Molecules 2012, 17
10940
(3-Amino-1-hydroxypropylidene)bisphosphonic acid (1; CAS Registry Number 40391-99-9). The pH
1
was adjusted to 4.5 to obtain the monosodium salt, yield 22%; H-NMR (D2O/NaOD, 500.1 MHz) δ
2.97–2.90 (2H, t, J = 7.8 Hz), 2.10–1.99 (2H, m); 13C-NMR (D2O/NaOD, 125.8 MHz): 78.7
(t, 1JCP = 133.8 Hz), 40.9, 40.0 (t, 2JCP = 5.7 Hz); 31P-NMR (D2O/NaOD, 202.5 MHz): δ 18.46 (s); IR
(KBr) 3354, 3188, 2792, 2364, 1719, 1615, 1528, 1409, 1343, 1327, 1282, 1173, 1045, 984, 937, 895,
855, 775, 715, 683, 614 cm−1. Anal. Calcd. for C3H10NO7P2Na: C, 14.02; H, 3.92; N, 5.45; P, 24.1.
Found: C, 14.48; H, 4.41; N, 5.64; P, 23.3.
(5-Amino-1-hydroxypentylidene)bisphosphonic acid (3; CAS Registry Number 89732-96-7). Yield
1
86%; H-NMR (D2O/NaOD, 500.1 MHz): δ 2.70 (2H, t, J = 7.0 Hz), 1.94–1.82 (2H, m), 1.66–1.57
(2H, m), 1.51–1.43 (2H, m); 13C-NMR (D2O/NaOD, 125.8 MHz): 79.2 (t, 1JCP = 133.5 Hz), 42.9, 38.1,
2
31
34.3, 24.1 (t, JCP = 5.3 Hz); P-NMR (D2O/NaOD, 202.5 MHz): δ 18.92 (s); IR (KBr) 3209, 2959,
2331, 1617, 1503, 1468, 1452, 1219–939, 824, 663 cm−1. Anal. Calcd. for C5H15NO7P2: C, 22.82;
H, 5.75; N, 5.32; P, 23.5. Found: C, 22.59; H, 5.82; N, 5.30; P, 23.5.
(6-Amino-1-hydroxyhexylidene)bisphosphonic acid (4; CAS Registry Number 79778-41-9). Yield
1
88%; H-NMR (D2O/NaOD, 500.1 MHz): δ 2.61 (2H, t, J = 7.0 Hz), 1.94–1.82 (2H, m), 1.62–1.53
(2H, m), 1.51–1.43 (2H, m), 1.34–1.26 (2H, m); 13C-NMR (D2O/NaOD, 125.8 MHz): 79.6
(t, 1JCP = 134.4 Hz), 43.5, 39.0, 34.7, 30.4, 26.9 (t, 2JCP = 5.2 Hz); 31P-NMR (D2O/NaOD, 202.5 MHz):
δ 19.12 (s); IR (KBr) 3178, 2953, 2296, 1648, 1582, 1496, 1476, 1441, 1112, 1034, 997, 939, 905,
824, 777, 724, 657 cm−1. Anal. Calcd. for C6H17NO7P2: C, 26.00; H, 6.18; N, 5.05; P, 22.4. Found: C,
25.97; H, 6.17; N, 4.97; P, 22.2.
(8-Amino-1-hydroxyoctylidene)bisphosphonic acid (5; CAS Registry Number: 144050-49-7). Yield
1
75%; H-NMR (D2O/NaOD, 500.1 MHz): δ 2.62 (2H, t, J = 7.0 Hz), 1.93–1.81 (2H, m), 1.61–1.52
(2H, m), 1.50–1.41 (2H, m), 1.39–1.24 (6H, m); 13C-NMR (D2O/NaOD, 125.8 MHz): 78.9
1
2
(t, JCP = 132.4 Hz), 43.2, 38.4, 33.6, 33.0, 31.5, 29.0, 27.0 (t, JCP = 5.6 Hz); 31P-NMR (D2O/NaOD,
202.5 MHz): δ 19.05 (s); IR (KBr) 3327, 3150, 2901, 2848, 2276, 1650, 1620, 1541, 1471, 1398,
1334, 1300, 1224, 1151, 1079, 967, 842, 813, 767, 729, 647 cm−1. Anal. Calcd. for C8H21NO7P2: C,
31.48; H, 6.93; N, 4.59; P, 20.3. Found: C, 31.44; H, 6.98; N, 4.69; P, 20.5.
(9-Amino-1-hydroxynonylidene)bisphosphonic acid (6; CAS Registry Number: 144050-48-6). As an
exception to the general method 6 was refluxed for 5 h in 2 M HCl instead of water and pH was
adjusted to 7 to obtain the disodium salt. The product was recrystallized from water-ethanol, yield
1
63%; H-NMR (D2O/NaOD, 500.1 MHz): δ 2.59 (2H, t, J = 7.0 Hz), 1.93–1.79 (2H, m), 1.59–1.50
(2H, m), 1.50–1.38 (2H, m), 1.37–1.21 (8H, m); 13C-NMR (D2O/NaOD, 125.8 MHz): 79.6
1
2
(t, JCP = 134.6 Hz), 43.4, 39.0, 34.7, 33.2, 31.9, 31.7, 28.9, 27.2 (t, JCP = 5.2 Hz); 31P-NMR
(D2O/NaOD, 202.5 MHz): δ 19.30 (s); IR (KBr) 3195, 2910, 2850, 1637, 1558, 1475, 1168, 1040,
906, 720, 672 cm−1. Anal. Calcd. for C9H23NO7P2 H2O: C, 32.05; H, 7.47; N, 4.15; P, 18.4. Found: C,
31.55; H, 6.88; N, 3.92; P, 18.6.
(10-Amino-1-hydroxydecylidene)bisphosphonic acid (7). As an exception to the general method 7 was
refluxed for 5 h in 2 M HCl instead of water and the product was washed with water, yield 66%;