3140-73-6Relevant articles and documents
Understanding the effect of an amino group on the selective and ultrafast detection of TNP in water using fluorescent organic probes
Das, Prasenjit,Mandal, Sanjay K.
, p. 3288 - 3297 (2018)
We have designed and developed three single-molecule fluorescent probes differing in the number of amino groups, namely 5-((4,6-Diamino-1,3,5-triazin-2-yl)amino)isophthalic acid (H2ATAIA, 1), 5-((4-amino-6-methoxy-1,3,5-triazin-2-yl)amino)isophthalic acid (H2AMTAIA, 2) and 5-((4,6-dimethoxy-1,3,5-triazin-2-yl)amino)isophthalic acid (H2DMTAIA, 3), from cheap and readily available starting materials via simple procedures in high yields for demonstrating their application in highly selective and ultrafast sensing of 2,4,6-trinitrophenol (TNP) in water (slurry mode). Probes 1-3 have been characterized by various analytical techniques, such as melting point, FTIR, UV-vis and NMR (1H and 13C) spectroscopy and high resolution mass spectrometry (HRMS). It is quite evident that the effect of an amino group is more prominent compared to a methoxy group towards the selective detection of TNP over other potentially interfering nitro compounds. The detection limit for the diamino derivative was found to be 120 ppb compared to those with one amino or no amino group (0.8 ppm and 1.2 ppm, respectively). We also report the ideal real time detection of TNP through a contact mode or instant spot via paper strips. Spectral overlap, time-resolved fluorescence studies, quantum yield, Stern-Volmer plots, field emission scanning electron microscopy (FESEM) and DFT calculations have been used to establish their mechanism of action. Furthermore, competitive nitro-analyte tests demonstrate that the selectivity for TNP is more in 1 compared to 2 and 3. To the best of our knowledge, we have demonstrated for the first time molecular decoding of TNP based on the dual read-out identification scheme constructed from life-time and quantum yield. These probes have been found to be highly photostable in the presence of acidic TNP as well as recyclable without much loss of sensitivity up to five cycles. These results vividly depict that these are excellent candidates for environmental monitoring.
Synthesis of novel substituted 4,6-dimethoxy-N-phenyl-1,3,5-triazin-2-amine derivatives and their antibacterial and antifungal activities
Shinde, Ravindra S.,Salunke, Shridhar D.
, p. 4130 - 4134 (2015)
An efficient and convenient method of synthesis of 2-chloro-4,6-dimethoxy-1,3,5-triazine from cyanuric chloride in a short reaction time followed by synthesis of biological active novel substituted 4,6-dimethoxy-N-phenyl-1,3,5-triazin-2-amine (4a-x) using substituted anilines and heterocyclic amines, anhydrous K2CO3 in dry THF as solvent has been developed. Advantages of this methodology are short reaction time, excellent yield of products, easy work-up procedure. The synthesized compounds were confirmed by FT-IR, 1H NMR, mass spectral data. All the synthesized derivatives (4a-x) were screened for their antibacterial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa species and antifungal activities against Candida albicans MTCC 227, Candida glabrata NCIM 3236, Candida tropicalis NCIM 3110 and Aspergillus Niger NCIM 545 species.
An improved procedure for the large scale preparation of 2-chloro-4,6-dimethoxy-1,3,5-triazine
Cronin, Jason S.,Ginah, Francis O.,Murray, Angela R.,Copp, James D.
, p. 3491 - 3494 (1996)
A robust process for the preparation of multikilogram quantities of 2-chloro-4,6-dimethoxy-1,3,5-triazine (1) is described.
Synthesis and Antimicrobial Evaluation of Bis-morpholine Triazine Quaternary Ammonium Salts
Morandini, Andrea,Leonetti, Benedetta,Riello, Pietro,Sole, Roberto,Gatto, Vanessa,Caligiuri, Isabella,Rizzolio, Flavio,Beghetto, Valentina
supporting information, p. 3172 - 3176 (2021/08/03)
Efficient, environmentally and economically sustainable, and nontoxic antibacterial products are of global relevance in the fight against microorganism contamination. In this work, an easy and straightforward method for the synthesis of bis-morpholino triazine quaternary ammonium salts (bis-mTQAS) is reported, starting from 2,4,6-trichloro-1,3,5-triazine or 2,4-dichloro-6-methoxy-1,3,5-triazine and various N-alkylmorpholines. Bis-mTQAS were tested as antimicrobials against Gram-negative and Gram-positive bacterial strains. The best-performing bis-mTQAS were found to achieve total disinfection against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 at 50 and 400 μg/mL, respectively. Distinctively, bis-mTQAS with the highest antimicrobial efficiency had lowest cytotoxicity.
Solvent-Directed Click Reaction between Active Methylene Compounds and Azido-1,3,5-triazines
Yan, Ziqiang,Li, Yuanheng,Ma, Mingming
supporting information, p. 7204 - 7208 (2019/10/08)
A novel solvent-directed click reaction between active methylene compounds and azido-1,3,5-triazines has been developed. In aqueous solution, the regiospecific trisubstituted 1,2,3-triazole products are quickly synthesized in high yields under mild conditions and easy to separate without column chromatography. This click reaction is controlled by the protonation of a nitrogen anion intermediate, and the postulated mechanism is substantiated by DFT calculations.
