Category: 1003-21-0

Volpe, Andrea; Natali, Mirco; Graiff, Claudia; Sartorel, Andrea; Tubaro, Cristina; Bonchio, Marcella published the artcile< Novel iridium complexes with N-heterocyclic dicarbene ligands in light-driven water oxidation catalysis: photon management, ligand effect and catalyst evolution>, Recommanded Product: 5-Bromo-1-methyl-1H-imidazole, the main research area is imidazolylidene silver dicarbene complex transmetalation cyclopentadienyl iridium chloride; iridium imidazolylidene dicarbene complex preparation catalyst water oxidation kinetics; crystal structure imidazolylidene cyclopentadienyliridium dicarbene complex; mol structure imidazolylidene cyclopentadienyliridium dicarbene complex.

Ir complexes [IrClCp*diNHC]PF6, with N-heterocyclic dicarbene (diNHC) and pentamethylcyclopentadienyl (Cp*) ligands, were studied in light driven H2O oxidation catalysis within the Ru(bpy)32+/S2O82- cycle (bpy = 2,2′-bipyridine). In particular, the effect of different diNHC ligands was evaluated by employing the complex 1a (diNHC = 1,1′-dimethyl-3,3′-ethylenediimidazol-2,2′-diylidene) and the novel and structurally characterized 2 (diNHC = 1,1′-dimethyl-3,3′-ethylene-5,5′-dibromodiimidazol-2,2′-diylidene) and 3 (diNHC = 1,1′-dimethyl-3,3′-ethylene-dibenzimidazol-2,2′-diylidene). The presented results include: (i) a photon management anal. of the 1a/Ru(bpy)32+/S2O82- system, revealing two regimes of O2 evolution rate, being dependent on the light intensity at low photon flux, where the system reaches an overall quantum yield up to 0.17 ± 0.01 (quantum efficiency 34 ± 2%), while being independent of light intensity at high photon flux thus indicating a change of limiting step; (ii) a trend of O2 evolution activity that follows the order 1a > 2 > 3 both under low and high photon flux conditions, with the reactivity that is favored by the electron donating nature of the diNHC ligand, quantified from the carbene C chem. shift; (iii) an analogous trend also in the bimol. rate constants of electron transfer kET from the Ir species to photogenerated Ru(bpy)33+, with kET values in the range 4.2-6.1 × 104 M-1 s-1, thus implying a significant reorganization energy to the Ir sphere; (iv) the evolution of 1a, as the most active Ir species in the series, to mononuclear Ir species with lower mol. weight and originating from oxidative transformation of the organic ligand scaffold, as proven by converging UV-visible, MALDI-MS and 1H-NMR evidences. These results can be used for the further design and engineering of novel catalysts.

Dalton Transactions published new progress about Carbene complexes Role: CAT (Catalyst Use), PRP (Properties), SPN (Synthetic Preparation), USES (Uses), PREP (Preparation) (cyclopentadienyl Ir complexes). 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Recommanded Product: 5-Bromo-1-methyl-1H-imidazole.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Gilmore, John L.; Xiao, Hai-Yun; Dhar, T. G. Murali; Yang, Michael G.; Xiao, Zili; Xie, Jenny; Lehman-McKeeman, Lois D.; Gong, Lei; Sun, Huadong; Lecureux, Lloyd; Chen, Cliff; Wu, Dauh-Rurng; Dabros, Marta; Yang, Xiaoxia; Taylor, Tracy L.; Zhou, Xia D.; Heimrich, Elizabeth M.; Thomas, Rochelle; McIntyre, Kim W.; Borowski, Virna; Warrack, Bethanne M.; Li, Yuwen; Shi, Hong; Levesque, Paul C.; Yang, Zheng; Marino, Anthony M.; Cornelius, Georgia; D’Arienzo, Celia J.; Mathur, Arvind; Rampulla, Richard; Gupta, Anuradha; Pragalathan, Bala; Shen, Ding Ren; Cvijic, Mary Ellen; Salter-Cid, Luisa M.; Carter, Percy H.; Dyckman, Alaric J. published the artcile< Identification and preclinical pharmacology of ((1R,3S)-1-amino-3-((S)-6-(2-methoxyphenethyl)-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopentyl)methanol (BMS-986166): a differentiated sphingosine-1-phosphate receptor 1 (S1P1) modulator advanced into clinical trials>, HPLC of Formula: 1003-21-0, the main research area is sphingosine 1 phosphate receptor pharmacokinetics arthritis antiarthritic multiple sclerosis; crystal structure.

