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4,40-(Phenylmethylene)dianiline (3b).6a,6g,9a,9c,9d,9e CAS number
IR (neat): 3431, 3343, 2923, 1734, 1619, 1514, 1454, 1380, 1273,
1104, 1046, 820, 752, 549, 640 cmꢂ1; HRMS (ESI-TOF) m/z calcd
for C19H17Cl2N2 [M + H]+ 343.0763, found 343.0763.
603-40-7; 78% yield (0.2133 g) as a yellow solid; mp: 130–132 ꢀC;
1
Rf ¼ 0.33 (40% EtOAc/n-hexane); H-NMR (400 MHz, DMSO-d6):
4,40-((4-Methoxyphenyl)methylene)dianiline (3e).9a,9c CAS
number 848126-11-4; 81% yield (0.2468 g) as a brown solid; mp:
130–132 ꢀC; Rf ¼ 0.25 (40% EtOAc/n-hexane); 1H-NMR (400
MHz, DMSO-d6): d 6.95 (d, J ¼ 8.8 Hz, 2H), 6.81 (d, J ¼ 8.8 Hz,
2H), 6.70 (d, J ¼ 8.4 Hz, 4H), 6.46 (d, J ¼ 8.4 Hz, 4H), 5.11 (s, 1H),
4.85 (s, 4H), 3.69 (s, 3H); 13C-NMR (100 MHz, DMSO-d6): d 157.2,
146.5, 137.8, 132.3, 129.8, 129.3, 113.8, 113.4, 55.0, 53.8; IR
(neat): 3408, 3333, 3002, 2970, 1739, 1606, 1505, 1232, 1026,
d 7.24 (t, J ¼ 7.2 Hz, 2H), 7.14 (t, J ¼ 7.2 Hz, 1H) 7.06 (d, J ¼ 7.2 Hz,
2H), 6.73 (d, J ¼ 8.4 Hz, 4H), 6.47 (d, J ¼ 8.4 Hz, 4H), 5.17 (s, 1H),
4.88 (brs, 4H); 13C-NMR (100 MHz, DMSO-d6): d 146.6, 145.8,
131.9, 129.4, 128.9, 128.0, 125.6, 113.7, 54.6; IR (neat): 3420, 3338,
3211, 3021, 1739, 1618, 1509, 1268, 1177, 813, 698, 574, 556 cmꢂ1
.
2-((4-Aminophenyl)(phenyl)methyl)aniline (4b).9e CAS number
13168-31-5; 14% yield (0.0379 g) as a brown oil; Rf ¼ 0.45 (40%
EtOAc/n-hexane); 1H-NMR (400 MHz, DMSO-d6): d 7.27 (t, J ¼
7.2 Hz, 2H), 7.17 (t, J ¼ 7.6 Hz, 1H), 7.05 (d, J ¼ 7.2 Hz, 2H), 6.90
(td, J ¼ 8.0, 1.6 Hz, 1H), 6.71 (d, J ¼ 8.0 Hz, 2H), 6.62 (dd, J ¼ 8.0,
1.2 Hz, 1H), 6.54–6.44 (m, 4H), 5.30 (s, 1H), 4.92 (brs, 2H), 4.57
(brs, 2H); 13C-NMR (100 MHz, DMSO-d6): d 146.9, 145.6, 144.0,
129.7, 129.6, 129.1, 129.0, 128.2, 128.1, 126.6, 125.9, 116.0, 115.1,
113.9, 49.8; IR (neat): 3365, 300, 3209, 3001, 1739, 1618, 1509,
830, 559, 507 cmꢂ1
.
2-((4-Aminophenyl)(4-methoxyphenyl)methyl)aniline (4e).
13% yield (0.0403 g) as a yellow solid; mp: 120–122 ꢀC; Rf ¼ 0.31
(40% EtOAc/n-hexane); 1H-NMR (400 MHz, DMSO-d6): d 6.95 (d,
J ¼ 8.4 Hz, 2H), 6.90 (td, J ¼ 8.0, 1.6 Hz, 1H), 6.83 (d, J ¼ 8.8 Hz,
2H), 6.70 (d, J ¼ 8.4 Hz, 2H). 6.61 (dd, J ¼ 8.0, 0.8 Hz, 1H), 6.53
(dd, J ¼ 7.6, 1.6 Hz, 1H), 6.48 (d, J ¼ 8.4 Hz, 2H), 6.46 (td, J ¼ 8.0,
0.8 Hz, 1H), 5.23 (s, 1H), 4.90 (s, 2H), 4.53 (s, 2H), 3.71 (s, 3H);
13C-NMR (100 MHz, DMSO-d6): d 157.5, 146.8, 145.5, 135.8,
130.2, 130.0, 129.5, 129.0, 128.6, 126.6, 116.1, 115.1, 113.9,
113.5, 56.0, 49.1; IR (neat): 3365, 3001, 2926, 2853, 1894, 1618,
1507, 1242, 1175, 1029, 834, 751, 624, 580, 570, 548, 530, 509,
471, 446 cmꢂ1; HRMS (ESI-TOF) m/z calcd for C20H21N2O [M +
H]+ 305.1648, found 305.1645.
