P- Chloronitrobenzene

The suggestion outlined above about the way in which through-conjugation influences the nitration of p-chloronitrobenzene is relevant to the observed reactivities (ortho > meta > para) of the isomeric chloronitrobenzenes. Application of the additivity principle to the... 

An ortho nitro group exerts a comparable rate enhancing effect m Chloronitrobenzene although much more reactive than chlorobenzene itself is thousands of times less reac tive than either o or p chloronitrobenzene... 

The idea that hydrogen bonding, as a special ortho effect of the substrate, may be involved in the transition state of the reactions with amines was first proposed by Chapman et al. Attempting to test this hypothesis, Hawthorne investigated the hydrogen-isotope effect in the reaction of o- and p-chloronitrobenzene with... 

Para-for 4-j Mononitrophenol Yellowish monocl prismatic crysts mp 113—14° bp 279 de-compn d 1.479—1.495 at 20°. Can be prepd from p-chloronitrobenzene. Sol in hot w, ale eth. Most toxic of the three isomers by ingestion and inhalation... 

C H4CIN02 88-73-3) see Amoxapine Clemizole Domperidone Olanzapine Quetiapine fumarate p-chloronitrobenzene... 

Wu J-F, C-W Sun, C-Y Jiang, Z-P Liu, S-J Liu (2005) A novel 2-aminophenol 1,6-dioxygenase involved in the degradation of p-chloronitrobenzene by Comamonas strain CNB-1 purification, properties, genetic cloning and expression in Escherichia coli. Arch Microbiol 183 1-8. 

FIGURE 2.37 Decrease in rate of hydrogenation of p-chloronitrobenzene with decrease in particle size. 

Vicarious nucleophilic substitution of nitroarenesThe carbanion (2, NaOCH,) of 1 reacts with p-chloronitrobenzene to give, after acidic workup, 5-chloro-2-nitrobenzyl p-tolylsulfone (3). The reagent 2 is typical of a number of carbanions which can undergo nucleophilic substitution ortho or para to nitro-... 

Figure 1. Best-fitted conversion (%)/time (min) curves for the PEG-8000 mediated fluoroalkoxylation of 0-, m- and p-chloronitrobenzenes...

TRINITROBENZENE m-DIBROMOBENZENE m-CHLORONITROBENZENE o-CHLORONITROBENZENE p-CHLORONITROBENZENE tn-D I CHLOROBENZENE o-DICHLOROBENZENE p-DI CHLOROBENZENE m-DIFLUOROBENZENE o-DIFLUOROBENZENE p-DIFLUOROBENZENE m-DI NITROBENZENE o-DINITROBENZENE p-DINITROBENZENE BROMOBENZENE MONOCHLOROBENZENE m-CHLOROPHENOL o-CHLOROPHENOL p-CHLOROPHENOL... 

Biological. Under aerobic conditions, the yeast Rhodosporidium sp. metabolized p-chloronitrobenzene to 4-chloroacetanilide and 4-chloro-2-hydroxyacetanilide as final major metabolites, intermediate compounds identified include 4-chloronitrosobenzene, 4-chlorophen-ylhydroxylamine, and 4-chloroaniline (Corbett and Corbett, 1981). 

Under continuous flow conditions involving feeding, aeration, settling, and reflux, a mixture of jD-chloronitrobenzene and 2,4-dinitrochlorobenzene was reduced 61-70% after 8-13 d by Arthrobacter simplex, a microorganism isolated from industrial waste. A similar experiment was conducted using two aeration columns. One column contained A. simplex, the other a mixture of A. simplex and microorganisms isolated from soil Streptomyces coelicolor, Fusarium sp., probably aquaeductum and Trichoderma viride). After 10 d, 89.5-91% of the nitro compounds was reduced. p-Chloronitrobenzene was reduced to 4-chloroaniline and six unidentified compounds (Bielaszczyk et al., 1967). 

Photolytic. An aqueous solution containing p-chloronitrobenzene and a titanium dioxide (catalyst) suspension was irradiated with UV light ilk >290 nm). 2-Chloro-5-nitrophenol was the only compound identified as a minor degradation product. Continued irradiation caused additional degradation yielding carbon dioxide, water, hydrochloric and nitric acids (Hustert et al., 1987). 

Chemical. Although no products were identified, p-chloronitrobenzene (1.5 x 10 M) was reduced by iron metal (33.3 g/L acid washed 18-20 mesh) in a carbonate buffer (1.5 x 10 M) at pH 5.9 and 15 °C. Based on the pseudo-first-order disappearance rate of 0.0336/min, the half-life was 20.6 min (Agrawal and Tratnyek, 1996). 

---