Diazo-Transfer Reagent 2-Azido-4,6-dimethoxy-1,3,5-triazine Displays Highly Exothermic Decomposition Comparable to Tosyl Azide
Green, Sebastian P.,Payne, Andrew D.,Wheelhouse, Katherine M.,Hallett, Jason P.,Miller, Philip W.,Bull, James A.
, p. 5893 - 5898 (2019/05/06)
2-Azido-4,6-dimethoxy-1,3,5-triazine (ADT) was reported recently as a new "intrinsically safe" diazo-transfer reagent. This assessment was based on differential scanning calorimetry data indicating that ADT exhibits endothermic decomposition. We present DSC data on ADT that show exothermic decomposition with an initiation temperature (Tinit) of 159 °C and an enthalpy of decomposition (?HD) of ?1135 J g-1 (?207 kJ mol-1). We conclude that ADT is potentially explosive and must be treated with caution, being of comparable exothermic magnitude to tosyl azide (TsN3). A maximum recommended process temperature for ADT is 55 °C.
Intrinsically Safe and Shelf-Stable Diazo-Transfer Reagent for Fast Synthesis of Diazo Compounds
Xie, Shibo,Yan, Ziqiang,Li, Yuanheng,Song, Qun,Ma, Mingming
, p. 10916 - 10921 (2018/09/17)
We report a crystalline compound 2-azido-4,6-dimethoxy-1,3,5-triazine (ADT) as an intrinsically safe, highly efficient, and shelf-stable diazo-transfer reagent. Because the decomposition of ADT is an endothermal process (ΔH = 30.3 kJ mol-1), ADT is intrinsically nonexplosive, as proved by thermal, friction, and impact tests. The diazo-transfer reaction based on ADT gives diazo compounds in excellent yields within several minutes at room temperature. ADT is very stable upon >1 year storage under air at room temperature.
Potent triazine-based dehydrocondensing reagents substituted by an amido group
Kunishima, Munetaka,Kato, Daiki,Kimura, Nobu,Kitamura, Masanori,Yamada, Kohei,Hioki, Kazuhito
supporting information, p. 1897 - 1903 (2016/10/05)
This study describes the synthesis of triazine-based dehydrocondensing reagents substituted by amido substituents and demonstrates their efficiency for dehydrocondensing reactions in MeOH and THF. N-Phenylbenzamido-substituted chlorotriazine is readily converted to a stable, non-hygroscopic triazinylammonium-based dehydrocondensing reagent that is superior to 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) in terms of its reactivity in dehydrocondensing reactions.
Hydrazino-methoxy-1,3,5-triazine derivatives' excellent corrosion organic inhibitors of steel in acidic chloride solution
El-Faham, Ayman,Osman, Sameh M.,Al-Lohedan, Hamad A.,El-Mahdy, Gamal A.
, (2016/07/07)
The corrosion inhibition performance of 2-hydrazino-4,6-dimethoxy-1,3,5-tirazine (DMeHT), 2,4-dihydrazino-6-methoxy-1,3,5-triaizine (DHMeT), and 2,4,6-tridydrazino-1,3,5-triaizne (TH3 ) on steel corrosion in acidic media was examined using electrochemical techniques. The results showed 2,4-Ddihydrazino-6-methoxy-1,3,5-triaizine (DHMeT) gave the best corrosion protection performance among the other hydrazino derivatives even at a low concentration of 25 ppm (95%). The number of hydrazino groups play an important role in the corrosion inhibition, where the two hydrazine groups increased the electrostatic interactions between the protonated tested compounds, the negatively charged steel surface resulted from the adsorption of the chloride anions, and the presence of the methoxy group made the compound more reliable for formation of film protection on the surface of steel through the lone pair of oxygen atoms. Electrochemical Impedance Spectroscopy (EIS) measurements suggested that the corrosion process of steel in presence of the hydrazino-s-triazine derivatives (TH3 , DMeHT and DHMeT) were being controlled by the charge transfer reaction. Polarization curves indicated that the examined TH3 , DMeHT and DHMeT behaved as mixed type inhibitors.
METHOD FOR THE INDUSTRIAL PRODUCTION OF 2-HALO -4,6-DIALKOXY-1,3,5-TRIAZINES AND THEIR USE IN THE PRESENCE OF AMINES
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Page/Page column 34, (2016/07/27)
A method for stabilization of collagen matrices and of condensation of natural and synthetic polymers that uses 2-halo-4, 6-dialkoxy-1, 3, 5-triazines in the presence of one or more amines as activating agents for reactions of crosslinking, condensation, grafting, and curing of collagen matrices, cellulose, modified celluloses, polysaccharides, acid unsaturated polymers, and chiral and non-chiral amines, etc. Forming an integral part of the present invention is also the method for production on an industrial scale of 2-halo-4, 6-dialkoxy-1, 3, 5-triazines.
