65078-77-5

Usage

Uses

Used in Dye and Pigment Production:
2,3-dichloro-6-nitroaniline is utilized as a key intermediate in the synthesis of dyes and pigments, contributing to the coloration and stability of these products in various applications.
Used in Pharmaceutical Synthesis:
2,3-dichloro-6-nitroaniline also serves as an intermediate in the production of pharmaceuticals, where its chemical properties are harnessed to create active ingredients for medications.
Used in Organic Compound Synthesis:
2,3-dichloro-6-nitroaniline is employed in the synthesis of other organic compounds, highlighting its versatility in organic chemistry and its ability to be a building block for a range of chemical products.

InChI:InChI=1/C6H4Cl2N2O2/c7-3-1-2-4(10(11)12)6(9)5(3)8/h1-2H,9H2

Upstream product

• 6327-47-5 2,3-dichloroformanilide 
• 17700-09-3 4-nitro-1,2,3-trichlorobenzene 
• 7664-41-7 ammonia 
• 23068-36-2 N-(2,3-dichlorophenyl)-acetamide 
• 87-61-6 1,2,3-trichlorobenzene 
• 608-27-5 2,3-dichloroaniline 
• 99-54-7 3,4-dichloronitrobenzene 
• 65078-76-4 2,3-dichloro-6-nitroacetanilide 

Downstream Products

• 1668-01-5 3,4-dichloro-1,2-phenylenediamine 
• 717108-60-6 2-chloro-3-morpholino-6-nitroaniline 
• 74070-47-6 2-Chloro-3-phenylthio-6-nitroaniline 
• 2262452-06-0 3-[1-(6,7-dichloro-1H-benzimidazol-2-yl)-5-hydroxy-3-methyl-pyrazol-4-yl]-3H-isobenzofuran-1-one 
• 74070-46-5 aclonifen 
• 95-76-1 m,p-dichloroaniline 
• 173461-08-0 1-(2-Benzyloxy-1-benzyloxymethyl-ethoxymethyl)-2,4,5-trichloro-1H-benzoimidazole 
• 173460-82-7 1-(2-Benzyloxy-ethoxymethyl)-2,4,5-trichloro-1H-benzoimidazole 
• 173460-79-2 2-bromo-4,5-dichlorobenzimidazole 
• 1378864-94-8 1,2-diamino-3-chloro-4-methoxybenzene 
• 717108-61-7 3-chloro-4-morpholino-1,2-diaminobenzene 
• 89975-38-2 2-chloro-3-methoxy-6-nitroaniline 
• 65078-76-4 2,3-dichloro-6-nitroacetanilide 
• 20039-23-0 1,2-dichloro-3,4-dinitrobenzene 

Relevant academic research and scientific papers

Preparation method of 3, 4-dichloro-2-fluoroaniline

The invention discloses a preparation method of 3, 4-dichloro-2-fluoroaniline, which comprises the following steps: (1) taking 1, 2, 3-trichlorobenzene as a raw material, and carrying out nitration reaction to obtain 2, 3, 4-trichloronitrobenzene; (2) the 2, 3, 4-trichloronitrobenzene is subjected to an ammonolysis reaction, and 2, 3-dichloro-6-nitroaniline is obtained; (3) carrying out diazotization reaction on the 2, 3-dichloro-6-nitroaniline, fluorine-containing inorganic acid and sodium nitrite in an organic solvent to generate diazonium salt, and then heating and decomposing to obtain 2-fluoro-3, 4-dichloronitrobenzene; and (4) reducing the 2-fluoro-3, 4-dichloronitrobenzene, so as to obtain the 3, 4-dichloro-2-fluoroaniline. According to the method, 1, 2, 3-trichlorobenzene serves as a raw material, and 3, 4-dichloro-2-fluoroaniline is obtained through the processes of nitration, ammonolysis, diazotization, decomposition, reduction and the like; the method provides a synthetic route of 3, 4-dichloro-2-fluoroaniline, and has the characteristics of simple process, easily controlled process, high product yield, high purity, low production cost and the like.

Preparation method of 2,3-dichloro-6-nitroaniline

The invention relates to the technical field of pesticides, in particular to a preparation method of 2,3-dichloro-6-nitroaniline. The method comprises the following steps: preparing 2,3,4-trichloronitrobenzene as a raw material, water as a solvent and a sulfur-containing compound as a catalyst, carrying out a reaction with ammonia water in a high-pressure kettle to obtain the 2,3-dichloro-6-nitroaniline. The preparation method of 2, 3-dichloro-6-nitroaniline provided by the invention is high in yield, good in reaction selectivity, high in safety, environment-friendly, low in production cost and suitable for industrial production; by adding a small amount of the sulfur-containing catalyst, a good catalytic effect can be achieved, high yield of 99% or above and selectivity of 99% or above can be finally obtained, the reaction time is greatly shortened, and the production energy consumption is reduced.

