Molecules 2016, 21, 1042
9 of 13
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N-(4-Methoxyphenyl)-benzenemethanamine (3ad). CAS: 17377-95-6; Pale yellow oil; Yield: 91%. H-NMR
(300 MHz, CDCl3, 25 ˝C)
7.40 (d, J = 7.3 Hz, 2H), 7.30 (t, J = 6.3 Hz, 2H), 7.00 (dd, J = 5.3, 2.5 Hz,
2H), 6.83 (d, J = 5.7 Hz, 1H), 6.74 (d, J = 7.6 Hz, 2H), 4.35 (s, 2H), 4.02 (bs, 1H), 3.90 (s, 3H) 13C-NMR
(75 MHz, CDCl3, 25 ˝C)
158.9, 148.3, 131.5, 129.3 (2C), 129.3 (2C), 117.6, 114.1 (2C), 112.9 (2C), 55.4,
47.9 MS (m/z) 213 (100), 198 (9), 168 (5), 136 (9), 122 (97), 91 (89), 77 (6), 65 (14), 51 (4).
δ
δ
1
N-(4-Chlorophenyl)-benzenemethanamine (3ae). CAS: 2948-37-0; Pale yellow oil; Yield: 88%. H-NMR
(300 MHz, CDCl3, 25 ˝C)
δ 7.35 (d, J = 4.5 Hz, 2H), 7.34–7.25 (m, 3H), 7.11 (d, J = 8.9 Hz, 2H), 6.55 (d,
J = 8.9 Hz, 2H), 4.31 (s, 2H), 4.07 (bs, 1H). 13C-NMR (75 MHz, CDCl3, 25 ˝C) 145.3, 138.0, 129.28 (2C),
128.9 (2C), 127.9 (2C), 127.6, 123.7, 115.2 (2C), 49.3. MS (m/z) 217 (40), 140 (7), 111 (6), 91 (100), 65 (9),
51 (3).
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N-(4-Fluorophenyl)-benzenemethanamine (3af). CAS: 370-77-4; Pale yellow oil; Yield: 92 %. H-NMR
(300 MHz, CDCl3, 25 ˝C)
δ 7.43–7.27 (m, 5H), 6.97–6.84 (m, 2H), 6.63–6.53 (m, 2H), 4.31 (s, 2H), 3.94
˝
(s, 1H). 13C-NMR (75 MHz, CDCl3, 25 C)
δ
157.8 (s), 154.7 (s), 143.8 (s), 138.7 (s), 128.7 (s), 127.6
(JCF = 18.1 Hz), 115.9 (s), 115.6 (s), 114.3 (JCF = 7.5 Hz), 77.5 (s), 77.1 (s), 76.7 (s), 49.3 (s). MS (m/z) 201
(53), 124 (9), 91 (100), 65 (10), 51 (3).
1
N-(3-Fluorophenyl)-benzenemethanamine (3ag). CAS: 123330-53-0; Pale yellow oil; Yield: 87%. H-NMR
(300 MHz, CDCl3, 25 ˝C)
6.34–6.31(m, 1H), 4.32 (s, 2H), 4.18 (s, 1H). 13C-NMR (75 MHz, CDCl3, 25 ˝C)
δ
7.37–7.36 (m, 4H), 7.32–7.28 (m, 1H), 7.12–7.08 (m, 1H), 6.41–6.39 (m, 2H),
164.4 ( CF = 241 Hz),
δ
J
150.1 (JCF = 11Hz), 139.0, 130.5 (JCF = 10 Hz), 129.0, 127.7, 127.6, 109.0, 104.2 (JCF = 21 Hz), 99.7
(JCF = 25 Hz), 48.4. MS (m/z) 201 (52), 124 (8), 91 (100), 65 (16), 51 (5).
