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541-41-3Relevant articles and documents
Photocatalysis of chloroform decomposition by the hexachlororuthenate(IV) ion
Chan, Alissa M.,Pena, Laura A.,Segura, Rosa E.,Auroprem, Ramya,Harvey, Brent M.,Brooke, Caroline M.,Hoggard, Patrick E.
, p. 274 - 279 (2013)
Dissolved hexachlororuthenate(IV) effectively catalyzes the photodecomposition of chloroform to hydrogen chloride and phosgene under near-UV (λ > 345 nm) irradiation, whereby RuCl62- is not itself photocatalytically active, but is photochemically transformed into a species that is active, possibly RuCl5(CHCl3)-. Conversion to a photoactive species during irradiation is consistent with the acceleration of the decomposition rate during the early stages and with the apparent inverse dependence of the decomposition rate on the initial concentration of RuCl62-. The displacement of Cl - by CHCl3 in the coordination sphere to create the photoactive species is consistent with the retardation of photodecomposition by both Cl- and H2O. The much smaller photodecomposition rate in CDCl3 suggests that C-H bond dissociation occurs during the primary photochemical event, which is also consistent with the presence of a CHCl3 molecule in the first coordination sphere. In the presence of RuCl62-, chloroform decomposes under near-UV irradiation to phosgene and hydrogen chloride. The photoactive species is suggested to be RuCl5(CHCl3) -.
New production process of hexazinone key raw material WT-02
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Paragraph 0026-0028, (2021/08/19)
The invention belongs to the field of fine chemical engineering, and particularly relates to a new production process of a hexazinone key raw material WT-02, which comprises the procedures of high-pressure reaction, Oppenauer oxidation, acyl chloride amination and condensation. The method has the advantages of short steps, single solvent, simple post-treatment, wide raw material source, low price, low comprehensive cost and the like.
Photo-on-Demand Synthesis of Chloroformates with a Chloroform Solution Containing an Alcohol and Its One-Pot Conversion to Carbonates and Carbamates
Liang, Fengying,Suzuki, Yuto,Tsuda, Akihiko,Yanai, Masaki
, (2020/04/21)
Chloroformates are key reagents for synthesizing carbonates and carbamates. The present study reports a novel photo-on-demand in situ synthesis of chloroformates with a CHCl3 solution containing a primary alkyl alcohol. It further allowed the one-pot synthesis of carbonates and carbamates through subsequent addition of alcohols or amines, respectively.
Method for preparing ethyl chloroformate
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Paragraph 0017-0041, (2019/04/17)
The invention provides a method for preparing ethyl chloroformate, and relates to the technical field of organic matter synthesis. The method for preparing the ethyl chloroformate includes filling reaction towers with 45-55 L of ethyl alcohol; simultaneously stirring and cooling the ethyl alcohol in the reaction towers until the temperature of the ethyl alcohol reaches 3-6 DEG C, filling the reaction towers with phosgene at the flow velocity of 25-35 m/h, to be more specific, heating the reaction towers until the temperatures of the reaction towers reach 12-20 DEG C when the reaction towersstart to be filled with the phosgene, filling the reaction towers with the phosgene for the phosgene filling time of 2-2.5 h, continuing to carry out stirring reaction for 0.6-1 h after the reactiontowers finish being filled with the phosgene, and collecting products. The reaction towers are provided with stirrers, brine cooling reflux condensers, thermometers, gas leading-in openings and tail gas exhaust openings. The method for preparing the ethyl chloroformate has the advantages of little side reaction, high ethyl chloroformate reaction yield and high product purity.
