ChemicalBook CAS DataBase List 4-Nitro-3-trifluoromethyl aniline

4-Nitro-3-trifluoromethyl aniline synthesis

10synthesis methods

Product Name:4-Nitro-3-trifluoromethyl aniline
CAS Number:393-11-3
Molecular formula:C7H5F3N2O2
Molecular Weight:206.12

The thiazolium salt 3 (3.30 mg, 0.0122 mmol) was added to a solution of 1-azido-4-nitrobenzene (0.122 mmol) and t-BuOH (18.0 mg, 0.244 mmol) in degassed THF (0.50 mL) under argon at r.t. The resulting suspension was stirred for 5 min, and then NaOt-Bu (23.4 mg, 0.244 mmol) was added in one portion, and the mixture was stirred (Table 2). Water (2 mL) was added, and the products were extracted with EtOAc (2 × 2 mL), the combined organic phase was dried over anhyd MgSO4, filtered, and concentrated in vacuo. Purification was achieved by passing the resulting residue through a short pad of silica (eluting with 50% light PE-EtOAc) unless otherwise stated.
4-Nitro-3-trifluoromethyl aniline, Time: 12 h, Pale yellow solid (21.0 mg, 84%). (70:30 petrol-EtOAc) 0.5; mp 90-93 °C (lit., 92-93 °C); IR (FTIR, CHCl3) νmax cm-1: 3535 (NH2), 3434 (NH2), 1635, 1592 (NO2), 1520 (NO2), 1119; 1H NMR (400 MHz, DMSO-6) 8.59 (d, = 2.7 Hz, 1H), 8.55 (dd, = 9.3, 2.7 Hz, 1H), 7.55 (br s, 2H), 7.32 (d, = 9.3 Hz, 1H); 13C NMR (100 MHz, DMSO-6) 151.8 (C), 135.0 (C), 128.7 (CH), 123.7 (J = 5.9 Hz, F3N2NaO2 [M+Na]+, 229.0195; found, 229.0195.

Fig. The synthetic of 4-Nitro-3-trifluoromethyl aniline

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393-11-3
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Yield:-

Steps:

Multi-step reaction with 2 steps
1: HNO₃, H₂SO₄
2: aq. H₂SO₄

References:

Forbes,E.J. et al. [Tetrahedron,1960,vol. 8,p. 67 - 72]

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References

13311-84-7
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393-09-9 Synthesis

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References

Benzene, 4-azido-1-nitro-2-(trifluoromethyl)-

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References

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