Specific features of nucleophilic substitution in 1-chloro-3,4-dinitrobenzene

Zotova, Natalia; Kushakova, P. M.; Кузнецов, В. А.; Rodin, A. A.; Гарабаджиу, А. В.

doi:10.1007/s11178-005-0043-z

Cited by 5 publications

(2 citation statements)

References 2 publications

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“…The following nitroanilines were obtained according to the published procedures: 1a [15], 1b [15], 1c [12f], 1d [16], 1j [17], 1 k [18], and 1o [12d]. Nitroanilines 1i and 1l were commercial.…”

Section: General Informationmentioning

confidence: 99%

Synthesis of various 1‐alkylbenzimidazole derivatives directly from 2‐alkylaminonitroarenes via a two‐step, one‐pot procedure

Walewska‐Królikiewicz,

Wilk,

Kwast

et al. 2024

Journal of Heterocyclic Chem

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N‐Alkyl‐2‐nitroanilines deoxygenated with tributylphosphine form intermediate 2‐(alkylamino)aryliminophosphoranes, which were subjected, without isolation, to various cyclocondensation reactions with CS2, CO2, alkyl isocyanates, acyl chlorides, anhydrides, or esters. A simple, convenient, one‐pot procedure provided derivatives of unsymmetrically substituted 1‐alkylbenzimidazoles functionalized at C2 in good to excellent yields. The method does not require the use of metals, sensitive catalysts, or pressure.

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Section: General Informationmentioning

confidence: 99%

Synthesis of various 1‐alkylbenzimidazole derivatives directly from 2‐alkylaminonitroarenes via a two‐step, one‐pot procedure

Walewska‐Królikiewicz,

Wilk,

Kwast

et al. 2024

Journal of Heterocyclic Chem

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“…Halopolynitroarenes are an important class of organic synthesis intermediates, which can introduce various substituents through S N Ar reaction, in which, depending on the degree of activation, both nitro groups and halogen atoms can be replaced. − 1,5-Dichloro-2,4-dinitrobenzene (DCDNB) is a common halopolynitroarenes, which can be used to synthesize a variety of dyes and many diverse sensitive high-energy materials. , It can also synthesize 4,6-diaminoresorcinol and then synthesize a ultra-high-performance fiber, poly [ (benzo [ 1,2- d :5,4- d ′] bisoxazole-2,6-diyl)-1,4-henylene] …”

Section: Introductionmentioning

confidence: 99%

Solubility Measurement and Correlation of 1,5-Dichloro-2,4-Dinitrobenzene in 15 Pure Solvents at Temperatures from 298.15 to 333.15 K

Liu

Zhang

et al. 2022

J. Chem. Eng. Data

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This study reports the solubility of 1,5-dichloro-2,4-dinitrobenzene (DCDNB) in 15 pure solvents [methanol, ethanol, i-propanol, n-butanol, methylbenzene, methylene chloride, trichloromethane, tetrachloromethane, ethylene dichloride, acetone, ethyl ethanoate, ethanenitrile, N-methyl-2-pyrrolidone (NMP), dimethylformamide (DMF), and dimethyl sulfoxide (DMSO)] determined by the laser dynamic method at a temperature ranging from 298.15 to 333.15 K at 0.1 MPa. The solubility of DCDNB in all selected solvents showed an increasing trend with increasing temperature. In addition, the descending order of DCDNB solubility at 298.15 K is NMP > DMF > acetone > methylbenzene > DMSO > ethyl ethanoate > methylene chloride > ethylene dichloride > ethanenitrile > trichloromethane > tetrachloromethane > methanol > ethanol > n-butanol > i-propanol. The solvent effect was studied by the KAT-LSER model, which showed that the Hildebrand solubility parameter of solvents had a great effect on the solubility of DCDNB. Four models were used to correlate the experimental solubility data, including the modified Apelblat model, van't Hoff model, λh model, and NRTL model, which showed that the modified Apelblat model gave the best correlation, and the largest relative average deviation and root-mean-square deviation were no more than 3.54 × 10 −2 and 2.97 × 10 −3 , respectively.

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