1268, 1177, 813, 698, 574, 556 cmꢂ1
.
4,40-((3-Nitrophenyl)methylene)dianiline (3c).9d CAS number
82646-09-1; 88% yield (0.2800 g) as a viscous brown oil; Rf ¼ 0.26
(40% EtOAc/n-hexane); 1H-NMR (400 MHz, DMSO-d6): d 8.04 (dt,
J ¼ 7.2, 2.4 Hz, 1H), 7.86 (brs, 1H), 7.55–7.51 (m, 2H), 6.75 (d, J ¼
8.0 Hz, 4H), 6.51 (d, J ¼ 8.4 Hz, 4H), 5.39 (s, 1H), 4.97 (brs, 4H);
13C-NMR (100 MHz, DMSO-d6): d 148.3, 147.7, 147.0, 135.7,
130.6, 129.5, 129.4, 123.0, 120.9, 113.9, 53.9; IR (neat): 3415,
3335, 3205, 3011, 1620, 1511, 1313, 1244, 1080, 745, 521 cmꢂ1
.
4-(Bis(4-aminophenyl)methyl)phenol (3f).6b,6h,6i,6j,6k,6l,9a CAS
number 110146-05-9; 88% yield (0.2552 g) as a brown solid; mp:
198–200 ꢀC; Rf ¼ 0.36 (50% EtOAc/n-hexane); 1H-NMR (400
MHz, DMSO-d6): d 9.14 (s, 1H), 6.83 (d, J ¼ 8.4 Hz, 2H), 6.69 (d, J
¼ 8.4 Hz, 4H), 6.63 (d, J ¼ 8.4 Hz, 2H), 6.45 (d, J ¼ 8.4 Hz, 4H),
5.04 (s, 1H), 4.85 (brs, 4H); 13C-NMR (100 MHz, DMSO-d6):
d 155.2, 146.4, 136.0, 132.6, 129.7, 129.3, 114.7, 113.7, 53.8; IR
(neat): 3233, 3021, 2876, 2704, 1612, 1600, 1442, 1359, 1171,
2-((4-Aminophenyl)(3-nitrophenyl)methyl)aniline (4c). 9%
yield (0.0299 g) as a yellow solid; mp: 70–72 ꢀC; Rf ¼ 0.37 (40%
EtOAc/n-hexane); 1H-NMR (400 MHz, DMSO-d6): d 8.07 (ddd, J ¼
8.0, 2.4, 1.2 Hz, 1H), 7.85 (t, J ¼ 2.0 Hz, 1H), 7.58 (t, J ¼ 7.6 Hz,
1H), 7.50 (d, J ¼ 7.6 Hz, 1H), 6.94 (td, J ¼ 7.6, 1.6 Hz, 1H), 6.72 (d,
J ¼ 8.4 Hz, 2H), 6.65 (dd, J ¼ 8.0, 0.8 Hz, 1H), 6.56–6.51 (m, 4H),
5.56 (s, 1H), 5.00 (brs, 2H), 4.76 (brs, 2H); 13C-NMR (100 MHz,
DMSO-d6): d 147.7, 147.2, 146.6, 145.8, 135.9, 129.6, 129.5,
129.0, 128.7, 127.1, 126.8, 123.3, 121.1, 116.1, 115.2, 114.0, 48.9;
IR (neat): 3442, 3361, 3205, 3011, 1620, 1511, 1311, 1170, 1074,
811, 554, 527, 447 cmꢂ1; HRMS (ESI-TOF) m/z calcd for
1184, 1107, 831, 815, 603, 567 cmꢂ1
.
