19183-08-5

Upstream product

• 619-45-4 4-methoxycarbonyl aniline 

Downstream Products

• 1261981-75-2 methyl 4-(3-hydroxypyridin-2-yl)benzoate 
• 36078-99-6 2-(4-(methoxycarbonyl)phenyl)benzo[b]furan 
• 485321-10-6 4-(indol-2-yl)benzoic acid methyl ester 
• 53355-26-3 4-(5-methyl-furan-2-yl)-benzoic acid methyl ester 
• 53355-25-2 methyl 4-(2-furanyl)benzoate 

Relevant academic research and scientific papers

Frozen aryldiazonium chlorides in radical reactions with alkenes and arenes

Frozen aryldiazonium chlorides have been investigated in radical alkene and arene functionalizations. Through freezing at – 84 °C, aryldiazonium chlorides, which otherwise show significant decomposition in aqueous solution after several hours at room temp

Changes in metabolic chemical reporter structure yield a selective probe of O -GlcNAc modification

Metabolic chemical reporters (MCRs) of glycosylation are analogues of monosaccharides that contain bioorthogonal functionalities and enable the direct visualization and identification of glycoproteins from living cells. Each MCR was initially thought to report on specific types of glycosylation. We and others have demonstrated that several MCRs are metabolically transformed and enter multiple glycosylation pathways. Therefore, the development of selective MCRs remains a key unmet goal. We demonstrate here that 6-azido-6-deoxy-N- acetyl-glucosamine (6AzGlcNAc) is a specific MCR for O-GlcNAcylated proteins. Biochemical analysis and comparative proteomics with 6AzGlcNAc, N-azidoacetyl-glucosamine (GlcNAz), and N-azidoacetyl-galactosamine (GalNAz) revealed that 6AzGlcNAc exclusively labels intracellular proteins, while GlcNAz and GalNAz are incorporated into a combination of intracellular and extracellular/lumenal glycoproteins. Notably, 6AzGlcNAc cannot be biosynthetically transformed into the corresponding UDP sugar-donor by the canonical salvage-pathway that requires phosphorylation at the 6-hydroxyl. In vitro experiments showed that 6AzGlcNAc can bypass this roadblock through direct phosphorylation of its 1-hydroxyl by the enzyme phosphoacetylglucosamine mutase (AGM1). Taken together, 6AzGlcNAc enables the specific analysis of O-GlcNAcylated proteins, and these results suggest that specific MCRs for other types of glycosylation can be developed. Additionally, our data demonstrate that cells are equipped with a somewhat unappreciated metabolic flexibility with important implications for the biosynthesis of natural and unnatural carbohydrates.

Radical arylation of phenols, phenyl ethers, and furans

Radical arylations of parasubstituted phenols and phenyl ethers proceeded with good regioselectivity at the ortho position with respect to the hydroxy or alkoxy group. The reactions were conducted with arenediazonium salts as the aryl radical source, titaniumACHTUNGTRENUNG(III) chloride as the reductant, and diluted hydrochloric acid as the solvent. Substituted biaryls were obtained from hydroxy- and alkoxy-substituted benzylamines, phenethylamines, and aromatic amino acids. The methodology described offers a fast, efficient, and cost-effective new access todiversely functionalized biphenyl alcohols and ethers. Free phenolic hydroxyl groups, aromatic and aliphatic amines, as well as amino acid substructures, are well tolerated. Two examples for the applicability of the methodology are the partial synthesis of a b-secretase inhibitor and the synthesis of a calciumchannel modulator

Synthesis and physical properties of ferrocene derivatives (XXII): Monosubstituted ferrocene derivatives containing biphenyl group in the mesogenic one

The monosubstituted ferrocene derivatives containing biphenyl group in mesogenic one, -[4-(4-methoxybiphenoxy carbonyl) phenoxycarbonyl] alkyl 4-ferrocenylbenzoate, have been synthesized by changing the carbon atoms number of the flexible spacer. The anal

OPEN CHAIN NITROGEN COMPOUNDS. PART XIII. 1-ARYL-3-ARYLTHIOMETHYL-3-METHYLTRIAZENES AND 3-(ARYLAZO)-1,3-THIAZOLIDINES

Reaction of 3-acetoxymethyl-1-aryl-3-methyltriazenes with sodium thiophenolate or thiocresolate in anhydrous dimethylformamide affords a new series of 3-arylthiomethyltriazenes (2).Ar-S-CH2-NMe-N=N-Ar'.These triazenes are remarkably labile in aqueous buff

USE OF CURRENT-LESS POTENTIAL-TIME CURVES FOR DETERMINIG THE RATE CONSTANTS OF AZO COPULATION REACTIONS

The method of current-less potential-time curves was applied to the determination of rate constants for five azo copulation reactions, where the dyes formed need not to be soluble in the reaction medium.The results are compared with those from the literature.

Open-chain nitrogen compounds. Part IV. Synthesis of 5-hydroxy-1,2,3-triazoles from 1-aryl-3-(ethoxycarbonylmethyl)triazenes: a new route to α-diazo-N-arylacetamides

A series of triazenes of type ArN=N-NH-CH2CO2Et, N-arylazoglycine ethyl esters, have been prepared by coupling the arene diazonium salt, ArN2+*X-, with ethyl glycinate, NH2CH2CO2Et; an electron-withdrawing substituent, e.g.NO2, CN, CO2R, and Cl, in the ortho or para position of the aryl group is essential for efficient coupling.The p-substituted arylazoglycine ethyl esters cyclize when treated with alcoholic potassium hydroxide to afford the potassium salts of the 1-aryl-5-hydroxy-1,2,3-triazoles, which can be obtained free by acidification of the potassium salt solution with acetic acid.Reaction of the potassium salts with acetic anhydride yields the 1-aryl-5-acetoxy-1,2,3-triazoles.The 5-hydroxytriazoles, when heated in ethanol, rearrange to α-diazoacetanilides, ArNH*COCHN2.The diazoamides can be obtained in low yield directly from the triazenes by prolonged refluxing in ethanol. o-Substituted aryltriazenes do not cyclize under the same conditions but fragment to the arylamine.

Substituent Effects on 13C and 15N Chemical Shifts in Triazenes Studied by Principal Components Multivariate Data Analysis

Principal components analysis was applied to the 13C and 15N chemical shift data on a series of fifteen 1-(para-substituted-phenyl)-3-acetyl-3-methyltriazenes.It was found that the halogen-substituted triazenes formed a class, based on substituent effects, which was different from the remaining eleven triazenes.A one-component model described the halogen class, whereas a two-component model was necessary for a description of the second class.In the second class, substituent tended to cluster to form groups depending on their electronic character.