4,5‐Bis(1,1‐dimethylethyl)‐6‐ethoxy‐2,2‐dimethyl‐3,7‐dioxa‐4‐aza‐6‐phosphanonanoic Acid 6‐Oxide

[654636-62-1] C17H36NO6P (MW 381.44) InChI = 1S/C17H36NO6P/c1-11-22-25(21,23-12-2)13(15(3,4)5)18(16(6,7)8)24-17(9,10)14(19)20/h13H,11-12H2,1-10H3,(H,19,20) InChIKey = LHCFAZQDKKRUDE-UHFFFAOYSA-N (initiating/controlling agent for nitroxide-mediated polymerization (NMP),1 complex architecture synthesis2 and radical cyclization3) Alternate names: BlocbuilderTM. Physical data: mp 114–118 °C (decomp.), SADT 52 °C. Solubility: soluble in aromatic solvents, EtOH (400  g L−1 at 20 °C), CH2Cl2 (290 g L−1 at 20 °C), acetone (55  g L−1) and poorly soluble in water (54.2 mg L−1). Form supplied in: white solid. Analysis of Reagent Purity: 31P NMR: δ = 26.2. 1H NMR: δ = 4.4–3.9 (m, 4 H; CH2), 3.42 (d, 2JH,P = 27  Hz, 1 H; CHP), 1.78 (s, 3 H; CH3), 1.61 (s, 3 H; CH3), 1.36 (t, 3JH,H = 6 Hz, 3 H), 1.33 (t, 3JH,H = 6 Hz, 3 H), 1.24 (s, 9 H; tBu), 1.15 (s, 9 H; tBu). 13C NMR: δ = 176.5 (C=0), 84.5 (OCCO), 70.8 (d, 1JC,P = 136  Hz, CHP), 63.0 (CN), 62.06 (d, 2JC,P = 6.6  Hz, CH2), 59.94 (d, 2JC,P = 7.5 Hz, CH2), 35.74 (d, 2JC,P = 6.0  Hz, PCC), 29.5 (d, 3JC,P = 6.0 Hz, PCC(CH3)3), 27.9 (NC(CH3)3), 27.4 (CH3), 24.1 (CH3), 16.15 (d, 3JC,P = 6.0  Hz, OCH2CH3), 15.77 (d, 2JC,P = 7.5  Hz, OCH2CH3). Anal. calcd. for C17H36NO6P: C, 53.53; H, 9.51; N, 3.67; found: C, 53.57; H, 9.28; N, 3.77. Handling, Storage, and Precautions: store below +30 °C, DL50/oral/rat >2000  mg kg−1.