RSC Advances
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ARTICLE
DOI: 10.1039/C5RA01915J
layer was dried over anhydrous sodium sulphate (Na2SO4). Then the m/z 481 (M+), Anal. Calcd for C18H12NBr3: C, 44.84; H, 2.49; N,
solvent was evaporated in vacuo, the products were purified using 2.91%. Found: C, 44.32; H, 2.31; N, 2.89%.
silica column chromatography by normal hexane to afford
4-Bromo- N,N-bis (phenyl)aniline (3h). White solid. 1H NMR (400
triarylamines.
MHz, CDCl3): δ (ppm) 7.01 (d, 2H), 7.16 (m, 6H), 7.22 (d, 4H), 7.42
(d, 2H). 13C NMR (100 MHz, CDCl3): δ (ppm) 115.35, 120.64,
4.4. Spectral data for Triarylamine derivatives
124.97, 127.79, 128.44, 136.21, 146.69, 147.74. FTꢀIR (KBr): 3085,
1590, 1483, 1273, 1075 cmꢀ1.
1
Triphenylamine (3a). White solid. H NMR (400 MHz, CDCl3): δ
(ppm) 7.08 (m, 9H), 7.26 (d, 6H), 13C NMR (100 MHz, CDCl3): δ
4-Bromo- N,N-bis (4-methylphenyl)aniline (3i). Yellowish solid.
1H NMR (400 MHz, CDCl3): δ (ppm) 2.35 (s, 6H), 6.92 (d, 2H),
7.01 (d, 4H), 7.09 (d, 4H), 7.31 (d, 2H). 13C NMR (100 MHz,
CDCl3): δ (ppm) 19.96, 113.07, 124.88, 126.34, 129.52, 132.65,
135.06, 145.84, 146.37. FTꢀIR (KBr): 3110, 2989, 1568, 1495, 1275,
1069 cmꢀ1.MS (EI, 70 eV): m/z 350 (M+), Anal. Calcd for
C20H18NBr: C, 68.20; H, 5.11; N, 3.98%. Found: C, 68.08; H, 4.96;
N, 3.73%.
(ppm) 124.82, 125.46, 135.62, 147.65. FTꢀIR (KBr): 3031, 3016,
1590, 1454, 1276 cmꢀ1. MS (EI, 70 eV): m/z 244 (M+), Anal. Calcd
for C18H15N: C, 88.16; H, 6.12; N, 5.72%. Found: C, 87.95; H, 6.01;
N, 5.62%.
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N,N-bis (4-bromophenyl)aniline (3b). Colorless viscous liquid. H
NMR (400 MHz, CDCl3): δ (ppm) 6.95 (d, 4H), 7.06 (m, 3H), 7.27
(d, 2H), 7.35 (d, 4H). 13C NMR (100 MHz, CDCl3): δ (ppm) 115.53,
123.82, 124.66, 125.46, 129.62, 132.22, 146.57, 146.96. FTꢀIR
(KBr): 3071, 3056, 1579, 1484, 1274, 1070 cmꢀ1. MS (EI, 70 eV):
m/z 400 (M+), Anal. Calcd for C18H13NBr2: C, 53.87; H, 3.24; N,
3.50%. Found: C, 53.61; H, 3.03; N, 3.35%.
4-Bromo- N,N-bis (2-methoxyphenyl)aniline (3j). Yellowish solid.
1H NMR (400 MHz, CDCl3): δ (ppm) 3.64 (s, 6H), 7.01 (d, 2H),
7.12 (m, 4H), 7.21 (m, 4H), 7.31 (d, 2H). 13C NMR (100 MHz,
CDCl3): δ (ppm) 61.54, 120.32, 122.64, 125.49, 129.18, 132.78,
135.63, 136.13, 145.22, 146.39, 150.79. FTꢀIR (KBr): 3051, 2964,
1598, 1422, 1265, 1049 cmꢀ1.MS (EI, 70 eV): m/z 383 (M+), Anal.
Calcd for C20H18NO2Br: C, 62.52; H, 4.69; N, 3.65%. Found: C,
62.43; H, 4.49; N, 3.51%.
1
4-Methyl- N,N-bis (4-bromophenyl)aniline (3c). White solid. H
NMR (400 MHz, CDCl3): δ (ppm) 2.32 (s, 3H), 6.91 (d, 4H), 6.96
(d, 2H), 7.09 (d, 2H), 7.31 (d, 4H). 13C NMR (100 MHz, CDCl3): δ
(ppm) 20.89, 114.94, 124.92, 125.20, 130.25, 132.23, 133.86,
144.29, 146.69. FTꢀIR (KBr): 3033, 2922, 1578, 1483, 1276, 1070
cmꢀ1. MS (EI, 70 eV): m/z 415 (M+), Anal. Calcd for C19H15NBr2: C,
54.70; H, 3.60; N, 3.36%. Found: C, 54.63; H, 3.49; N, 3.28%.
4-Bromo- N,N-bis (3-methoxyphenyl)aniline (3k). Yellow solid.
1H NMR (400 MHz, CDCl3): δ (ppm) 3.75 (s, 6H), 6.98 (m, 4H),
7.02 (m, 3H), 7.09 (m, 3H), 7.24 (d, 2H). 13C NMR (100 MHz,
CDCl3): δ (ppm) 61.89, 112.21, 119.82, 124.46, 125.97, 130.52,
132.79, 134.23, 135.17, 145.91, 148.64, 155.01. FTꢀIR (KBr): 3064,
2922, 1581, 1462, 1272, 1081 cmꢀ1. MS (EI, 70 eV): m/z 382 (M+),
Anal. Calcd for C20H18NO2Br: C, 62.52; H, 4.69; N, 3.65%. Found:
C, 62.41; H, 4.56; N, 3.48%.