Recently, our research group reported the identification of BMS-986104 (2) as a differentiated S1P1 receptor modulator. In comparison to fingolimod (1), a full agonist of S1P1 currently marketed for the treatment of relapse remitting multiple sclerosis (RRMS), 2 offers several potential advantages having demonstrated improved safety multiples in preclin. evaluations against undesired pulmonary and cardiovascular effects. In clin. trials, 2 was found to exhibit a pharmacokinetic half-life (T1/2) longer than that of 1, as well as a reduced formation of the phosphate metabolite that is required for activity against S1P1. Herein, we describe our efforts to discover highly potent, partial agonists of S1P1 with a shorter T1/2 and increased in vivo phosphate metabolite formation. These efforts culminated in the discovery of ((1R,3S)-1-amino-3-((S)-6-(2-methoxyphenethyl)-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopentyl)methanol [1883345-06-9] (BMS-986166, 14a), which was advanced to human clin. evaluation. The pharmacokinetic/pharmacodynamic (PK/PD) relationship as well as pulmonary and cardiovascular safety assessments are discussed. Furthermore, efficacy of BMS-986166 in multiple preclin. models of autoimmune diseases are presented.

Journal of Medicinal Chemistry published new progress about Anti-multiple sclerosis agents. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, HPLC of Formula: 1003-21-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Wang, Xuan; Sun, Hui; Liu, Jiaxiang; Zhong, Wenge; Zhang, Mingqiang; Zhou, Hu; Dai, Dongcheng; Lu, Xiaojie published the artcile< Palladium-Promoted DNA-Compatible Heck Reaction>, Quality Control of 1003-21-0, the main research area is palladium promoted Heck reaction on DNA; DNA conjugated styrene acrylamide aryl iodide single strand DNA.

Optimal conditions for palladium-promoted Heck reaction on DNA were developed with good to excellent conversions. Versatility with either DNA-conjugated styrene/acrylamide or aryl iodide and a broad substrate scope of the corresponding coupling partners were established. Furthermore, robustness of the Heck reaction conditions on single-strand DNA and feasibility for DNA-encoded library production were demonstrated.

Organic Letters published new progress about Amides Role: SPN (Synthetic Preparation), PREP (Preparation). 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Quality Control of 1003-21-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Sakamoto, Takao; Kondo, Yoshinori; Suginome, Takashi; Ohba, Setsuya; Yamanaka, Hiroshi published the artcile< Palladium-catalyzed cross-coupling reaction of haloazoles with phenylsulfonylacetonitrile>, COA of Formula: C4H5BrN2, the main research area is palladium catalyzed cross coupling reaction haloazole; condensation haloazole phenylsulfonylacetonitrile; oxazoleacetonitrile phenylsulfonyl; thiazoleacetonitrile phenylsulfonyl; imidazoleacetonitrile phenylsulfonyl.

Condensation of halo-substituted 1,3-azoles (1,3-oxazoles, 1,3-thiazoles and imidazoles), e.g., I (R = Br), with phenylsulfonylacetonitrile under basic conditions was promoted by the catalytic action of tetrakis(triphenylphosphine)palladium(0) to give α-phenylsulfonyl-1,3-azoleacetonitriles, e.g., I (R = PhO2SCHCN). The adaptability of halogen atoms for the cross-coupling reaction was investigated. The reaction of 4-halo-1,2-azoles was also examined

Synthesis published new progress about Cross-coupling reaction. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, COA of Formula: C4H5BrN2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Grimmett, M. R. published the artcile< Product class 3: imidazoles>, Category: imidazoles-derivatives, the main research area is review imidazole preparation cyclization aromatization ring transformation.

A review. Methods for preparing imidazoles are reviewed including cyclization, ring transformations, aromatization and modification of substituents on existing imidazoles.

Science of Synthesis published new progress about Aromatization. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Category: imidazoles-derivatives.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Balaban, I. E.; Pyman, F. L. published the artcile< Bromo derivatives of 1-methylglyoxaline and the constitution of ""chloroxalmethylin"">, HPLC of Formula: 1003-21-0, the main research area is .