4-((2-Aminophenyl)(4-aminophenyl)methyl)phenol (4f). 10%
yield (0.0296 g) as a brown solid; mp: 184–186 ꢀC; Rf ¼ 0.48 (50%
1
EtOAc/n-hexane); H-NMR (400 MHz, DMSO-d6): d 9.20 (s, 1H),
6.89 (td, J ¼ 7.2, 1.6 Hz, 1H), 6.83 (d, J ¼ 8.4 Hz, 2H), 6.70 (d, J ¼
8.4 Hz, 2H), 6.65 (d, J ¼ 8.4 Hz, 2H), 6.60 (dd, J ¼ 8.0, 0.8 Hz,
1H), 6.53 (dd, J ¼ 7.6, 1.2 Hz, 1H), 6.50–6.44 (m, 3H), 5.16 (s,
1H), 4.89 (brs, 2H), 4.49 (brs, 2H); 13C-NMR (100 MHz, DMSO-
d6): d 155.5, 146.8, 145.5, 134.0, 130.4, 130.0, 129.5, 129.0, 129.0,
126.5, 116.1, 115.0, 114.9, 113.9, 49.2; IR (neat): 3369, 3302,
3018, 2923, 2853, 2807, 2684, 2612, 1894, 1713, 1609, 1508,
1489, 1453, 1242, 1175, 1158, 1103, 1013, 939, 866, 834, 819,
797, 752, 707, 640, 626, 549, 527, 447 cmꢂ1; HRMS (ESI-TOF) m/z
calcd for C19H17N2O [M ꢂ H]ꢂ 289.1346, found 289.1334.
4-(Bis(4-aminophenyl)methyl)-2-methoxyphenol (3g).13a CAS
number 114163-79-0; 82% yield (0.2620 g) as a brown solid; mp:
160–162 ꢀC; Rf ¼ 0.23 (50% EtOAc/n-hexane); 1H-NMR (400
MHz, DMSO-d6): d 8.71 (s, 1H), 6.71 (d, J ¼ 8.4 Hz, 4H), 6.64 (d, J
¼ 8.4 Hz, 1H), 6.61 (d, J ¼ 2.0 Hz, 1H), 6.45 (d, J ¼ 8.4 Hz, 4H),
6.40 (dd, J ¼ 8.4, 2.0 Hz, 1H), 5.05 (s, 1H), 4.85 (s, 4H), 3.63 (s,
3H); 13C-NMR (100 MHz, DMSO-d6): d 147.2, 146.4, 144.4, 136.7,
132.5, 129.3, 121.2, 115.0, 113.7, 113.33, 113.31, 55.6, 54.2; IR
C
19H18N3O2 [M + H]+ 320.1394, found 320.1394.
4,40-((2,4-Dichlorophenyl)methylene)dianiline (3d).6r CAS
number 2451434-53-8; 85% yield (0.2915 g) as a yellow oil; Rf ¼
0.42 (40% EtOAc/n-hexane);1-NMR (400 MHz, DMSO-d6): d 7.54
(d, J ¼ 2.4 Hz, 1H), 7.33 (dd, J ¼ 8.4, 2.0 Hz, 1H), 6.92 (d, J ¼
8.4 Hz, 1H), 6.64 (d, J ¼ 8.4 Hz, 4H), 6.47 (d, J ¼ 8.4 Hz, 4H), 5.46
(s, 1H), 3.95 (brs, 4H); 13C-NMR (100 MHz, DMSO-d6): d 147.0,
142.2, 134.1, 132.0, 131.2, 129.6, 129.5, 128.7, 127.0, 113.9, 51.0;
IR (neat): 3443, 3355, 3210, 2924, 1727, 1619, 1510, 1465, 1274,
1045, 819, 573, 508 cmꢂ1
2-((4-Aminophenyl)(2,4-dichlorophenyl)methyl)aniline (4d).
10% yield (0.0340 g) as a white solid; mp: 120–122 ꢀC; Rf ¼ 0.56
(40% EtOAc/n-hexane); 1H-NMR (400 MHz, DMSO-d6): d 7.57 (d,
J ¼ 2.0 Hz, 1H), 7.34 (dd, J ¼ 8.4, 2.0 Hz, 1H), 6.94 (td, J ¼ 8.0,
1.2 Hz, 1H), 6.85 (d, J ¼ 8.4 Hz, 1H), 6.72–6.65 (m, 3H), 6.51 (d, J
¼ 8.4 Hz, 2H), 6.47 (td, J ¼ 7.2, 0.8 Hz, 1H), 6.39 (dd, J ¼ 7.6,
1.2 Hz, 1H), 5.48 (s, 1H), 5.01 (s, 2H), 4.52 (s, 2H); 13C-NMR (100
MHz, DMSO-d6): d 147.4, 145.6, 140.8, 134.5, 131.8, 131.6, 129.8,
128.9, 128.4, 127.3, 127.1, 127.0, 126.2, 116.3, 115.4, 114.1, 46.9;
(neat): 3005, 2971, 1738, 1366, 1216 cmꢂ1
.
© 2021 The Author(s). Published by the Royal Society of Chemistry
RSC Adv., 2021, 11, 22692–22709 | 22699