N-(3,4-Dichlorophenyl)-benzenemethanamine (3ah). CAS: 51597-75-2; Pale yellow oil; Yield: 94%. 1H-NMR
(300 MHz, CDCl3, 25 ˝C)
δ 7.44–7.26 (m, 1H), 7.18 (d, J = 8.7 Hz, 1H), 6.71 (d, J = 2.7 Hz, 1H), 6.46
˝
(dd, J = 8.7, 2.8 Hz, 1H), 4.29 (s, 1H), 4.23 (s, 1H). 13C-NMR (75 MHz, CDCl3, 25 C) 147.6, 138.4, 132.9,
130.7, 128.9 (2C), 127.7, 127.5 (2C), 120.2, 114.1, 112.7, 48.3. MS (m/z) 251 (27), 174 (4), 145 (4), 91 (100),
65 (8), 51 (2).
1
N-(3,5-Dichlorophenyl)-benzenemethanamine (3ai). CAS: 65089-00-1; Pale yellow oil; Yield: 87%. H-NMR
(300 MHz, CDCl3, 25 ˝C)
δ
7.47 – 7.32 (m, 5H), 6.72 (t, J = 1.7 Hz, 1H), 6.53 (d, J = 1.7 Hz, 2H), 4.35 (s,
1H), 4.33 (s, 2H). 13C-NMR (75 MHz, CDCl3, 25 ˝C)
δ
140.8, 136.1, 129.6, 128.6 (2C), 127.6, 126.9 (2C),
123.2, 120.2, 113.4, 48.2. MS (m/z) 251 (27), 174 (4), 145 (4), 91 (100), 65 (8), 51 (2).
N-(3-Chloro-4-fluorophenyl)-benzenemethanamine (3aj). CAS: 131776-32-4; Pale yellow oil; Yield: 97%.
1H-NMR (300 MHz, CDCl3, 25 ˝C)
δ 7.36–7.26 (m, 4H), 7.24–7.20 (m, 1H), 7.06 (t, J = 9.2 Hz,1H), 6.63
(dd, J = 2.8, 6.4 Hz, 1H), 6.51 (dt, J = 3.2, 9.2 Hz, 1H), 6.43 (t, J = 5.8 Hz, 1H), 4.22 (s, 2H, J = 6.0 Hz).
˝
13C-NMR (75 MHz, CDCl3, 25 C) 153.2, 146.2, 146.1, 138.7, 128.9, 128.7, 127.8, 127.6, 127.6, 117.0, 113.9,
112.1, 48.0. MS (m/z) 235 (32), 158 (5), 129 (6), 91 (100), 65 (8), 51 (2).
N-(4-(Trifluoromethyl)phenyl)-benzenemethanamine (3ak). CAS: 405-81-2; Pale yellow oil; Yield: 76%.
˝
1H-NMR (300 MHz, CDCl3, 25 C)
δ
7.49–7.16 (m, 6H), 7.02–6.90 (m, 1H), 6.86 (m, 1H), 6.76 (dd, J = 8.2
,
2.3 Hz, 1H), 4.35 (s, 2H), 1.54 (s, 1H). 13C-NMR (75 MHz, CDCl3, 25 ˝C)
δ
150.6, 138.6, 128.9, 127.6,
127.5, 126.8, 123.7, 119.2 (q, JCF = 32.5 Hz), 48.0. MS (m/z) 251 (42), 174 (7), 145 (11), 91 (100), 65 (8),
51 (2).
N-(Phenylmethyl)-benzenemethanamine (3am). CAS: 103-49-1; Pale yellow oil; Yield: 93%. 1H-NMR
(300 MHz, CDCl3, 25 ˝C)
25 ˝C)
91 (100), 77 (6), 65 (14), 51 (5).
δ
7.61–7.29 (m, 10H), 3.93 (s, 4H), 1.76 (s, 1H). 13C-NMR (75 MHz, CDCl3,
140.4 (2C), 128.4 (4C), 128.2 (4C), 127.0 (2C), 53.2 (2C). MS (m/z) 196 (14), 120 (8), 106 (57),
δ
1
N-Hexylben˝zenemethanamine (3an). CAS: 25468-44-4; Pale yellow oil; Yield: 88%. H-NMR (300 MHz,
CDCl3, 25 C)
δ 7.47–7.22 (m, 5H), 3.84 (s, 2H), 2.67 (t, J = 9.3 Hz, 2H), 1.64–1.29 (m, 6H), 0.94 (t,