2-Methoxy- N,N-bis (4-bromophenyl)aniline (3d). White solid. 1H
NMR (400 MHz, CDCl3): δ (ppm) 3.69 (s, 3H), 6.93 (d, 4H), 7.01
(d, 1H), 7.12 (m, 3H), 7.32 (d, 4H). 13C NMR (100 MHz, CDCl3): δ
(ppm) 56.48, 115.45, 122.32, 124.92, 125.65, 129.25, 132.03,
132.86, 145.12, 145.97. FTꢀIR (KBr): 3031, 2935, 1585, 1472, 1272,
1072 cmꢀ1. MS (EI, 70 eV): m/z 430 (M+), Anal. Calcd for
C19H15NOBr2: C, 52.68; H, 3.47; N, 3.23%. Found: C, 52.51; H,
3.38; N, 3.21%.
4-Bromo- N,N-bis (4-methoxyphenyl)aniline (3l). Yellow solid. 1H
NMR (400 MHz, CDCl3): δ (ppm) 3.81 (s, 6H), 6.98 (d, 2H), 7.21
(d, 4H), 7.28 (d, 2H), 7.43 (d, 4H). 13C NMR (100 MHz, CDCl3): δ
(ppm) 59.36, 115.07, 124.48, 133.97, 134.58, 138.27, 146.19,
147.41, 152.63. FTꢀIR (KBr): 3088, 2921, 1579, 1475, 1277, 1073
cmꢀ1. MS (EI, 70 eV): m/z 383 (M+), Anal. Calcd for C20H18NO2Br:
C, 62.52; H, 4.69; N, 3.65%. Found: C, 62.35; H, 4.51; N, 3.49%.
1
3-Methoxy- N,N-bis (4-bromophenyl)aniline (3e). White solid. H
NMR (400 MHz, CDCl3): δ (ppm) 3.72 (s, 3H), 6.90 (s, 1H), 6.94
(d, 4H), 7.05 (m, 3H), 7.22 (d, 4H). 13C NMR (100 MHz, CDCl3): δ
(ppm) 57.84, 116.14, 120.21, 121.85, 124.36, 131.51, 133.97,
142.65, 144.84, 152.23. FTꢀIR (KBr): 3033, 2950, 1523, 1454, 1256,
1064 cmꢀ1. MS (EI, 70 eV): m/z 431 (M+), Anal. Calcd for
C19H15NOBr2: C, 52.68; H, 3.47; N, 3.23%. Found: C, 52.57; H,
3.32; N, 3.24%.
1
4-Methyl- N,N-bis (4-nitrophenyl)aniline (3m). Yellow solid. H
NMR (400 MHz, DMSOꢀd6): δ (ppm) 2.31 (s, 3H), 7.16 (d, 2H),
7.18 (d, 4H), 7.33 (d, 2H), 8.05 (d, 4H). 13C NMR (100 MHz,
DMSOꢀd6): δ (ppm) 21.36, 122.34, 125.36, 126.27, 130.58, 132.60,
139.04, 147.23, 147.69. FTꢀIR (KBr): 3063, 3043, 1548, 1508, 1452,
1335, 1273 cmꢀ1. MS (EI, 70 eV): m/z 348 (M+), Anal. Calcd for
C19H15N3O4: C, 65.32; H, 4.33; N, 12.03%. Found: C, 65.06; H,
4.12; N, 12.15%.
1
4-Methoxy- N,N-bis (4-bromophenyl)aniline (3f). White solid. H
NMR (400 MHz, CDCl3): δ (ppm) 3.75 (s, 3H), 6.90 (d, 2H), 6.96
(d, 4H), 7.08 (d, 2H), 7.39 (d, 4H). 13C NMR (100 MHz, CDCl3): δ
(ppm) 57.98, 115.34, 126.34, 131.50, 133.73, 135.65, 145.67,
146.32, 150.07. FTꢀIR (KBr): 3056, 2948, 1584, 1457, 1273, 1075
cmꢀ1. MS (EI, 70 eV): m/z 431 (M+), Anal. Calcd for C19H15NOBr2:
C, 52.68; H, 3.47; N, 3.23%. Found: C, 52.54; H, 3.35; N, 3.19%.
4-Methyl- N,N-bis (4-carbomethoxy)aniline (3n). Yellow solid. 1H
NMR (400 MHz, DMSOꢀd6): δ (ppm) 2.35 (s, 3H), 3.61 (s, 6H),
7.06 (d, 2H), 7.21 (d, 4H), 7.32 (d, 2H), 7.94 (d, 4H). 13C NMR (100
MHz, DMSOꢀd6): δ (ppm) 20.05, 60.21, 121.43, 126.54, 127.78,
130.08, 132.52, 138.41, 147.35, 147.74, 167.49. FTꢀIR (KBr): 3061,
3045, 1735, 1542, 1503, 1459, 1332, 1271 cmꢀ1. MS (EI, 70 eV):
4-Bromo- N,N-bis 4-bromophenyl)aniline (3g). Pale green solid.
1H NMR (400 MHz, CDCl3): δ (ppm) 6.97 (d, 6H), 7.08 (d, 6H). 13
C
NMR (100 MHz, CDCl3): δ (ppm) 115.23, 125.92, 132.43, 146.59.
FTꢀIR (KBr): 3056, 1585, 1483, 1272, 1071 cmꢀ1. MS (EI, 70 eV):
6 | J. Name., 2012, 00, 1-3
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