2, 3-dichloro-6-nitroaniline and preparation method thereof

Belonging to the field of organic synthesis, the invention relates to 2, 3-dichloro-6-nitroaniline and a preparation method thereof. According to the invention, 2, 3-dichloro-6-nitroaniline is prepared by a two-step method. The method includes: firstly taking 1, 2, 3-trichlorobenzene as the raw material to carry out nitration reaction with nitric acid in a sulfuric acid system to prepare 2, 3, 4-trichloronitrobenzene; and then carrying out ammonolysis reaction on the 2, 3, 4-trichloronitrobenzene and ammonia water in an organic solvent at 120-150DEG C so as to obtain DCONA. The preparation method has the advantages of simple operation, mild reaction conditions, high yield and purity, and green and environment protection, and the sulfuric acid, organic solvent and ammonia water used in the preparation process can all be effectively recovered.

Small molecule inhibition of cGAS reduces interferon expression in primary macrophages from autoimmune mice

Cyclic GMP-AMP synthase is essential for innate immunity against infection and cellular damage, serving as a sensor of DNA from pathogens or mislocalized self-DNA. Upon binding double-stranded DNA, cyclic GMP-AMP synthase synthesizes a cyclic dinucleotide that initiates an inflammatory cellular response. Mouse studies that recapitulate causative mutations in the autoimmune disease Aicardi-Goutières syndrome demonstrate that ablating the cyclic GMP-AMP synthase gene abolishes the deleterious phenotype. Here, we report the discovery of a class of cyclic GMP-AMP synthase inhibitors identified by a high-throughput screen. These compounds possess defined structure-activity relationships and we present crystal structures of cyclic GMP-AMP synthase, double-stranded DNA, and inhibitors within the enzymatic active site. We find that a chemically improved member, RU.521, is active and selective in cellular assays of cyclic GMP-AMP synthase-mediated signaling and reduces constitutive expression of interferon in macrophages from a mouse model of Aicardi-Goutières syndrome. RU.521 will be useful toward understanding the biological roles of cyclic GMP-AMP synthase and can serve as a molecular scaffold for development of future autoimmune therapies.

CARBONYL LINKED BICYCLIC HETEROARYL N-BENZIMIDAZOLES AND ANALOGS AS ANTIBIOTIC TOLERANCE INHIBITORS

The disclosure provides compounds and pharmaceutical compositions of includes carbonyl linked bicyclic heteroaryl N-benzimidazole compounds useful for treating chronic and acute bacterial infections. Certain of the compounds are compounds of general Formula (I) or a pharmaceutically acceptable salt or prodrug thereof. Certain compounds of this disclosure are MvfR inhibitors. MvfR inhibitors reduce the formation of antibiotic tolerant bacterial strains and are useful for treating Gram-negative bacterial infections and reducing the virulence of Pseudomonas aeruginosa. Methods of treating bacterial infections in a subject, including Pseudomonas aeruginosa infections, are also provided by the disclosure.

Design, synthesis, and preliminary in vitro and in silico antiviral activity of [4,7]phenantrolines and 1-oxo-1,4-dihydro-[4,7]phenantrolines against single-stranded positive-sense RNA genome viruses

Following the antiviral screening of a wide series of new angular and linear N-tricyclic systems both in silico and in vitro, the [4,7]phenantroline nucleus emerged as a new ring system endowed with activity against viruses containing single-stranded, positive-sense RNA genomes (ssRNA+). Here, we report our new pathway to the synthesis of this nucleus and of several related derivatives, as well as the results of both cell-based antiviral assays and molecular dynamics simulations. In the antiviral screening, several compounds (9 and 16-20) showed to be fairly active against BVDV, CVB-2, and Polio 1 (EC50, 6-25 μM). According to molecular dynamics simulations, compounds (15) and (17) emerged for its potency against the HCV NS5B, with a calculated IC50 of 11-12 μM.

Synthesis of two novel tricyclic rings: Triazolo[4,5-g]- quinolines and pyrido[2,3-g]quinoxalines derived from 6,7-diaminoquinolines

A general simple route for the synthesis of triazolo[4,5-g]quinolines and pyrido[2,3-g]quinoxalines is described. The heterocycles obtained were fully characterised by their spectroscopical properties. A revision of the nitration of the 2,3-dichloroacetanilide is also discussed, since it afforded the request nitro derivative to build up the key intermediate 6,7- diaminoquinolines.

A convenient copper-catalyzed direct animation of nitroarenes with 9-alkylhydroxylamines

O-Alkylhydroxylamines, particularly O-methylhydroxylamine, aminate nitroarenes in the presence of a strong base and a copper catalyst to give aminonitroarenes in good yields, ortho- or para-Animation with respect to the nitro group takes place, and in some cases the ortho-aminated product is preferentially obtained. With 3-substituted nitrobenzenes where the substituent has a lone pair of electrons, preferential amination occurs at the 2-position to give the sterically most congested 3c-f, 14 and 22g.

Structure-activity relationships among 2-substituted 5,6-dichloro-, 4,6- dichloro-, and 4,5-dichloro-1-[(2-hydroxyethoxy)methyl]- and -1-[(1,3- dihydroxy-2-propoxy)methyl]benzimidazoles

The sodium salt of 2,5,6-trichlorobenzimidazole (8a) was condensed with [2-(benzyloxy)ethoxy]methyl chloride (9) and [1,3-bis(benzyloxy)-2- propoxy]methyl chloride (18) to provide the corresponding protected acyclic nucleosides 10a and 19a, which on debenzylation afforded 2,5,6-trichloro-1- [(2-hydroxyethoxy)methyl]benzimidazole (11a) and 2,5,6-trichloro-1-[(1,3- dihydroxy-2-propoxy)methyl]benzimidazole (20a), respectively. A similar condensation of 2,4,6-trichlorobenzimidazole (2a) and 2,4,5- trichlorobenzimidazole (7a) followed by debenzylation yielded 11b, 20b, 11c, and 20c, respectively. A nucleophilic displacement of the 2-chloro group of 11a-c and 20a-c with liquid ammonia, methylamine, dimethylamine, and thiourea furnished several interesting 2-substituted compounds in good yields, e.g., 12-14(a-e), 2123(a-e), 15-17, and 24-26. Alkylation of the 2-thio analogs 15- 17 and 24-26 with benzyl chloride furnished the 2-alkylthio acyclic nucleosides 12d-14d and 21d-23d. Desulfurization of 15 and 24 with Raney Ni furnished 5,6-dichloro-1-[(2-hydroxyethoxy)methyl]benzimidazole (12e) and 5,6-dichloro-1-[(1,3-dihydroxy-2-propoxy)methyl]benzimidazole (21e), respectively (acyclic analog of 5,6-dichloro-1-β-D- ribofuranosylbenzimidazole). Similarly the dihalo compounds 13e, 14e, and 23e were prepared in moderate yields from the 2-thio analogs 16, 17, and 26. Treatment of 2-bromo-5,6-dichlorobenzimidazole (8b) with 27 and 30 gave the protected acyclic compounds 28a and 31a, which on deacetylation with sodium carbonate and potassium cyanide yielded 2-bromo-5,6-dichloro-1-[(2- hydroxyethoxy)methyl]benzimidazole (29a) and 2-bromo-5,6-dichloro-1-[(1,3- dihydroxy-2-propoxy)methyl]benzimidazole (32a), respectively, in moderate yields. The 2-bromo-4,6-dichlorobenzimidazole and 2-bromo-4,5- dichlorbenzimidazole analogs 29b,c and 32b,c were prepared in a similar manner. Compounds were tested for activity against human cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1) and for cytotoxicity. In marked contrast to the ribosylbenzimidazoles, none of the acyclic analogs were specific and potent inhibitors of HCMV. Only the 2-thiobenzyl analogs 12d, 13d, 14d, and 23d and the 2-Br analogs 32a,b were active, but activity was not well separated from cytotoxicity. The lack of specific and potent antiviral activity strongly suggests that these acyclic nucleoside analogs are not phosphorylated by HCMV or HSV-1 gene products and that the ribosylbenzimidazoles do not require phosphorylation for antiviral activity.

The Influence of Chlorine and Sulphonate Substituents on the Visible Absorption Maxima of Some Azo Dyes

A total of 110 arylazo dyes have been prepared, based on five benzenoid and heterocyclic coupling components, and containing combinations of chlorine and sulphonate (sulpho) substituents in the diazo components.Their visible absorption maxima have been analysed in order to determine the degree to which chloro and sulfo substituent influences are constant and transferable, both within a series, and between series.Additivity is found to pertain, if allowances are made for steric effects.A 2-sulpho group alone can induce nonplanarity, depending on the nature of the coupling component.The 2-sulpho-3-chloro combination is particularly responsible for hypsochromic shifts unexpected on the basis of strict additivity.Computer-aided molecular modelling studies have clarified the steric interactions present.Di-ortho-substitution also induces nonplanarity and hypsochromic effects.There is some evidence for non-equivalence of a substituent in the two distinct meta-orientations, although MO calculations do not reproduce this behaviour.