Bromination of 18 g. 1-methylglyoxaline in 60 cc. CHCl3 with 36 g. Br in 60 cc. CHCl3 at 5-10° gave 10.4 g. 2,4,5-tribromo-1-methylglyoxaline (I), m. 93-4.5° (Wallach, Ber. 16, 537, gives 88-9°), 0.49 g. (as picrate) of 4,5-dibromo-1-methylglyoxaline (II), m. 79-80°, and 23.3 g. (as picrate) of unchanged base. I.HCl, m. 190-200°, dissociates in H2O. I is recovered to the extent of 90% after heating with 1 mol. Na2SO3 in 20% aqueous solution for 5 hrs., 1% of II also being isolated. II was further prepared by heating 4,5-dibromo-1-methylglyoxaline with Me2SO4 and from (CONHMe)2 and PBr5 (7% and 11% with 1 and 2 mols. PBr5, resp.). II.HCl, crystallizing with 2 H2O, lost in vacuo over H2SO4, and then m. 179°; HNO3 salt, m. 153°; picrate, yellow, m. 148-9°, soluble in 6 parts hot EtOH or 30 parts boiling H2O. Methylation of 4(5)-bromoglyoxaline gives 51% III and 1.5% IV (ratio 34:1), separated by fractional crystallization of the picrates from EtOH. 5-Bromo-1-methylglyoxaline (III), b15 128°, m. 45-6°, deliquescent; HCl salt, needles with 0.5 H2O, lost at 100° and then m. 155°; HNO3 salt, anhydrous prisms, m. 155° (effervescence) soluble in 4 parts boiling H2O; H oxalate salt, needles with 0.5 H2O, lost in vacuo over H2SO4 and then m. 147°; picrate, yellow needles, m. 190°. The 4(?)-sulfonic acid, m. 284°, results in 78% yield; it is soluble in 55 parts boiling H2O, almost insoluble in cold H2O. Heating 0.38 g. of the acid with 5 cc. 30% H2SO4 for 3 hrs. at 170° gave 0.11 g. III (as picrate). The 4-nitro derivative (V) of III (80% yield), m. 180°, soluble in 85 parts boiling H2O; HCl salt, m. 155° and decomposed by H2O. V crystallines unchanged from aqueous picric acid. With aqueous Na2SO3 V yields 4-nitro-1-methylglyoxaline-5-sulfonic acid, m. 254° (decomposition); Na salt, fine needles. Hydrolysis of the acid by heating with 30% H2SO4 gives 4-nitro-1-methylglyoxaline; this establishes the orientation of these bases directly and of IV indirectly. III condenses with HCHO, by heating 6 hrs. at 130°, to give 5-bromo-2-hydroxymethyl-1-methylglyoxaline, m. 143° and soluble in 15 parts boiling H2O (yield, 42%); picrate, yellow needles, m. 165-6°. Reduction with HI and red P gives 1,2-dimethylglyoxaline. Either III or IV, heated with MeI, gives 4(5)-bromo-1,3-dimethylglyoxalinium iodide, m. 202-4°, soluble in 8 parts hot EtOH; distillation at 15 mm. and 235° gave 43% IV and some III. 4-Bromo-1-methylglyoxaline (IV) is an oil; HNO3 salt, prisms, m. 155°, soluble in about 3 parts boiling H2O; picrate, yellow needles, m. 179°, soluble in 7 parts hot EtOH. The 5(?)-sulfonic acid (yield, 77%) crystallines with 1 H2O, m. 256° (decomposition), soluble in 15 parts boiling H2O. The 5-nitro derivative (VI) (yield, 54%), m. 105°, soluble in 40 parts boiling H2O. Methylation of 7 g. 4(5)-bromo-5(4)nitroglyoxaline (VII), gave 1.7 g. VI and 1.4 g. unchanged material. Na2SO3 (20% aqueous solution) reacts with VII to give 4(5)-nitroglyoxaline-5(4)-sulfonic acid, decomposes 300° (yield, 88%); Na salt, fine needles. “”Chloroxalmethylin,”” prepared according to W., gives a HNO3 salt, m. 145° which, heated with concentrated H2SO4 1.5 hrs. at 100°, gives 5-chloro-4-nitro-1-methylglyoxaline, m. 147°, soluble in 40 parts boiling H2O; it is therefore 5-chloro-1-methylglyoxaline.

Journal of the Chemical Society, Transactions published new progress about 1003-21-0. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, HPLC of Formula: 1003-21-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Iida, Hiroki; Umebayashi, Naofumi; Yashima, Eiji published the artcile< Photoswitchable organocatalysis in acylation of alcohol using dithienylethene-linked azoles>, SDS of cas: 1003-21-0, the main research area is dithienylethene linked azole preparation photoswitchable organocatalyst acylation alc.

Three novel dithienylethenes bearing azole derivatives were synthesized and found to undergo reversible photocyclization of the dithienylethene units upon alternate irradiation with UV and visible light. Among them, the dithienylethene-linked imidazole and N-phenylimidazole exhibited a relatively high organocatalytic activity for the acylation of 2-decanol with acetic anhydride, and the catalytic activity of the dithienylethene-linked imidazole could be switched by reversible photoinduced cyclization/cycloreversion of the dithienylethene unit.

