ChemicalBook CAS DataBase List 2-Nitrochlorobenzene

2-Nitrochlorobenzene synthesis

11synthesis methods

Product Name:2-Nitrochlorobenzene
CAS Number:88-73-3
Molecular formula:C6H4ClNO2
Molecular Weight:157.55

Nitration of chlorobenzene with mixed acid (30/56/14) typically gives an isomer mix in 98 % yield consisting of 34 – 36 % 2-Nitrochlorobenzene, 63 – 65 % 4- chloronitrobenzene, and only ca. 1 % 3- chloronitrobenzene. The ortho – para ratio of about 0.55 is in sharp contrast to the 1.6 obtained with nitrotoluene isomers. As with the nitration of toluene, much work has been done on isomer control so that the producer might have some flexibility towards the balance of isomer demand. Although no major change in ratio has been achieved, the situation is better for nitrochlorobenzene than nitrotoluenes, because the favored isomer is in much greater demand. In further contrast to the nitration of toluene, the nitration of chlorobenzene in the presence of phosphoric acid decreases the proportion of 4-Nitrochlorobenzene, and the use of phosphoric acid in the presence of a transition-metal catalyst is said to increase the ortho – para ratio to ca. 0.8.

88-72-2
249 suppliers
$15.00/25g

88-73-3
8 suppliers
$16.00/25g

Yield:88-73-3 86.1%

Reaction Conditions:

with bromine;iodine;chlorine at 140; for 2 h;Reagent/catalyst;Temperature;

Steps:

32 Example 32
In a 1000 ml four-necked round bottom flask, 312.56 g o-nitrotoluene and a quantitative catalyst (a mixture of 10: 1 mass ratio of bromine and elemental iodine) were added. The mass ratio of o-nitrotoluene to the catalyst was controlled at1: 0.08,235r / min speed stirring and heated to 140 ° C, slowly into the chlorine gas, two hours after the sample, with gas chromatography tracking reaction by-products o-nitrobenzylidene chloride to 5%O-nitrotoluene conversion of 41%, the reaction was stopped; After completion of the reaction, the degree of vacuum -0.098MPa, vacuum distillation at a temperature of 109 deg.] C, recovering nitrotoluene, continued use of chlorinated cyclic;The residue after recovery of o-nitrotoluene was recrystallized from petroleum ether to obtain o-nitrochlorobenzyl chloride as a white crystalline solid.
In this example, the production effect of 99.2% of o-nitrochlorobenzyl chloride and 86.1% of yield (based on the actual consumed o-nitrotoluene) was achieved.

References:

Sichuan Fusida Biotechnology Development Co., Ltd.;Liu, Hu;Wang, Wen;Ma, Qingwei;Chen, Xi;Li, Zhou;Zhang, Hua;Wang, Lei CN106008348, 2016, A Location in patent:Paragraph 0119; 0120