615-47-4

Basic information

• Product Name: 1,2,4-Benzenetriamine dihydrochloride
• Synonyms: benzene-1,2,4-triyltriamine dihydrochloride;1,2,4-Benzenetriamine 2HCL;1,2,4-TRIAMINOBENZENE 2HCL;1,2,4-Benzenetriamine dihydrochloride, pract., 99%;1,2,4-BENZENETRIAMINE DIHYDROCHLORIDE PRACT., 99% (TITR.);1,2,4-Benzenetriamine dihydrochloride,99%,pract.;Benzene-1,2,4-triaMine 2HCl;benzene-1,2,4-triaMine dihydrochloride
• CAS NO: 615-47-4
• Molecular Formula: C6H11Cl2N3
• Molecular Weight: 196.08
• EINECS: 210-428-1
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Benzene derivates;Furans ,Coumarins
• Mol File: 615-47-4.mol

Chemical Properties

• Melting Point: 290°C
• Boiling Point: 342.5°C at 760 mmHg
• Flash Point: 191.2°C
• Appearance: /
• Vapor Pressure: 7.51E-05mmHg at 25°C
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: slightly soluble
• Water Solubility: slightly soluble
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• CAS DataBase Reference: 1,2,4-Benzenetriamine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Benzenetriamine dihydrochloride(615-47-4)
• EPA Substance Registry System: 1,2,4-Benzenetriamine dihydrochloride(615-47-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37
• RTECS: DC1953000
• TSCA: Yes
• Hazardous Substances Data: 615-47-4(Hazardous Substances Data)

Usage

Uses

Used in Fluorescent Carbon Dots Production:
1,2,4-Benzenetriamine dihydrochloride is used as a reagent for the creation of multicolor fluorescent carbon dots. These dots can be detected using white-light-emitting diodes and water, making them potentially useful in various applications where fluorescence detection is required.
Used in Fluorescent Carbon Nanomaterials:
In the field of aconitic acid-based fluorescent carbon nanomaterials, 1,2,4-Benzenetriamine dihydrochloride serves as a co-doping reagent. Its use allows for the preparation of materials with a high quantum yield and the ability to control the emission wavelength. This makes it a valuable component in the development of advanced nanomaterials with specific optical properties for various applications, such as sensing, imaging, or lighting.

Synthesis

(1) Using m-dichlorobenzene as raw material, dropwise addition at low temperature and high temperature nitration in a mixed acid system of concentrated sulfuric acid and fuming nitric acid to obtain 1,3-dichloro-4,6-dinitrobenzene; (2) 1 ,3-Dichloro-4,6-dinitrobenzene is placed in a high-pressure reactor in the presence of ammonia water, and the temperature is raised to 145～150 ℃ for ammonolysis reaction to obtain 4,6-dinitro-1,3-benzenediol Amine; (3) Place 4,6-dinitro-1,3-phenylenediamine, oxygen-free distilled water and palladium-carbon catalyst in a hydrogenation autoclave, and catalyze it under a hydrogen atmosphere of 1-1.5MPa and 85°C After the hydrogenation reaction, the catalyst was removed by hot filtration under nitrogen protection to obtain a 1,2,4-triaminobenzene hydrochloric acid solution;(4) take the 1,2,4,5-tetraaminobenzene obtained in step (3) The solution was added with concentrated hydrochloric acid, cooled to room temperature, filtered under nitrogen protection, and the filter cake was dried in a vacuum desiccator at 40°C to obtain 1,2,4-triaminobenzene hydrochloric acid. The molar ratio of m-dichlorobenzene to fuming nitric acid described in the step (1) is 2.2:1, the mass ratio of concentrated sulfuric acid to fuming nitric acid is 3:8～10, and the dropping temperature is -5～0°C, The nitration temperature is 100-104°C. The reaction time of the ammonolysis described in step (2) is 3.5～4h, and the molar ratio of 1,3-dichloro-4,6-dinitrobenzene to ammonia water is 1:(10～14). The oxygen-free distilled water described in step (3) is distilled water purified by nitrogen, and the reaction time of catalytic hydrogenation is 3-4h; 4,6-dinitro-1,3-phenylenediamine, palladium-carbon catalyst and oxygen-free The mass ratio of the three distilled water is 1:0.05:10. The volume ratio of the 1,2,4-triaminobenzene hydrochloric acid solution described in step (4) to concentrated hydrochloric acid is 1:0.2-0.3.

