Category: 16588-26-4

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《o-Halogenated p-nitroaniline and its derivatives》. Authors are Korner, G.; Contardi.The article about the compound:3-Bromo-4-chloronitrobenzenecas:16588-26-4,SMILESS:BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl).Product Details of 16588-26-4. Through the article, more information about this compound (cas:16588-26-4) is conveyed.

When p-NO2C6H4NH2 is dissolved or suspended in HCl and Cl or Br added a mixture, difficult to sep., of mono- and dihalogenated anilines with the halogen in the o-position is formed. If, however, gaseous Cl (mol. ratio 1 : 1) is passed into the b. HCl solution 2,4-Cl(O2N)C6H3NH2 is almost the sole product. This derivative mixed with some di-Cl derivative is obtained on chlorinating at -o°(Casella & Co., Ger. Pat., 109,189). At room temperature, on adding Cl slowly to the HCl solution, the di-Cl deriv, + quinone are formed. Chlorinating by Noelting’s method, using Ca(ClO)2, gave mixtures Similar results were obtained with Br. These derivatives are obtained by warming 1-nitro-3,4-dibromo (or dichloro) benzene with alc. NH3 in the scaled tube at 190°. The NH2 group substitutes p to NO2. By halogenating these monohalogen derivatives it is possible to get derivatives with 2 different halogens in the same ring. The action of ClI on a glac. AcOH solution of p-NO2C6H4NH2 gives mixtures from which the mono- and di-I derivatives can be separated by EtOH. 1-Nitro-3-chloro-4-aniline, bright yellow needles from hot H2O, m. 104.5°; acetyl derivative, straw-yellow flat prisms from EtOH, m. 139°. Diazotizing in H2SO4 or HNO3 suspension with gaseous HNO2 gives the diazo compound which, by way of the perbromide, goes into 1-nitro-3-chloro-4-bromobenzene, prisms from CHCl2, m. 62°. 1-Nitro-3-chloro-4-iodobenzene, almost colorless needles from EtOH, m. 103°, is obtained similarly, by way of the periodide. 1-Nitro-3-bromo-4-aniline, bright yellow needles, m. 104.5°, which with Ac2O gives the monoacetyl derivative, flat prisms, m. 114°, and the diacetyl derivative, short fat prisms, m. 132°. also from the mono derivative, by the action of Ac2O + traces of POCl3. Diazotizing and halogenating as above gives 1-nitro-3-bromo-4-chlorobenzene, white or colorless prisms, volatil with steam, m. 61°, is identical with the compound similarly obtained from 2,5-Cl(O2N)C6H3NH2. 1-Nitro-3-bromo-4-iodobenzene, prisms from AcOEt, m. 106°, was obtained similarly. 1-Nitro-3-iodo-4-aniline presents 2 forms: (1) stable yellow-red prisms, and (2) the labile forms golden yellow plates in C6H6, below 17°, m. 109°; monoacetyl derivative, bright yellow prisms; diacetyl derivative, more soluble than the mono compound, white needles. The diazo compound, on adding Cl, gives 1-nitro-3-iodo-4-chlorobenzene, needles, m. 78°, identical with the compound obtained similarly with I from 2,5-Cl(O2N)C6H2NH2. 