34893-92-0

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Dichlorophenyl isocyanate is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a valuable building block for the development of new drugs, contributing to the advancement of medicine.
Used in Agricultural Industry:
In the agricultural sector, 3,5-Dichlorophenyl isocyanate is utilized in the production of iprodione, a widely used fungicide. Iprodione is effective in controlling a range of fungal diseases in crops, making it an essential component in ensuring food security and crop protection.
Used in Proteomic Research:
3,5-Dichlorophenyl isocyanate also finds application in proteomic research, where it is employed as a chemical probe to study protein structure, function, and interactions. Its reactivity with proteins allows researchers to gain insights into the molecular mechanisms underlying various biological processes, ultimately contributing to a better understanding of life sciences.

Potential Exposure

Those materials used as chemical intermediates

Shipping

UN2250 Dichlorophenyl isocyanates, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Incompatibilities

May form explosive mixture with air. Isocyanates are highly flammable and reactive with many compounds, even with themselves. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Reaction with moist air, water or alcohols may form amines and insoluble polyureas and react exothermically, releasing toxic, corrosive or flammable gases, including carbon dioxide; and, at the same time, may generate a violent release of heat increasing theconcentration of fumes in the air. Incompatible with amines, aldehydes, alkali metals, ammonia, carboxylic acids, caprolactum, alkaline materials, glycols, ketones, mercaptans, hydrides, organotin catalysts, phenols, strong acids, strong bases, strong reducing agents such as hydrides, urethanes, and ureas. Elevated temperatures or contact with acids, bases, tertiary amines, and acylchlorides may cause explosive polymerization. Contact with metals may evolve flammable hydrogen gas. Attacks some plastics, rubber, and coatings.

Waste Disposal

Combustion in an incinerator equipped with afterburner and fume scrubber

InChI:InChI=1/C7H3Cl2NO/c8-5-1-6(9)3-7(2-5)10-4-11/h1-3H

Upstream product

• 152723-53-0 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 626-43-7 3,5-Dichloroaniline 
• 32809-16-8 procymidon 
• 75-44-5 phosgene 
• 879281-85-3 benzoyl azide 
• 51-36-5 3,5-dichlorobenzoic acid 
• 13330-18-2 3,5-dichloroaniline hydrochloride 

Downstream Products

• 104115-90-4 N-(3,5-dichloro-phenyl)-N'-(5-nitro-[2]pyridyl)-urea 
• 40397-45-3 2-Hydroxy-6-oxo-cyclohex-1-enecarboxylic acid (3,5-dichloro-phenyl)-amide 
• 40397-47-5 2-Hydroxy-4,4-dimethyl-6-oxo-cyclohex-1-enecarboxylic acid (3,5-dichloro-phenyl)-amide 
• 86353-75-5 (3,5-Dichloro-phenyl)-carbamic acid 1-methyl-4,5-dihydro-1H-imidazol-2-ylmethyl ester 
• 86781-32-0 1,1-di-(n-butyl)-3-(3,5-dichlorophenyl)urea 
• 213208-73-2 (5R)-5-(4-bromobenzyl)-3-(3,5-dichlorophenyl)-5-methyl-1H-imidazole-2,4(3H,5H)-dione 
• 403607-17-0 N-allyl-N'-methyl-3α-N-(3,5-dimethylbenzoyl)amino-12α-(3,5-dichlorophenyl)carbamoyloxy-5β-cholan-24-amide 
• 403607-22-7 N-allyl-N'-methyl-3α-(3,5-dichlorophenyl)carbamoyloxy-12α-N-(3,5-dimethylbenzoyl)amino-5β-cholan-24-amide 
• 403607-16-9 N-allyl-N'-methyl-3α-N-(3,5-dichlorobenzoyl)amino-12α-(3,5-dichlorophenyl)carbamoyloxy-5β-cholan-24-amide 
• 403607-20-5 N-allyl-N'-methyl-3α-(3,5-dichlorophenyl)carbamoyloxy-12α-(3,5-dichlorobenzoyl)amino-5β-cholan-24-amide 
• 466671-56-7 1-(3,5-dichloro-phenyl)-3-{4-[(5-dimethylaminomethyl-furan-2-yl)-hydroxy-methyl]-benzyl}-urea 
• 466671-45-4 1-(3,5-dichloro-phenyl)-3-{4-[1-(toluene-4-sulfonyl)-1H-pyrrole-3-carbonyl]-benzyl}-urea 
• 224585-58-4 1-(3,5-dichloro-phenyl)-3-[4-(1-trityl-1H-imidazol-4-ylmethyl)-benzyl]-urea 
• 466671-51-2 1-(3,5-dichloro-phenyl)-3-{4-[hydroxy-(1-trityl-1H-pyrazol-4-yl)-methyl]-benzyl}-urea 

Relevant academic research and scientific papers

Ultraviolet degradation of procymidone - Structural characterization by gas chromatography coupled with mass spectrometry and potential toxicity of photoproducts using in silico tests