InChI:InChI=1/C6H9N3.2ClH/c7-4-1-2-5(8)6(9)3-4;;/h1-3H,7-9H2;2*1H

Upstream product

• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 97-02-9 2,4-Dinitroanilin 
• 58048-37-6 2-(2,4-dichloro-phenoxy)-propionyl chloride 
• 120-36-5 2-(2,4-dichlorophenoxy)propionic acid 
• 535-11-5 Ethyl 2-bromopropionate 
• 120-83-2 2,4-dichlorophenol 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 42412-84-0 ethyl 2-phenoxypropionate 

Downstream Products

• 108281-61-4 2-benzyl-1H-benzo[d]imidazol-5-amine 
• 7576-88-7 2,3-dimethyl-6-quinoxalinamine 
• 4236-41-3 3-methyl-6-aminoquinoxaline 
• 28689-19-2 2,2'-(1,4-phenylene)bis(1H-benzo[d]imidazol-6-amine) 
• 7621-86-5 6-amino-2-(4'-aminophenyl)-benzimidazole 
• 70500-02-6 2-(3-chloro-4-aminophenyl)-6⁽⁵⁾-aminobenzimidazole 
• 6298-37-9 6-aminoquinoxaline 
• 1571-93-3 2-methyl-1(3)H-benzimidazol-5-ylamine; dihydrochloride 
• 7621-86-5 2-(4-aminophenyl)-5-amino-benzimidazole 
• 87345-63-9 N,N'-Bis<2-(4-nitrophenyl)benzimidazol-5-yl>terephthaloyl diamide 
• 87345-62-8 1,5-Bis(p-nitrobenzamido)-2-(p-nitrophenyl)benzimidazole 

Relevant articles and documents

Preparation method of chlorophenoxycarboxylic ester

The invention provides a preparation method of chlorophenoxycarboxylic ester, wherein the preparation method includes the following steps: carrying out 2-site and/or 4-site selective chlorination reaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, and the catalyst B is C5-22 thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof. The method effectively improves the chlorination selectivity and avoids loss of effective ingredients by redesigning of the process route and fine screening of the catalysts and the chlorinating agent. The content of the obtained chlorophenoxycarboxylic ester can reach 98.5% or more and the yield can reach 99% or more.

Preparation method of chlorophenoxycarboxamide salt

The invention provides a preparation method of chlorophenoxycarboxamide salt, wherein the preparation method includes the following steps: S1) carrying out 2-site and/or 4-site selective chlorinationreaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, and the catalyst B is C5-22 thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof; and S2) carrying out ammonolysis reaction of chlorophenoxycarboxylic ester and amine to obtain chlorophenoxycarboxamide salt. By redesigning of the process route and fine screening of the catalysts and the chlorinating agent, the method reduces energy consumption, improves chlorination selectivity and avoids loss of effective components. The yield of the obtained chlorophenoxycarboxamide salt can reach 99% or more. At the same time, the production of high-salt wastewater is completely eradicated, thedust hazard caused by drying and use of chlorophenoxycarboxylic acid is avoided, energy is saved and equipment investment is reduced.

Preparation method of chlorophenoxycarboxylic ester

The invention provides a preparation method of chlorophenoxycarboxylic ester, wherein the preparation method includes the following steps: S1) carrying out 2-site and/or 4-site selective chlorinationreaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, the catalyst B is C5-22 thiazoles, isothiazoles and thiophenes or halogenated derivatives thereof, and the phenoxycarboxylic ester has any structure represented by the formulas I-IV; and S2) carrying out transesterification reaction of chlorophenoxycarboxylic ester and alcohol under the action of a catalyst to obtain long-chain chlorophenoxycarboxylic ester, wherein the alcohol has the molecular formula ofR2OH, and R2 is C4-20 alkyl or cycloalkyl. The method improves the yield and purity of chlorophenoxycarboxylic ester by redesigning of the process route and fine screening of the catalysts and the chlorinating agent. The content of the obtained chlorophenoxycarboxylic ester can reach 98.5% or more and the yield can reach 98.5% or more.

Preparation method of chlorophenoxycarboxylic ester

The invention provides a preparation method of chlorophenoxycarboxylic ester, wherein the preparation method includes the following steps: carrying out 2-site and/or 4-site selective chlorination reaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, and the catalyst B has the following structural formula of R1'-S-R2'. The method effectively improves the chlorination selectivity and avoids loss of effective ingredients by redesigning of the process route and fine screening of the catalysts and the chlorinating agent. The content of the obtained chlorophenoxycarboxylic ester can reach 98.5% or more and the yield can reach 99% or more.