1-Nitro-3,5-dichloro-4-aniline, yellow shining needles, m. 195°, slightly soluble in dilute and concentrate inorganic acids, unchanged by fuming HNO3 in the cold. To diazotize suspend in HNO3 (d. 1.38) and add gaseous HNO2 at o°; on diluting the explosive diazonium nitrate seps., fairly soluble in H2O. Ac2O + traces of POCl3 give the monoacetyl derivative, almost colorless needles, m. 215°, and the diacetyl derivative, monoclinic (Artini, Rend. ist. lombardo sci. lett., [2] 45, 1912), prisms, m. 142.5°, d. 1.565, more soluble than the mono compound In absolute EtOH + some concentrate H2SO4 + EtONO it gives 1-nitro-3,5-dichlorobenzene, plates, m. 65.4°, which on reducing with Sn + HCl gives 3,5-dichloroaniline, needles, m. 51.5°. The latter, by replacing NH3 with Cl, gives 1,3,4-trichlorobenzene, white needles, to. 63.5°, which is also obtained from 2,4,6-Cl3C8H2NH2, m. 77.5°, by replacing NH3, with H. 3,5-Cl2C4H3NH2 by replacing NH2 with Br gave 1-bromo-3,5-dichlorobenzene, needles, m. 75.8°. 1-Iodo-3,5-dichlorobenzene, m. 54°, was obtained similarly and is identical with that prepared similarly from 2,4,6-ICl2C6H2NH2, m. 84°. Anilines containing 3 identical halogen ats. in the 2,4,6-positions may be obtained by direct halogenation of PhNH2 of which they are the end products. The mixed halogenated anilines are made from anilines halogenated in p-position by adding two halogens (Br or ClI) in the o-position in glac. AcOH. o,p- or o,o-dihalogenanilines may even be used, but displacing of weak halogens may take place. All of the theoretically possible trihalogenbenzenes can be obtained by thus substituting halogen for NH2 in anilines. 2,6,4-Cl2(O2N)C6H2NH2 gives 1-nitro-3,4,5-trichlorobenzene, bright yellow prisms, m. 72.5°, volatil with steam; reduction and elimination of NH2 gives 1,2,3-C6H2Cl3, identical with that from 2,6-Cl2C6H3NH2 by the same method. 1-Nitro-3,5-dichloro-4-bromobenzene, from the above aniline, yellow. prisms, m. 88°, volatile with steam; similarly 1-nitro-3,5-dichloro-4-iodobenzene, yellow prisms, m. 154.8°, less volatile; reduction, etc., gives 1,3-dichloro-2-iodobenzene, thin plates, m. 68°, volatile with steam, also from 3,6-C;2C4H3NH2 with I. p-NO3 C4H4NH2 + Br gives 1-nitro-3,5-dibromo-4-aniline, yellow plates, m. 202.5°; Ac2O as above gives the monoacetyl derivative, colorless needles or triclinic prisms, isomorphous with the di-Cl compound, and the diacetyl derivative, prisms, m. 136°, triclinic pinacoidal, a : b : c = 1.0901 : 1 : 0.8325, a = 88° 43′ 4”. β = 70° 49′ 34”. γ = 93° 25′ 39”, d. 1.939.3 Diazotizing the above or 2,4.6-Br2(O2N)C5H2NH3 with EtONO, etc., gives 1-nitro-3,5-dibromobenzene, almost colorless needles, m. 104.5°; on reduction with Sn + HCl, etc., it gives sym.-dibromochlorobenzene, m. 119°, with Cl, or dibromoiodobenzene, m. 124.8°, with 1. Both are easily volatil with steam and may be prepared from the corresponding anilines and the latter also from 2,4,6-IBr2C6H2NH2. 1-Nitro-3,4,5-tribromobenzene, from the o,o-dibromoaniline by replacing NH3 with Br, yellowish prisms, m. 111.9° on reduction, etc., gives 1,2,3-C6H3Br3, m. 87.8°. 1-Nitro-3,5-dibromo-4-chlorobenzene from the same aniline, yellowish prisms, m. 92-7°, on reduction, etc., gives 2,6-Br2C6H3Cl, m. 71°, identical with the compound similarly obtained from 2,6-Br2C6H3NH2 by replacing NH2 with Cl. 1-Nitro-3,5-dibromo-4-iodobenzene, from 2,6,4-Br2(O2N)C6H2NH2, prisms, 135.5°, cannot be reduced to the aniline. The 2,6-Br2C6H2I was obtained from 2,6-Br2C6H3NH2, prisms, m. 72°. 1-Nitro-3,5-diiodo-4-aniline, from p-NO2C6H4NH2 + ClI in AcOH, yellow needles; m. 245°; monoacetyl derivative, yellow needles, m. 249°; diacetyl derivative, paler yellow prisms, m. 171°, triclinic pinacoidal, a : b : c = 0.9682 : 1 : O.7260, α = 83° 6’43”, β = 76°8’29”, γ = 99° 42′ 44”, d. 2.290. 1-Nitro-3,5-diiodobenzene, from the preceding, difficultly volatile with steam, yellowish prisms, m. 104.5°, on reducing with FeSO4 + NH3 gives 3,5-I2C6H2NH3, needles, m. 110°. 2,6,4-I2ClC6H2NH2 gave 1,3-diiodo-5-chlorobenzene, needles, m. 101°, discolors brown in the light. Similarly the 5-bromoaniline gave 1,3-diiodo-5-bromobenzene, m. 140°, slightly volatile with steam. 1,3,5-Triiodobenzene, from 2,4,6-I2C6H2NH2 or 3.5-I2C6H3NH2, opaque needle, m. 184.2°. Decompose of 2,6,4-I2(O2N)C6H2N2NO3 with b. aqueous Cu2Cl2 gave 1-nitro-3,5-diiodo-4-chlorobenzene, needles, m. 110°; reduction with FeSO4 + NH3 gives a poor yield, (NH4)2S gives a better yield of the aniline together with some S-containing compound The aniline gives 2,6-I2C6H3Cl, rhombic plates, m. 82°. 2,6,4-I2(O2N)(C6H2NH2 gives 1-nitro-3,5-diiodo-4-bromobenzene, white needles from EtOH, yellow prisms from CHCl3 m. 125.4°, and 1-nitro-3,4,5-triiodobenzene, yellow prisms from EtOH, contain C6H6 of crystallization when crystallized from C6H6; reduction with FeSO4 + NH3 gives 3,4,5-triiodoaniline with difficulty; (NH4)2S gives sym.-I2C6H2NH2. The I2C6H2NH2 gives 1,2,3-C6H2I2 on changing NH2 for H, m. 116°, which is identical with that from 2,3-I2C6H3NH2. 2,4-Cl(O2N)C6H3NH2 + Br gives 1-nitro-3-chloro-5-bromo-4-aniline, bright Yellow needles, m. 177.4°; monoacetyl derivative, straw-yellow needles, m. 224°; diacetyl derivative, prisms or plates, m. 139°, monoclinic, prismatic, a : b : c = 1.1127 : 1 : 0.8509, β = 70-36°, d. 1-749. 1-Nitro-3-chloro-5-bromobenzene, from the above aniline, plates, m. 81.2°. and this on reducing with Sn + HCl, etc., gives 3-chloro-5-bromoaniline, needles, or prisms. The latter, as well as 2,4,6-BrClIC6H2NH2, m. 110.5°, gives 1-chloro-3-bromo-5-iodobenzene, needles, m. 85.8°. 1-Nitro-3,4-dichloro-5-bromobenzene, yellowish prisms, m. 82.5°, 1-Nitro-3,4-dibromo-5-chlorobenzene, yellowish prisms, m. 99.5°, and 1-nitro-3-chloro-4-iodo-5 bromobenzene, needles, 159°, by replacing NH2 with a halogen in the preceding nitroaniline. 1,2-Dibromo-3-chlorobenzene, by reducing 3,4,5-Br2ClC6H2NO2, rhombic plates. m. 72.6°. 2,4-Cl(O2N)C6H2NH22, in HOAc + ClI gives 1-nitro-3-chloro-5-iodo-4-aniline, bright yellow needles, 195°; monoacetyl derivative, white prisms, m. 207°; diacetyl derivative, prisms, m. 113°, monoclinic, a : b : c = 1.038 :-1 : 0.799, β = 71.44°, d. 1.913. This aniline gives 1-nitro-3-chloro-5-iodobenzene, yellow prisms, m. 70.4° by replacing NH2 with Cl. 1-Nitro-3,4-dichloro-5-iodobenzene, from the aniline with Cl, bright yellow prisms, m. 59°, is not easily reduced by FeSO4 + NH3, but Sn + HCl gives 3,5-CHC6H3NH2, plates, m. 69.8°; with Br the aniline gives 1-nitro-3-chloro-4-bromo-5-iodobenzene, almost colorless needles, m. 95°; and with I it gives 1-nitro-3-chloro-4,5-diiodobenzene, almost colorless needles, m. 146.5°. 3,4,5-Cl2IC6H2NO2 + (NH4)2S in EtOH gives 3,4-Cl2C6H3NH2. 2,4-Br(O2N)C6H3NH2 + CH in HOAc gives 1-nitro-3-bromo-5-iodo-4-aniline, needles, m. 221°; monoacetyl derivative, yellowish prisms, m. 226°; diacetyl derivative, prisms, m. 134°, triclinic pinacoidal, a : b : C = 0.9470 : 1 : 0.7288, α = 83° 59′ 54”, β = 77° 30′ 18”, γ = 99° 6′ 14”, d.2.112. 1-Nitro-3-bromo-5-iodobenzene, by replacing NH2 with H in the preceding aniline, needles, m. 97.5°; 1-nitro-3-bromo-4-chloro-5-iodobenzene, by replacing NH2 with Cl, yellowish prisms or colorless needles, m. 84°.

