22719-87-5

Basic information

• Product Name: 4-chlorophenyl ethyl carbonate
• CAS NO: 22719-87-5
• Molecular Formula: C₉H₉ClO₃
• Molecular Weight: 200.619
• Mol File: 22719-87-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 274°C at 760 mmHg
• Flash Point: 115.2°C
• Density: 1.239g/cm³
• Vapor Pressure: 0.00555mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: 4-chlorophenyl ethyl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chlorophenyl ethyl carbonate(22719-87-5)
• EPA Substance Registry System: 4-chlorophenyl ethyl carbonate(22719-87-5)

Safety Data

• Hazardous Substances Data: 22719-87-5(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 7693-45-0 4-Chlorophenyl chloroformate 
• 24573-38-4 4-chlorophenolate 
• 134906-71-1 O-ethyl S-(2,4-dinitrophenyl) thiocarbonate 
• 107701-37-1 O-ethyl S-(4-nitrophenyl) thiocarbonate 
• 153621-93-3 O-Ethyl S-(2,4,6-trinitrophenyl) thiocarbonate 
• 17284-90-1 ethyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate 
• 106-48-9 4-chloro-phenol 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 106-48-9 4-chloro-phenol 

Relevant articles and documents

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.

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.