Preparation method of chlorophenoxycarboxylic ester

The invention provides a preparation method of chlorophenoxycarboxylic ester, wherein the preparation method includes the following steps: S1) carrying out 2-site and/or 4-site selective chlorinationreaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, the catalyst B has the following structural formula of R1'-S-R2', and the phenoxycarboxylic ester has any structure represented by the formulas I-IV; and S2) carrying out transesterification reaction of chlorophenoxycarboxylic ester and alcohol under the action of a catalyst to obtain long-chain chlorophenoxycarboxylic ester, wherein the alcohol has the molecular formula of R2OH, and R2 is C4-20 alkyl or cycloalkyl. The method improves the yield and purity of chlorophenoxycarboxylic ester by redesigning of the process route and fine screening of the catalysts and the chlorinating agent. The content ofthe obtained chlorophenoxycarboxylic ester can reach 98.5% or more and the yield can reach 98.5% or more.

A [...] ester preparation method (by machine translation)

The invention provides a method for preparing [...] ester, including: the phenoxy carboxylic acid ester compounds, supported Lewis acid catalyst, sulfur-containing polymer mixed with the chlorinating agent, the selective chlorination reaction, to obtain [...] ester. Compared with the prior art, this invention uses benzene oxygen suo acid ester compound as a raw material obtained by the selective chlorination of [...] ester, simple preparation method, to avoid having the bad smell of the Fe0 production and use, thereby fundamentally preventing the substance to the dioxin generation; at the same time supported Lewis acid and sulfur-containing polymer common as catalyst, through the two cooperative positioning function, the selectivity of the dichloride to improve, and the two can through the filter recovery and re-use, the use of the recycling of the catalyst; furthermore the invention avoids the losses of the active ingredient, the extraction rate of the product, reduces energy consumption, prevent high COD, the generation of high salt waste water, three waste output has been largely reduced. (by machine translation)

Preparation method of chlorophenoxycarboxamide salt

The invention provides a preparation method of chlorophenoxycarboxamide salt, wherein the preparation method includes the following steps: S1) carrying out 2-site and/or 4-site selective chlorinationreaction of phenoxycarboxylic ester with a chlorinating agent under the action of a catalyst A and a catalyst B to obtain chlorophenoxycarboxylic ester, wherein the catalyst A is Lewis acid, and the catalyst B has the following structural formula of R1'-S-R2'; and S2) carrying out ammonolysis reaction of chlorophenoxycarboxylic ester and amine to obtain chlorophenoxycarboxamide salt. By redesigning of the process route and fine screening of the catalysts and the chlorinating agent, the method reduces energy consumption, improves chlorination selectivity and avoids loss of effective components.The yield of the obtained chlorophenoxycarboxamide salt can reach 98.5% or more. At the same time, the production of high-salt wastewater is completely eradicated, the dust hazard caused by drying and use of chlorophenoxycarboxylic acid is avoided, energy is saved and equipment investment is reduced.

PROCESS FOR THE PREPARATION OF AROMATIC AZOLE COMPOUNDS

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Optimization of benzoxazole-based inhibitors of Cryptosporidium parvum inosine 5′-monophosphate dehydrogenase

Cryptosporidium parvum is an enteric protozoan parasite that has emerged as a major cause of diarrhea, malnutrition, and gastroenteritis and poses a potential bioterrorism threat. C. parvum synthesizes guanine nucleotides from host adenosine in a streamlined pathway that relies on inosine 5′-monophosphate dehydrogenase (IMPDH). We have previously identified several parasite-selective C. parvum IMPDH (CpIMPDH) inhibitors by high-throughput screening. In this paper, we report the structure-activity relationship (SAR) for a series of benzoxazole derivatives with many compounds demonstrating CpIMPDH IC50 values in the nanomolar range and >500-fold selectivity over human IMPDH (hIMPDH). Unlike previously reported CpIMPDH inhibitors, these compounds are competitive inhibitors versus NAD +. The SAR study reveals that pyridine and other small heteroaromatic substituents are required at the 2-position of the benzoxazole for potent inhibitory activity. In addition, several other SAR conclusions are highlighted with regard to the benzoxazole and the amide portion of the inhibitor, including preferred stereochemistry. An X-ray crystal structure of a representative E·IMP·inhibitor complex is also presented. Overall, the secondary amine derivative 15a demonstrated excellent CpIMPDH inhibitory activity (IC 50 = 0.5 ± 0.1 nM) and moderate stability (t1/2 = 44 min) in mouse liver microsomes. Compound 73, the racemic version of 15a, also displayed superb antiparasitic activity in a Toxoplasma gondii strain that relies on CpIMPDH (EC50 = 20 ± 20 nM), and selectivity versus a wild-type T. gondii strain (200-fold). No toxicity was observed (LD 50 > 50 μM) against a panel of four mammalian cells lines.