RATIONALE Procymidone is a dicarboximide fungicide mainly used for vineyard protection but also for different crops. The structural elucidation of by-products arising from the UV-visible photodegradation of procymidone has been investigated by gas chromatography coupled with mass spectrometry. The potential toxicities of photoproducts were estimated by in silico tests. METHODS Aqueous solutions of procymidone were irradiated for up to 90 min in a self-made reactor equipped with a mercury lamp. Analyses were carried out on a gas chromatograph coupled with an ion trap mass spectrometer operated in electron ionization and methanol positive chemical ionization. Multistage collision-induced dissociation (CID) experiments were performed to establish dissociation pathways of ions. Toxicities of byproducts were estimated using the QSAR T.E.S.T. program. RESULTS Sixteen photoproducts were investigated. Chemical structures were proposed mainly based on the interpretation of multistage CID experiments, but also on their relative retention times and kinetics data. These structures enabled photodegradation pathways to be suggested. Only three photoproducts remain present after 90 min of irradiation. Among them, 3,5-dichloroaniline presents a predicted rat LD50 toxicity about ten times greater than that of procymidone. CONCLUSIONS 3,5-Dichloroaniline is the only photoproduct reported in previous articles. Eight by-products among the sixteen characterized might be as toxic, if not more, than procymidone itself considering the QSAR-predicted rat LD50. Copyright 2013 John Wiley & Sons, Ltd. Copyright

Novel 5-fluorouracil sensitizers for colorectal cancer therapy: Design and synthesis of S1P receptor 2 (S1PR2) antagonists

Sphingosine-1-phosphate receptor 2 (S1PR2) has been identified as a brand-new GPCR target for designing antagonists to reverse 5-FU resistance. We herein report the structural optimization and structure-activity relationship of JTE-013 derivatives as S1PR2 antagonists. Compound 9d was the most potent S1PR2 antagonist (KD = 34.8 nM) among developed compounds. Here, compound 9d could significantly inhibit the expression of dihydropyrimidine dehydrogenase (DPD) to reverse 5-FU-resistance in HCT116DPD and SW620/5-FU cells. Further mechanism studies demonstrated that compound 9d not only inhibited S1PR2 but also affected the transcription of S1PR2. In addition, compound 9d also showed acceptable selectivity to normal cells (NCM460). Importantly, compound 9d with suitable pharmacokinetic properties could significantly reverse 5-FU-resistance in the HCT116DPD and SW620/5-FU xenograft models without obvious toxicity, in which the inhibition rates of 5-FU were increased from 23.97% to 65.29% and 27.23% to 60.81%, respectively. Further immunohistochemistry and western blotting analysis also demonstrated that compound 9d significantly decreases the expression of DPD in tumor and liver tissues. These results indicated that compound 9d is a promising lead compound to reverse 5-FU-resistance for colorectal cancer therapy.

Staphylococcus aureus rnpa inhibitors: Computational-guided design, synthesis and initial biological evaluation

Antibiotic resistance is spreading worldwide and it has become one of the most important issues in modern medicine. In this context, the bacterial RNA degradation and processing machinery are essential processes for bacterial viability that may be exploited for antimicrobial therapy. In Staphylococcus aureus, RnpA has been hypothesized to be one of the main players in these mech-anisms. S. aureus RnpA is able to modulate mRNA degradation and complex with a ribozyme (rnpB), facilitating ptRNA maturation. Corresponding small molecule screening campaigns have recently identified a few classes of RnpA inhibitors, and their structure activity relationship (SAR) has only been partially explored. Accordingly, in the present work, using computational modeling of S. aureus RnpA we identified putative crucial interactions of known RnpA inhibitors, and we used this information to design, synthesize, and biologically assess new potential RnpA inhibitors. The present results may be beneficial for the overall knowledge about RnpA inhibitors belonging to both RNPA2000-like thiosemicarbazides and JC-like piperidine carboxamides molecular classes. We evaluated the importance of the different key moieties, such as the dichlorophenyl and the piperidine of JC2, and the semithiocarbazide, the furan, and the i-propylphenyl ring of RNPA2000. Our efforts could provide a foundation for further computational-guided investigations.

SULPHONYL UREA DERIVATIVES AS NLRP3 INFLAMMASOME MODULATORS

The present disclosure relates to compounds of Formula (I): (I) and to their pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for inhibiting the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as inflammatory, autoinflammatory and autoimmune diseases and cancers.

Method for preparing isocyanate by using amine and carbonyl fluoride

The invention discloses an efficient synthesis method for preparing corresponding isocyanate by enabling carbonyl fluoride to directly react with amine. The efficient synthesis method mainly comprises the following two steps: carrying out acylation reaction on the amine and the carbonyl fluoride according to a preferable proportion in an anhydrous inertial organic solvent under a sealed environment and a proper reaction condition, thus generating an intermediate-carbamyl fluoride; (2) carrying out dehydrofluorination on the intermediate-carbamyl fluoride under normal pressure and the proper reaction condition, thus obtaining the target isocyanate. During a reaction process, addition of a catalyst is not needed, the reaction conditions are mild, excessive carbonyl fluoride and a used solvent during the reaction process can be efficiently recycled and reused, and a by-product HF can be commercially sold after being collected and refined.