Tetrahedron published new progress about Acylation. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, SDS of cas: 1003-21-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Kochergin, P. M. published the artcile< Imidazole series. XV. Reaction products of N,N'-dimethyloxamide with pentahalo phosphorus compounds>, Recommanded Product: 5-Bromo-1-methyl-1H-imidazole, the main research area is .

14660a. Heating 2 kg. PCl5 with 550 g. (CONHMe)2 1-1.5 hrs. at 95-8° (exothermic initially), followed by further 1.6 hrs. after cessation of exothermic reaction, gave 50.6% 1-methyl-5-chloroimidazole, b9 84°, b10 87°, n22D 1.5120 (picrate m. 167-8°), unreacted amide, and 1-methyl-4,5-dichloroimidazole, m. 58.5-59° (picrate m. 130.5-1.5°; HCl salt m. 161-3°; nitrate m. 122°; sulfate m. 83-5°). Similar reaction of 11.6 g. (CONHMe)2 with 91.6 g. PCl5 and 250 ml. POCl3 in 0.5 hr. at 40-50°, then 1.5 hrs. at 100°, gave a low yield of 1-methyl-2,4,5-trichloroimidazole, m. 75.5-6° (petr. ether), 1-methyl-4,5-dichloroimidazole, isolated as the picrate, and 1-methyl-5-chloroimidazole. Heating 104 g. PBr5 with 14 g. (CONHMe)2 2.1 hrs. on a steam bath gave 19.6% 1-methyl-4,5-dibromoimidazole, m. 79-80° (picrate m. 149.5-50.5°), and 1-methyl-5-bromoimidazole, isolated as the picrate, m. 190-1°. Nitration of the mixed crude mono- and dibromo derivatives with mixed acid 2 hrs. at 100° gave 1-methyl-4-nitro-5-bromoimidazole, m. 180-1°. Heating (CONHMe)2 with PBr5 in POCl3 in 1 hr. at 60-70° and 2 hrs. at reflux gave 1-methyl-2,4,5-tribromoimidazole, m. 93-4°, 1-methyl-4,5-dibromoimidazole, and 1-methyl-5-bromoimidazole, isolated as the picrate.

Zhurnal Obshchei Khimii published new progress about Group 15 element halides, phosphorus halides. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Recommanded Product: 5-Bromo-1-methyl-1H-imidazole.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Vitale, Paola; D’Anna, Francesca; Ferrante, Francesco; Rizzo, Carla; Noto, Renato published the artcile< π-Conjugated diimidazolium salts: rigid structure to obtain organized materials>, Recommanded Product: 5-Bromo-1-methyl-1H-imidazole, the main research area is pi conjugated diimidazolium salt organized material.

Phenylene ethynylene based diimidazolium salts differing in the alkyl chain length borne on the imidazolium ion and anion nature were synthesized. Their properties were studied both in solution and in the solid state. Salts obtained were able to aggregate in organic solvent solution Aggregate formation was studied by performing concentration dependent measurements using UV-vis, fluorescence and Resonance Light Scattering. Furthermore, features of the aggregates were also investigated in the solid state by means of fluorescence and SEM measurements. Finally, D. Functional Theory calculations were performed to obtain insights into the interaction geometry in the salts investigated. Data collected evidence that aggregation processes are affected by a combined action of different factors derived from the nature of the salt and solvent. The above features also influence the morphol. of the aggregates as well as the ability of their thin films to give blue emission. On the whole, information gained could represent a useful starting point for applications of these salts in the optoelectronic field among others.

Physical Chemistry Chemical Physics published new progress about Aggregation. 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Recommanded Product: 5-Bromo-1-methyl-1H-imidazole.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

G-Dayanandan, Narendran; Scocchera, Eric W.; Keshipeddy, Santosh; Jones, Heather F.; Anderson, Amy C.; Wright, Dennis L. published the artcile< Direct Substitution of Arylalkynyl Carbinols Provides Access to Diverse Terminal Acetylene Building Blocks>, Electric Literature of 1003-21-0, the main research area is aryl propyne preparation reduction substitution arylalkynyl carbinol.

To develop next generation antifolates for the treatment of trimethoprim-resistant bacteria, synthetic methods were needed to prepare a diverse array of 3-aryl-propynes with various substitutions at the propargyl position. A direct route was sought whereby nucleophilic addition of acetylene to aryl carboxaldehydes would be followed by reduction or substitution of the resulting propargyl alc. The direct reduction, methylation, and dimethylation of these readily available alcs. provide efficient access to this uncommon functional array. In addition, an unusual silane exchange reaction was observed in the reduction of the propargylic alcs.

Organic Letters published new progress about Alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1003-21-0 belongs to class imidazoles-derivatives, and the molecular formula is C4H5BrN2, Electric Literature of 1003-21-0.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem