2213-82-3

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 267, 1979 DOI: 10.1021/jo01316a024

InChI:InChI=1/C6H2Cl2N2O4/c7-3-1-4(9(11)12)6(8)5(2-3)10(13)14/h1-2H

Upstream product

• 106-46-7 para-dichlorobenzene 
• 88-87-9 4-chloro-2,6-dinitrophenol 
• 98-59-9 p-toluenesulfonyl chloride 
• 99-65-0 meta-dinitrobenzene 
• 618-86-0 1-chloro-3,5-dinitrobenzene 
• 89-61-2 2,5-dichloronitrobenzene 
• 106-48-9 4-chloro-phenol 
• 71-43-2 benzene 
• 606-21-3 1-chloro-2,6-dinitrobenzene 
• 5388-62-5 4-chloro-2,6-dinitroaniline 

Downstream Products

• 5388-62-5 4-chloro-2,6-dinitroaniline 
• 6302-58-5 2,6-dinitro-4-chloroanisole 
• 68151-90-6 dimethyl-dithiocarbamic acid-(4-chloro-2,6-dinitro-phenyl ester) 
• 88-87-9 4-chloro-2,6-dinitrophenol 
• 32831-41-7 2,5-dichloro-1,3-phenylenediamine 
• 857595-86-9 2,5-dichloro-3-nitro-aniline 
• 89581-79-3 (4-chloro-2,6-dinitro-phenyl)-hydrazine 
• 10156-68-0 4-chloro-N,N-dimethyl-2,6-dinitroaniline 
• 39522-55-9 1-Nitro-3-chlorphenoxazin 
• 91268-10-9 6-chloro-4-nitro-2-phenyl-2H-benzotriazole 
• 56205-36-8 3-(4-chloro-2,6-dinitro-phenyl)-2-thioxo-thiazolidin-4-one 
• 68142-47-2 5-benzylidene-3-(4-chloro-2,6-dinitro-phenyl)-2-thioxo-thiazolidin-4-one 
• 68142-31-4 3-(4-chloro-2,6-dinitro-phenyl)-5-(4-methoxy-benzylidene)-2-thioxo-thiazolidin-4-one 
• 16771-05-4 2'-Brom-,4-chlor-2,6-dinitro-diphenylsulfid 

Relevant academic research and scientific papers

Synthesis of 6-aminobenzopentathiepines by reactions of 4-nitrobenzodithiol-2-ones with NaHS

The reactions of benzodithiol-2-ones containing a 4-nitro group with NaHS led to mixtures of 6- aminobenzopentathiepines and 4-nitrobenzotrithiols. The product ratio and yields depend on the substituent in the aromatic ring. Based on the yields of benzopentathiepines, the following series of substituent efficiency can be inferred: CF3 ? F, Cl > CN. Aminobenzopentathiepines are probably formed via the intermediate benzotrithiols; the transformation apparently starts with the reduction of the nitro group.

Improved method for preparing 1-amino-3,7,8-trichlorodibenzo-p-dioxin

An improved method was proposed for preparing 1-amino-3,7,8-trichlorodibenzo-p-dioxin.

Metabolism and disposition of 1,4,7,8-tetrachlorodibenzo-p-dioxin in rats

Metabolism studies of 1,4,7,8-tetrachlorodibenzo-p-dioxin (TCDD), a relatively nontoxic dioxin congener, were undertaken to gain a better understanding of mammalian metabolism of dioxins without the problems associated with the use of the most toxic congener, 2,3,7,8-TCDD. 14C- 1,4,7,8-TCDD was dosed to conventional and bile-cannulated rats at a level of 8 mg/kg. The 14C was excreted almost entirely in 72 hours with the major routes of excretion feces and bile. Metabolites were identified from the feces, bile, and urine by GC-MS or negative ion FAB MS and 1H NMR. The two major fetal metabolites were hydroxylated tetra- and triCDDs. Glucuronide and sulfate conjugates of these hydroxyl metabolites were found in the urine and bile. Minor metabolites included dichlorocatechol, dihydroxylated tetra- and triCDDs, and conjugates of these compounds.