If you want to learn more about this compound(3-Bromo-4-chloronitrobenzene)Product Details of 16588-26-4, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(16588-26-4).

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 3-Bromo-4-chloronitrobenzene, is researched, Molecular C6H3BrClNO2, CAS is 16588-26-4, about Optimization of pyrimidinyl- and triazinyl-amines as non-nucleoside inhibitors of HIV-1 reverse transcriptase.Quality Control of 3-Bromo-4-chloronitrobenzene.

Non-nucleoside inhibitors of HIV-1 reverse transcriptase are being pursued through synthesis and assaying for anti-viral activity. Following computational analyses, the focus has been on the motif Het-NH-Ph-U, where Het is an aromatic heterocycle and U is an unsaturated, hydrophobic group. Previous investigations with Het = 2-thiazoyl and 2-pyrimidinyl are extended here to triazinyl derivatives The result is several NNRTIs in the 2-20 nM range with negligible cytotoxicity and auspicious predicted pharmacol. properties.

If you want to learn more about this compound(3-Bromo-4-chloronitrobenzene)Quality Control of 3-Bromo-4-chloronitrobenzene, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(16588-26-4).

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 3-Bromo-4-chloronitrobenzene(SMILESS: BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl,cas:16588-26-4) is researched.Recommanded Product: Dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer. The article 《Synthesis of phenothiazines via ligand-free CuI-catalyzed cascade C-S and C-N coupling of aryl ortho-dihalides and ortho-aminobenzenethiols》 in relation to this compound, is published in Chemical Communications (Cambridge, United Kingdom). Let’s take a look at the latest research on this compound (cas:16588-26-4).

A ligand-free CuI-catalyzed cascade C-S and C-N cross coupling of (hetero)aryl ortho-dihalides and ortho-aminobenzenethiols has been developed, and various phenothiazines were synthesized with excellent regioselectivity. A possible mechanism is proposed for the cascade coupling.

Here is a brief introduction to this compound(16588-26-4)SDS of cas: 16588-26-4, if you want to know about other compounds related to this compound(16588-26-4), you can read my other articles.

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 16588-26-4, is researched, Molecular C6H3BrClNO2, about Structure-activity relationships for chemical and glutathione S-transferase-catalyzed glutathione conjugation reactions of a series of 2-substituted 1-chloro-4-nitrobenzenes, the main research direction is glutathione transferase catalyzed conjugation chloronitrobenzene MSBAR; structure activity relationship glutathione transferase isoenzyme.HPLC of Formula: 16588-26-4.

Glutathione S-transferases (GSTs) constitute an important class of phase II (de)toxifying enzymes, catalyzing the conjugation of glutathione (GSH) with electrophilic compounds In the present study, Km, kcat and kcat/Km values for the rat GST 1-1-, 3-3-, 4-4- and 7-7-catalyzed conjugation reactions between GSH and a series of 10 different 2-substituted 1-chloro-4-nitrobenzenes, and the second-order rate constants (ks) of the corresponding base-catalyzed reactions, were correlated with nine classical physico-chem. parameters (electronic, steric and lipophilic) of the substituents and with 16 computer-calculated mol. parameters of the substrates and of the corresponding Meisenheimer complexes with MeS- as a model nucleophile for GS- (charge distributions and several energy values), giving structure-activity relationships. On the basis of an identical dependence of the base-catalyzed as well as the GST 1-1- and GST 7-7-catalyzed reactions on electronic parameters (among others, Hammett substituent constant σp and charge on p-nitro substituents), and the finding that the corresponding reactions catalyzed by GSTs 3-3 and 4-4 depend to a significantly lesser extent on these parameters, it was concluded that the Mu-class GST isoenzymes have a rate-determining transition state in the conjugation reaction between 2-substituted 1-chloro-4-nitrobenzenes and GSH which is different from that of the other two GSTs. Several alternative rate-limiting transition states for GST 3-3 and 4-4 are discussed. Furthermore, based on the obtained structure-activity relationships, it was possible to predict the kcat/Km values of the four GST isoenzymes and the ks of the base-catalyzed GSH conjugation of 1-chloro-4-nitrobenzene.

Here is a brief introduction to this compound(16588-26-4)HPLC of Formula: 16588-26-4, if you want to know about other compounds related to this compound(16588-26-4), you can read my other articles.

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 16588-26-4, is researched, Molecular C6H3BrClNO2, about Synthesis and study of trichinellocidal activity of some bromine and chlorine derivatives of 8-quinolyloxysalicylanilides, the main research direction is quinolyloxysalicylanilide preparation trichinosis inhibition; trichinellocidal salicylanilide quinolyloxy preparation; Trichinella infestation quinolyloxysalicylanilide anthelmintics preparation.Application of 16588-26-4.

