Bis(2,4,6-trimethylphenyl)phosphorus Chloride

[67950-05-4] C18H22ClP (MW 304.79) InChI = 1S/C18H22ClP/c1-11-7-13(3)17(14(4)8-11)20(19)18-15(5)9-12(2)10-16(18)6/h7-10H,1-6H3 InChIKey = AZIJQQZQDFCANM-UHFFFAOYSA-N (reagent may be used for nucleophilic substitution at the phosphorus atom) Alternate names: dimesitylchlorophosphine; dimesitylphosphorus chloride. Physical Data: mp 80–85 °C; 1H NMR (301.24 MHz, C6D6) δ 6.60 (d, J = 3.2 Hz, 4H), 2.38 (d, J = 2.0 Hz, 12 H), 2.01 (s, 6 H). 13C NMR (62.90 MHz, C6D6) δ 142.28 (d, J = 18.3 Hz), 140.05, 133.61 (d, J = 46.3), 131.10 (d, J = 2.0 Hz), 23.31 (d, J = 15.8 Hz), 21.20. 31P NMR (101.26 MHz, C6D6) δ 85.0. MS (FAB+): 269 (M − Cl)+. Anal. calcd. for C18H22PCl: C, 70.93; H, 7.27. Found: C, 68.67; H, 7.99.1 Solubility: sol benzene, ether, THF, dichloromethane, hexane. Form Supplied in: pale yellow solid; commercially available. Preparative Methods: PCl(Mes)2 (Mes = mesityl = 2,4,6-trimethylphenyl) was first prepared by the addition of 2 equiv of (2,4,6-trimethylphenyl)magnesium bromide to phosphorus trichloride.2 It was later observed that this method gave a mixture of PCl(Mes)2 and PBr(Mes)2;3, 4 however, this mixture has been successfully used in substitution reactions.5 The addition of (2,4,6-trimethylphenyl)lithium to phosphorus trichloride6, 7 or to PCl2NEt2 (followed by the acidification with HCl)8 has also been reported to produce PCl(Mes)2 in good yields. Finally, it is also possible to synthesize PCl(Mes) from Mes2P(O)H by a reaction with phosphorus trichloride.1 Handling, Storage, and Precautions: sensitive to air and moisture and should be stored under inert atmosphere.