Electrophilic Aromatic Substitution. Part 35. Chlorination of 1,3-Dinitrobenzene, 1-Chloro-2,4-dinitrobenzene, and 2,4-Dinitrotoluene with Nitric Acid and Hydrogen Chloride or Chlorine in Sulphuric Acid or Oleum

Solutions of sulphuric acid or oleum containing HCl or Cl2 and nitric acid have been found both to chlorinate and nitrate deactivated aromatic compounds.The kinetics and products of the chlorination of 1,3-dinitrobenzene and 1-chloro-2,4-dinitrobenzene in sulphuric acid or oleum containing HCl and nitric acid at 130 deg C, and the kinetics and products of the chlorination of 2,4-dinitrotoluene at 90 deg C in sulphuric acid or oleum containing Cl2 and nitric acid, are reported. 1,3-Dinitrobenzene and 1-chloro-2,4-dinitrobenzene were predominantly chlorinated. 2,4-Dinitrotoluene gave approximately equal amounts of 6-chloro-2,4-dinitrotoluene and 2,4,6-trinitrotoluene.The results show that under these conditions, chlorination and nitration are competing electrophilic reactions, and that chlorination is less selective than nitration.Possible mechanisms for chlorination are discussed.

Electrophilic Aromatic Substitution. Part 34. Nitration of 1-Chloro-4-nitrobenzene, 1,3-Dichloro-2-nitrobenzene, 1,3-Dinitrobenzene, 1-Chloro-2,4-dinitrobenzene, and 2-Chloro-1,3-dinitrobenzene in Sulphuric Acid and Oleum

Yields of the expected nitro products from 1-chloro-4-nitrobenzene and 1,3-dichloro-2-nitrobenzene nitrated at 25 deg C in sulphuric acid or oleum containing 1 mol dm-3 nitric acid were quantitative.The rate profile for nitration of 1,3-dichloro-2-nitrobenzene is normal, but sulphonation is a competing process when the concentration of nitric acid is low.Kinetics of nitration of 1,3-dinitrobenzene at 150 deg C are reported; yields of 1,3,5-trinitrobenzene, the only detected aromatic product, are low.The title chlorodinitrobenzenes each give, on nitration at 130 deg C, a dichlorodinitrobenzene as well as a chlorotrinitrobenzene.The kinetics and yields of the two products from 1-chloro-2,4-dinitrobenzene under a variety of conditions are reported and discussed in relation to a previously proposed mechanism.

Electrophilic Aromatic Substitution. Part 33. Kinetics and Products of Aromatic Nitrations in Solutions of Dinitrogen Pentaoxide in Nitric Acid

The kinetics and/or products of reaction, in nitric acid containing 0-5 mol dm-3 of dinitrogen pentaoxide, of phenyltrimethylammonium perchlorate, 1,2-dichloro-4-nitrobenzene, 2,4-dinitrotoluene, 1,4-dichloro-2-nitrobenzene, 1,2,4-trichloro-5-nitrobenzene, 1,2,4,5-tetrachlorobenzene, pentachlorobenzene, 1,2,3-trichlorobenzene, 1,3,5-trichloro-2-nitrobenzene, 1,2-dichloro-3-nitrobenzene, 1,2,3,4-tetrachlorobenzene, and 1,3-dichloro-2-nitrobenzene, have been studied.For each substrate investigated kinetically, rate coefficients for nitration in solutions containing more than ca. 2 mol dm-3 dinitrogen pentaoxide increase more quickly than the concentration of nitronium ion.In the cases of 1,2,4,5-tetrachlorobenzene, 1,4-dichloro-2-nitrobenzene, and 1,2,4-trichloro-5-nitrobenzene, but not with the other substrates, there was evidence for the formation of, in addition to expected aromatic nitroproducts, unstable cyclohexadiene products.Those from 1,2,4-trichloro-5-nitrobenzene were identified as a diastereomeric pair of 3,5,6-trichloro-2,4-dinitrocyclohexa-2,5-dienyl nitrates.A mechanism for the formation of these products is proposed.