Some title derivatives were synthesized and tested for trichinellocidal activity. N-[3-bromophenyl-4-(5-chloroquinolinoxy)]-3,5-dibromosalicylamide exhibited trichinellocidal activity (in mice infected with decapsulated Trichinella spiralis) that was close to that of mebendazole.

Here is a brief introduction to this compound(16588-26-4)Application of 16588-26-4, if you want to know about other compounds related to this compound(16588-26-4), you can read my other articles.

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 16588-26-4. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 3-Bromo-4-chloronitrobenzene, is researched, Molecular C6H3BrClNO2, CAS is 16588-26-4, about Continuous Flow Nucleophilic Aromatic Substitution with Dimethylamine Generated in Situ by Decomposition of DMF. Author is Petersen, Trine P.; Larsen, Anders F.; Ritzen, Andreas; Ulven, Trond.

A safe, practical, and scalable continuous flow protocol for the in situ generation of dimethylamine from DMF followed by nucleophilic aromatic substitution of a broad range of aromatic and heteroaromatic halides is reported.

Here is a brief introduction to this compound(16588-26-4)Application of 16588-26-4, if you want to know about other compounds related to this compound(16588-26-4), you can read my other articles.

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 3-Bromo-4-chloronitrobenzene(SMILESS: BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl,cas:16588-26-4) is researched.Application In Synthesis of 2-Bromomethyl-1,3-dioxolane. The article 《Structurally Simple Inhibitors of Lanosterol 14α-Demethylase Are Efficacious In a Rodent Model of Acute Chagas Disease》 in relation to this compound, is published in Journal of Medicinal Chemistry. Let’s take a look at the latest research on this compound (cas:16588-26-4).

We report structure-activity studies of a large number of dialkyl imidazoles as inhibitors of Trypanosoma cruzi lanosterol-14α-demethylase (L14DM). The compounds have a simple structure compared to posaconazole, another L14DM inhibitor that is an anti-Chagas drug candidate. Several compounds display potency for killing T. cruzi amastigotes in vitro with values of EC50 in the 0.4-10 nM range. Two compounds were selected for efficacy studies in a mouse model of acute Chagas disease. At oral doses of 20-50 mg/kg given after establishment of parasite infection, the compounds reduced parasitemia in the blood to undetectable levels, and anal. of remaining parasites by PCR revealed a lack of parasites in the majority of animals. These dialkyl imidazoles are substantially less expensive to produce than posaconazole and are appropriate for further development toward an anti-Chagas disease clin. candidate.

There is still a lot of research devoted to this compound(SMILES：BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl)Category: alcohols-buliding-blocks, and with the development of science, more effects of this compound(16588-26-4) can be discovered.

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called In Situ Synthesized Silica-Supported Co@N-Doped Carbon as Highly Efficient and Reusable Catalysts for Selective Reduction of Halogenated Nitroaromatics, published in 2020-09-15, which mentions a compound: 16588-26-4, Name is 3-Bromo-4-chloronitrobenzene, Molecular C6H3BrClNO2, Recommanded Product: 3-Bromo-4-chloronitrobenzene.

Silica-supported Co@N-doped carbon (Co@CN/SiO2) catalysts were first prepared by a one-step impregnation with a mixed solution of cobalt nitrate, glucose and urea, followed by in situ carbonization and reduction The Co@CN/SiO2 catalysts were investigated for the selective reduction of nitro aromatics RNO2 (R = Ph, 4,5-dichloro-2-nitroaniline, 2-chloro-3-nitropyridine, etc.) to the corresponding anilines RNH2 using hydrazine hydrate. The Co@CN/SiO2-500 carbonized at 500°C exhibited the highest catalytic activity and excellent stability without any decay of activity after 6 cycles for the reduction of nitrobenzene. Both metallic Co atoms and Co-N species formed in the Co@CN/SiO2 catalysts were active, but the Co-N species were dominant active sites. The high activities of the Co@CN/SiO2 catalysts were attributed to the synergistic effect between the Co and N atoms, promoting heterolytic cleavage of hydrazine to form H+/H- pairs. Representative examples demonstrated that the Co@CN/SiO2-500 could completely transform various halogen-substituted nitro aromatics to the corresponding halogenated anilines with high TOFs and selectivity of >99.5%.

There is still a lot of research devoted to this compound(SMILES：BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl)Recommanded Product: 3-Bromo-4-chloronitrobenzene, and with the development of science, more effects of this compound(16588-26-4) can be discovered.

