ChemicalBook CAS DataBase List 4-Chloro-2-nitrotoluene

4-Chloro-2-nitrotoluene synthesis

14synthesis methods

Product Name:4-Chloro-2-nitrotoluene
CAS Number:89-59-8
Molecular formula:C7H6ClNO2
Molecular Weight:171.58

4-Chlorotoluene is nitrated with mixed acid (39/59/2) at 25 ℃ to give a mixture of 4-Chloro-2-nitrotoluene (65 %) and 4-Chloro-3-nitrotoluene (35 %) isomers. The major component is separated as the lower boiling fraction on vacuum distillation. 4-Chloro-3-nitrotoluene [89-60-1] can be obtained, if required, from the residue by distillation and sweating.

106-43-4
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$14.00/5g

89-59-8
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$23.00/25g

Yield:89-59-8 49.2%

Reaction Conditions:

with sulfuric acid;nitric acid in water at 50 - 55; for 2 h;

Steps:

9 4.5.9 4-Chloro-1-methyl-2-nitrobenzene (9)

H₂O (3.3mL) was dispersed in 4-chlorotoluene (39.5mmol) and whilst stirring the mixture of 65% HNO₃ (3.0mL) and 96% H₂SO₄ (13.2mL) was added drop wise at the temperature 50-55°C. Then, the reaction mixture was stirred at 55°C for 2h, H₂O (50mL) was added and the mixture was extracted three times with CHCl₃ (50mL). The organic phases were collected, dried over Na₂SO₄ and purified by column chromatography. Yield: 49.2%, yellow-white solid; mp: 37-38°C; IR: 1556 ( CC aromatic), 1521 (_as NO₂), 1481, 1451 ( CC aromatic), 1347 (_s NO₂) cm^-1; ¹H NMR (CDCl₃, 300MHz): δ 7.96 (1H, d, J=2.2Hz, H3), 7.47 (1H, dd, J=8.2Hz, J=2.2Hz, H5), 7.29 (1H, d, J=8.2Hz, H6), 2.57 (3H, s, CH₃); ¹³C NMR (CDCl₃, 75MHz): δ 149.35, 133.81, 133.01, 132.39, 132.02, 124.67, 19.95.