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1,2-Dinitrobenzene is one of three isomers of dinitrobenzene, with the formula C 6 H 4 (NO 2) 2. The compound is a white or colorless solid that is soluble in organic solvents. It is prepared from 2-nitroaniline by diazotization and treatment with sodium nitrite in the presence of a copper catalyst. [1]
The three possible arrangements of the nitro groups afford three isomers, 1,2-dinitrobenzene, 1,3-dinitrobenzene, and 1,4-dinitrobenzene. Each isomer has the chemical formula C 6 H 4 N 2 O 4 and a molar mass of about 168.11 g/mol. 1,3-Dinitrobenzene is the most common isomer and it is used in the manufacture of explosives.
In contrast, 2-methyl-1,4-dinitrobenzene (2c) is isolated in only 9.9% yield. [4] As witnessed in the above example, when a π-acceptor substituent (πAS) is meta to a π-donor substituent (πDS), the electrophilic aromatic nitration occurs ortho to the πAS rather than para.
The gauche effect is very sensitive to solvent effects, due to the large difference in polarity between the two conformers.For example, 2,3-dinitro-2,3-dimethylbutane, which in the solid state exists only in the gauche conformation, prefers the gauche conformer in benzene solution by a ratio of 79:21, but in carbon tetrachloride, it prefers the anti conformer by a ratio of 58:42. [9]
2,4-Dinitrochlorobenzene (DNCB) is an organic compound with the chemical formula (O 2 N) 2 C 6 H 3 Cl. It is a yellow solid that is soluble in organic solvents . It is an intermediate for the industrial production of other compounds.
Nitrobenzenes are a group of nitro compounds consisting of one or more nitro groups as substituents on a benzene core. They have the formula C 6 H 6–n (NO 2) n, where n = 1–6 is the number of nitro groups. Depending on the number of nitro groups, there may be several constitutional isomers possible. Mononitrobenzene; Dinitrobenzene. 1,2 ...
1,3-Dinitrobenzene is accessible by nitration of nitrobenzene. The reaction proceeds under acid catalysis using sulfuric acid. The directing effect of the nitro group of nitrobenzene leads to 93% of the product resulting from nitration at the meta-position. The ortho- and para-products occur in only 6% and 1%, respectively. [1]
Ball-and-stick model of a 1,2-dinitrobenzene molecule, C 6 H 4 N 2 O 4, also known as ortho-dinitrobenzene or o-dinitrobenzene. The molecule is shown as found in the crystal structure reported in Acta Crystallogr. B (1990) 46, 567–572 and CSD entry ZZZFYW01. Colour code: Carbon, C: grey Hydrogen, H: white Nitrogen, N: blue