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Nuclear-substituted derivatives of 4,4′-diaminodiphenyl sulfone》. Authors are Berg, S. S..The article about the compound:3-Bromo-4-chloronitrobenzenecas:16588-26-4,SMILESS:BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl).Quality Control of 3-Bromo-4-chloronitrobenzene. Through the article, more information about this compound (cas:16588-26-4) is conveyed.

The therapeutic effect of (4-H3NC6H4)3SO3 prompted the investigation of the halogen derivatives; these were tested orally in vivo against Staphylococcus aureus and Streptococcus pyogenes in mice; a decrease in toxicity in the order Cl < Br < iodine, together with corresponding decrease in activity, was observed 2,4-Br(O2N)C6H3NH2 (18.5 g.), through the diazo reaction, gives 12.5 g. 1-chloro-2-bromo-4-nitrobenzene, b0.1 100°, m. 61°. p-O2NC6H4SH (1.55 g.) and 0.4 g. NaOH in 20 cc. EtOH, added to 1.9 g. 3,4-Cl2C6H3NO2 in 10 cc. EtOH and refluxed 2 h., give 1.3 g. 2-chloro-4,4'-dinitrodiphenyl sulfide (I), yellow, m. 144°; the 2-Br analog, yellow, m. 159°, and the 2-I analog, yellow, m. 168°. 3,4-Cl2C6H3NO2 (15 g.) in 60 cc. EtOH, treated (5 min.) with 10 g. Na2S.9H2O in 40 cc. 25% aqueous EtOH and refluxed 6 h., gives 7.2 g. [2,4-Cl(O2N)C6H3]2S, yellow, m. 163°; the portion (3 g.) insoluble in 95% AcOH is the compound C24H12O5N4Cl4S2, probably RN(→O):NR, where R = 3,4-Cl[2,4-Cl(O2N)C6H3S]C6H3S-, red, m. 195°. 2,2'-Diiodo-4,4'-dinitrodiphenyl sulfide (II), pale red, m. 186°. 2,4-Br(O2N)C6H3OH yields an acetate (III), pale yellow, m. 86°; 13 g. III, 7.8 g. p-O2NC6H4SH, 3 g. K2CO3, and 100 cc. Me2CO, refluxed 2 h., yield 6 g. 4,4'-dinitro-2-acetoxydiphenyl sulfide (IV), yellow, m. 100°. Dropwise addition of 7.5 g. KMnO4 in 50 cc. hot H2O to 10 g. I in 150 cc. boiling AcOH gives 8 g. 2-chloro-4,4'-dinitrodiphenyl sulfone (V), m. 182-3°; 2-Br analog, m. 162°, 2-I analog, pale yellow, m. 165°; the sulfone from II, yellow, m. 260°. IV yields 4,4'-dinitro-2-hydroxydiphenyl disulfone, yellow, m. 216°. Reduced Fe (10 g.), added slowly to 5 g. V in 200 cc. boiling AcOH and the mixture heated 10 min. at 90°, gives 3 g. 2-chloro-4,4'-diaminodiphenyl sulfone, pale yellow, m. 114°; 2-Br analog, yellow, m. 157°; 2-I analog, buff, m. 207°. 2,2'-Dichloro-4,4'-diaminodiphenyl sulfone, orange, m. 263°; 2,2'-di-I analog, m. 280°. 4,4'-Diamino-2-hydroxydiphenyl sulfone, m. 134-5° [sulfate, m. 208° (decomposition)] (cf. Burton and Hoggarth, C.A. 39, 4854.7). There is still a lot of research devoted to this compound(SMILES：BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl)Quality Control of 3-Bromo-4-chloronitrobenzene, and with the development of science, more effects of this compound(16588-26-4) can be discovered.

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Journal of Organic Chemistry called Continuous Flow Nucleophilic Aromatic Substitution with Dimethylamine Generated in Situ by Decomposition of DMF, Author is Petersen, Trine P.; Larsen, Anders F.; Ritzen, Andreas; Ulven, Trond, which mentions a compound: 16588-26-4, SMILESS is BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl, Molecular C6H3BrClNO2, Formula: C6H3BrClNO2.

A safe, practical, and scalable continuous flow protocol for the in situ generation of dimethylamine from DMF followed by nucleophilic aromatic substitution of a broad range of aromatic and heteroaromatic halides is reported.

There is still a lot of research devoted to this compound(SMILES：BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl)Formula: C6H3BrClNO2, and with the development of science, more effects of this compound(16588-26-4) can be discovered.

Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts