3] Degrado, Sylvia J.; Mizutani, Hirotake; Hoveyda, Amir H. (2001). "Modular Peptide-Based Phosphine Ligands in Asymmetric Catalysis: Efficient and Enantioselective Cu-Catalyzed Conjugate Additions to Five-, Six-, and Seven-Membered Cyclic Enones". Journal of the American Chemical Society. 123 (4): 755–756. doi:10.1021/ja003698p. PMID 11456598.

[4] Hu, Anjing; Zhang, Zhan-Ming; Xiao, Yuanjing; Zhang, Junliang (2020). "Stereoselective Synthesis of Chiral Sulfinamide Monophosphine Ligands (Ming-Phos)(S, Rs)-M". Organic Syntheses. 97: 262–273. doi:10.15227/orgsyn.097.0262. S2CID 235020219.

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