22719-84-2

Upstream product

• 17284-90-1 ethyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate 
• 150-76-5 4-methoxy-phenol 
• 123-31-9 hydroquinone 
• 541-41-3 chloroformic acid ethyl ester 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1609-47-8 diethyl dicarbonate 
• 29368-59-0 p-methoxyphenolate 
• 153621-93-3 O-Ethyl S-(2,4,6-trinitrophenyl) thiocarbonate 
• 107701-37-1 O-ethyl S-(4-nitrophenyl) thiocarbonate 
• 134906-71-1 O-ethyl S-(2,4-dinitrophenyl) thiocarbonate 

Downstream Products

• 35031-01-7 ethyl 4-hydroxy-2-methoxybenzoate 
• 22775-40-2 ethyl 2-hydroxy-5-methoxybenzoate 
• 15174-02-4 4-hydroxy-2-nitroanisole 
• 98083-21-7 3-amino-4-methoxyphenyl ethyl carbonate 
• 1428848-00-3 ethyl 4-methoxy-3-(methylsulfonamido)phenyl carbonate 
• 1428848-02-5 N-(5-hydroxy-2-methoxyphenyl)-N-(2-morpholinoethyl)methanesulfonamide 
• 1428848-01-4 ethyl 4-methoxy-3-(N-(2-morpholinoethyl)-methylsulfonamido)phenyl carbonate? 
• 1428847-98-6 (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((4-methoxy-3-(N-(2-morpholinoethyl)methylsulfonamido)phenoxy)carbonyloxy)ethyl)pyridine 1-oxide? 

Relevant academic research and scientific papers

Concerted mechanisms of the reactions of ethyl S-aryl thiocarbonates with substituted phenoxide ions

The reactions of 4-nitrophenyl, 2,4-dinitrophenyl, and 2,4,6- trinitrophenyl O-ethyl thiolcarbonates with substituted phenoxide ions are subjected to a kinetic study in water, 25.0 °C, ionic strength 0.2 M (KCl). By following the reactions spectrophotometrically, pseudo-first-order rate coefficients (k(obsd)) are found under excess of the nucleophile. Plots of k(obsd) vs phenoxide anion concentration at constant pH are linear, with the slope (k(N)) independent of pH. The Bronsted-type plots (log k(N) vs pK(a) of the phenols) are linear with slopes β = 0.92, 0.77, and 0.61 for the reactions of the 4-nitrophenyl, 2,4-dinitrophenyl, and 2,4,6-trinitrophenyl derivatives, respectively. For these reactions, a concerted mechanism is proposed since the slope values are similar to those found in the concerted phenolysis of aryl acetates; the slope magnitudes are not consistent with a stepwise mechanism where the formation of a tetrahedral intermediate is rate limiting. Our results are in line with the finding that the reactions of the 2,4-dinitrophenyl and 2,4,6-trinitrophenyl derivatives with secondary alicyclic amines in water are concerted. In contrast, the reactions of the same substrates with pyridines are stepwise, which means that substitution of a pyridine moiety in a tetrahedral intermediate with a benzenethio group by a phenoxy group destabilizes the intermediate.

Alkyl and aryl 4,5-dichloro-6-oxopyridazin-1(6 H)-carboxylates: A practical alternative to chloroformates for the synthesis of symmetric and asymmetric carbonates

Symmetric and asymmetric carbonates were synthesized by using alkyl or aryl 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates. Five aryl 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates were converted into the corresponding diaryl carbonates in good to excellent yields by treatment with potassium carbonate in refluxing THF. When the 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates were treated with aliphatic or aromatic alcohols in the presence of potassium tert-butoxide in toluene at room temperature, they gave the corresponding symmetric or asymmetric carbonates in moderate to excellent yields. Alkyl and aryl 4,5-dichloro-6-oxopyridazin-1(6H)-carboxylates are therefore efficient, stable, and ecofriendly alternatives to chloroformates.

Synthesis of organic carbonates with alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and ROH/AlCl3under ambient condition

We demonstrated the synthesis of organic carbonates using alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates and alcohol in the presence of aluminum chloride. Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates were reacted with alcohol in the presence of AlCl3 in toluene at room temperature to afford the corresponding unsymmetric and symmetric organic carbonates in good to excellent yields. These are efficient and convenient processes. Alkyl/aryl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylates are solid, stable and non-toxic CO2/CO2R(Ar) source. It is noteworthy that the reaction is carry out under an ambient and acidic conditions, the easy-to prepare and readily available starting materials and the quantitative isolation of reusable 4,5-dichloropyridazin-3(2H)-one.

A new versatile synthesis of esters from Grignard reagents and chloroformates

Cross-coupling reactions of chloroformates with organocopper reagents, derived from Grignard reagents, cuprous bromide and lithium bromide, provide a rapid and straightforward method for the synthesis of esters. Georg Thieme Verlag Stuttgart.

A new, mild, general and efficient route to aryl ethyl carbonates in solvent-free conditions promoted by magnesium perchlorate

A new, general and mild method for the direct synthesis of aryl and alkyl ethyl carbonates promoted by a Lewis acid is reported. The reaction proceeds smoothly with diethyl dicarbonate in the presence of Mg(ClO4) 2, a specific activator of 1,3-dicarbonyl compounds, and shows general applicability. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.