Discovery of (3-Benzyl-5-hydroxyphenyl)carbamates as new antitubercular agents with potent in vitro and in vivo efficacy
Cheng, Ya-Juan,Liu, Zhi-Yong,Liang, Hua-Ju,Fang, Cui-Ting,Zhang, Niu-Niu,Zhang, Tian-Yu,Yan, Ming
, (2019/06/07)
A series of 3-amino-5-benzylphenol derivatives were designed and synthesized. Among them, (3-benzyl-5-hydroxyphenyl)carbamates were found to exert good inhibitory activity against M. tuberculosis H37Ra, H37Rv and clinically isolated multidrug-resistant M. tuberculosis strains (MIC = 0.625-6.25 μg/mL). The privileged compounds 3i and 3l showed moderate cytotoxicity against cell line A549. Compound 3l also exhibited potent in vivo inhibitory activity on a mouse infection model via the oral administration. The results demonstrated 3-hydroxyphenylcarbamates as a class of new antitubercular agents with good potential.
Benzoxazin-4-ones as novel, easily accessible inhibitors for rhomboid proteases
Yang, Jian,Barniol-Xicota, Marta,Nguyen, Minh T.N.,Ticha, Anezka,Strisovsky, Kvido,Verhelst, Steven H.L.
supporting information, p. 1423 - 1427 (2018/03/06)
Rhomboid proteases form one of the most widespread intramembrane protease families. They have been implicated in variety of human diseases. The currently reported rhomboid inhibitors display some selectivity, but their construction involves multistep synthesis protocols. Here, we report benzoxazin-4-ones as novel inhibitors of rhomboid proteases with a covalent, but slow reversible inhibition mechanism. Benzoxazin-4-ones can be synthesized from anthranilic acid derivatives in a one-step synthesis, making them easily accessible. We demonstrate that an alkoxy substituent at the 2-position is crucial for potency and results in low micromolar inhibitors of rhomboid proteases. Hence, we expect that these compounds will allow rapid synthesis and optimization of inhibitors of rhomboids from different organisms.
Bis-Acetyl Carbazole: A Photoremovable Protecting Group for Sequential Release of Two Different Functional Groups and Its Application in Therapeutic Release
Venkatesh, Yarra,Nandi, Surajit,Shee, Maniklal,Saha, Biswajit,Anoop, Anakuthil,Pradeep Singh
, p. 6121 - 6130 (2017/11/15)
In this paper, we present fluorescent photoremovable protecting groups (FPRPG) based on bis-acetyl carbazole for the release of two different functional groups such as carboxylic acids, alcohols, thiols, and amines in a sequential fashion. Dual-arm caged bis-acetyl carbazoles with different combinations of two unlike functional groups were synthesized. Photophysical studies showed that caged bis-acetyl carbazoles are blue fluorescent and their emission properties are sensitive to the environment. Sequential photorelease of two different functional groups by bis-acetyl carbazole was analyzed by HPLC, UV and emission spectroscopy. The mechanism of the dual release by bis-acetyl carbazole was investigated and supported by TD-DFT calculations. To demonstrate the applicability of the dual release ability of bis-acetyl carbazole FPRPG, we synthesized a drug delivery system (DDS) in which one arm of bis-acetyl carbazole is linked to the carboxylic functional group of chlorambucil (CBL) and the other arm is attached to the hydroxyl group of ferulic acid ethyl ester (FAEE). In vitro studies showed that our DDS presents excellent properties such as photoregulated dual drug delivery, cellular uptake, and biocompatibility.