Preparation of 3 - (3,5-dichlorophenyl) - 2,4-imidazolidinedione method

The invention discloses a method for preparing 3-(3, 5-dichlorophenyl)-2, 4-imidazolidinedione with a structure as shown in a formula (I). The method comprises the following steps: (1) contacting one or a plurality of compounds shown by a formula (III) with compounds shown by a formula (II) under condensation reaction conditions in the presence of a condensation reaction catalyst and an organic solvent to obtain a mixture containing compounds shown by a formula (IV); and (2) directly contacting the mixture containing compounds shown by the formula (IV) with a ring closing reaction catalyst or separating out the compounds shown by the formula (IV) and contacting the compounds with the ring closing reaction catalyst under ring closing reaction conditions. The reaction yield of the method is high, and the intermediate does not need to be separated or purified, so that the steps are simple.

Method for recycling phosgene in tail gas produced through thermo-optical reaction for synthesis of 3,5-dichlorophenyl isocyanate

The invention discloses a method for recycling phosgene in tail gas produced through a thermo-optical reaction for synthesis of 3,5-dichlorophenyl isocyanate. The method comprises steps as follows: a phosgene-toluene solution in a tail gas cooling pan is fed into a cold-light kettle, a 3,5-dichloroaniline toluene liquid in a dropping addition tank is dropwise added to the cold-light kettle, and phosgene I is introduced from the bottom of the cold-light kettle; a mixed solution is transferred into a thermo-optical kettle, and phosgene II is introduced from the bottom of the thermo-optical kettle until the toluene solution is transparent; gas produced in a reaction process enters a thermo-optical condenser, non-condensing gas is introduced into a thermo-optical tail gas buffer kettle and is heated to 80 DEG C, and the heated gas is introduced into the tail gas cooling pan; a condensed liquid in the thermo-optical condenser and a liquid in the thermo-optical tail gas buffer kettle are subjected to acid distribution treatment, a product is introduced into the thermo-optical kettle through a pipe, and reflux is formed; N2 is introduced from the bottom of the thermo-optical kettle in a reflux process for light repelling; a material is flirted by a filter device, then is introduced into an intermediate tank and is introduced into a next procedure through a pump P1.

N-substituted 2-isonicotinoylhydrazinecarboxamides-new antimycobacterial active molecules

This report presents a new modification of the isoniazid (INH) structure linked with different anilines via a carbonyl group obtained by two synthetic procedures and with N-substituted 5-(pyridine-4-yl)-1,3,4-oxadiazole-2-amines prepared by their cyclisation. All synthesised derivatives were characterised by IR, NMR, MS and elemental analyses and were evaluated in vitro for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv, Mycobacterium avium 330/88, Mycobacterium kansasii 235/80 and one clinical isolated strain of M. kansasii 6509/96. 2-Isonicotinoyl-N-(4- octylphenyl)hydrazinecarboxamide displayed an in vitro efficacy comparable to that of INH for M. tuberculosis with minimum inhibitory concentrations (MICs) of 1-2 μM. Among the halogenated derivatives, the best anti-tuberculosis activity was found for 2-isonicotinoyl-N-(2,4,6-trichlorophenyl) hydrazinecarboxamide (MIC = 4 μM). In silico modelling on the enoyl-acyl carrier protein reductase InhA confirmed that longer alkyl substituents are advantageous for the interactions and affinity to InhA. Most of the hydrazinecarboxamides, especially those derived from 4-alkylanilines, exhibited significant activity against INH-resistant nontuberculous mycobacteria. gfjh+l;kfldf.

Synthesis and in vitro antitumor activity of novel diaryl urea derivatives

A series of novel diaryl ureas containing 4-[(2-amino-6-trifluromethyl) pyrimidine-4-yl]piperazine-1-yl group were synthesized and evaluated for their cytotoxic activities in a panel of human cancer cell lines. Compared with the reference drug Sorafenib, some compounds showed more potent and a broader spectrum of anti-cancer activities. Among them, compound 2p demonstrated significant inhibitory activities against MDA-MB-231, HT-29 and MCF-7 cell lines with IC50 values of 0.016, 0.63, 0.001 μmol/L, respectively.

Specific inhibitors of puromycin-sensitive aminopeptidase with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton

Specific puromycin-sensitive aminopeptidase (PSA) inhibitors with a 3-(halogenated phenyl)-2,4(1H,3H)-quinazolinedione skeleton were prepared and their structure-activity relationships were investigated. The nature (F, Cl or Br), number and position(s) of the halogen atom(s) introduced into the 3-phenyl group were concluded to be critical determinants of the inhibitory activity.