Study of the Reaction Cl + Ethyl Formate at 700-950 Torr and 297 to 435 K: Product Distribution and the Kinetics of the Reaction C2H5OC(=O) → CO2 + C2H5
Kaiser
, p. 3414 - 3423 (2016/07/06)
The kinetics and mechanism of the reaction of atomic chlorine with ethyl formate [Cl + CH3CH2O(C=O)H, reaction 1] have been examined. These experiments were performed at pressures of 760-950 Torr and temperatures from 297 to 435 K. Reactants and products were quantified by gas chromatography-flame ionization detector (GC/FID) analysis. The initial mixture contained ethyl formate, Cl2, and N2. Cl atoms were generated by UV photolysis of this initial mixture at 360 nm, which dissociates Cl2. The rate constant of reaction 1 was measured at 297 K relative to that of the reaction Cl + C2H5Cl (reaction 2), yielding the rate constant ratio k1/k2 = 1.09 ± 0.05. The final products formed from reaction 1 are ethyl chloroformate, 1-chloroethyl formate, and 2-chloroethyl formate. These products result from the reactions with Cl2 of the three free radicals formed by H atom abstraction from ethylformate in reaction 1. Based on the molar yields of these three chlorinated products, the yields of the three radicals formed from reaction 1 at 297 K are (25 ± 3) mole percent of CH3CH2O(C=O); (67 ± 5) mole percent of CH3CHO(C=O)H; and (8 ± 2) mole percent of CH2CH2O(C=O)H. A second phase of this experiment measured the rate constant of the decarboxylation of the ethoxy carbonyl radical [CH3CH2O(C=O) → CO2 + C2H5, reaction 4] relative to the rate constant of its reaction with Cl2 [CH3CH2O(C=O) + Cl2 → CH3CH2O(C=O)Cl + Cl, reaction 3a]. Over the temperature range 297 to 404 K at 1 atm total pressure, this ratio can be expressed by k4/k3a = 1023.56±0.22 e-(12700±375)/RT molecules cm-3. Estimating the value of k3a (which has not been measured) based on similar reactions, the expression k4 = 5.8 × 1012 e-(12700)/RT s-1 is obtained. The estimated error of this rate constant is ± a factor of 2 over the experimental temperature range. This rate expression is compared with recent ab initio calculations of the decarboxylation of the analogous methoxy carbonyl radical.
In vitro radical scavenging and cytotoxic activities of novel hybrid selenocarbamates
Romano, Beatriz,Plano, Daniel,Encío, Ignacio,Palop, Juan Antonio,Sanmartín, Carmen
, p. 1716 - 1727 (2015/03/30)
Novel selenocyanate and diselenide derivatives containing a carbamate moiety were synthesised and evaluated in vitro to determine their cytotoxic and radical scavenging properties. Cytotoxic activity was tested against a panel of human cell lines including CCRF-CEM (lymphoblastic leukaemia), HT-29 (colon carcinoma), HTB-54 (lung carcinoma), PC-3 (prostate carcinoma), MCF-7 (breast adenocarcinoma), 184B5 (non-malignant, mammary gland derived) and BEAS-2B (non-malignant, derived from bronchial epithelium). Most of the compounds displayed high antiproliferative activity with GI50 values below 10 μM in MCF-7, CCRF-CEM and PC-3 cells. Radical scavenging properties of the new selenocompounds were confirmed testing their ability to scavenge DPPH and ABTS radicals. Based on the activity of selenium-based glutathione peroxidases (GPxs), compounds 1a, 2e and 2h were further screened for their capacity to reduce hydrogen peroxide under thiol presence. Results suggest that compound 1a mimics GPxs activity. Cytotoxic parameters, radical scavenging activity and ADME profile point to 1a as promising drug candidate.
1-(Hydroxyacetyl)pyrene a new fluorescent phototrigger for cell imaging and caging of alcohols, phenol and adenosine
Jana, Avijit,Saha, Biswajit,Ikbal, Mohammed,Ghosh, Sudip Kumar,Singh, N. D. Pradeep
, p. 1558 - 1566 (2013/02/26)
1-(Hydroxyacetyl)pyrene has been introduced as a new fluorescent phototrigger for alcohols and phenols. Alcohols and phenols were protected as their corresponding carbonate esters by coupling with fluorescent phototrigger, 1-(hydroxyacetyl)pyrene. Photophysical studies of caged carbonates showed that they all exhibited strong fluorescence properties. Irradiation of the caged carbonates by visible light (≥410 nm) in aqueous acetonitrile released the corresponding alcohols or phenols in high chemical (95-97%) and quantum (0.17-0.21) yields. The mechanism for the photorelease was proposed based on Stern-Volmer quenching experiments and solvent effect studies. Importantly, 1-(hydroxyacetyl)pyrene showed as a phototrigger for rapid photorelease of the biologically active molecule adenosine. In vitro biological studies revealed that 1-(hydroxyacetyl)pyrene has good biocompatibility, cellular uptake property and cell imaging ability. The Royal Society of Chemistry and Owner Societies 2012.