18938-16-4

Basic information

• Product Name: 4-hydroxy-benzoic acid ethyl ester; deprotonated form
• Synonyms: 4-hydroxy-benzoic acid ethyl ester; deprotonated form
• CAS NO: 18938-16-4
• Molecular Weight: 165.169
• Mol File: 18938-16-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4-hydroxy-benzoic acid ethyl ester; deprotonated form(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-benzoic acid ethyl ester; deprotonated form(18938-16-4)
• EPA Substance Registry System: 4-hydroxy-benzoic acid ethyl ester; deprotonated form(18938-16-4)

Safety Data

• Hazardous Substances Data: 18938-16-4(Hazardous Substances Data)

Upstream product

• 74104-89-5 p-nitrophenyl picolinate 
• 942619-29-6 C₁₈H₁₆O₄ 
• 124-40-3 dimethyl amine 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 61921-33-3 p-nitrocinnamoyl chloride 
• 102-92-1 cinnamoyl chloride 
• 1325726-20-2 C₁₆H₁₄O₄S 
• 1268380-09-1 phenyl 4-ethoxycarbonyl phenyl 
• 1005-56-7 phenylcarbonochloridothioate 
• 7471-31-0 4-(ethoxycarbonyl)phenyl benzoate 
• 16331-64-9 ethanolate 

Downstream Products

• 20350-26-9 2,4-dinitrophenolate 
• 113038-29-2 4-(Diphenoxy-phosphoryloxy)-benzoic acid ethyl ester 

Relevant articles and documents

Acid dissociation constants of phenols and reaction mechanism for the reactions of substituted phenyl benzoates with phenoxide anions in absolute ethanol

Acid dissociation constants of 10 substituted phenols have been measured by a kinetic method together with second-order rate constants for the reactions of aryl benzoates (X-C6H4CO-OC6H4-Y) with Z-substituted phenoxide (Z-C6H4O-) and EtO- in absolute ethanol at 25.0 ± 0.1°C. The kinetic results support a stepwise mechanism for the present acyl-transfer reaction.

Kinetic Study on Nucleophilic Substitution Reactions of O-Phenyl O-Y-substituted-Phenyl Thionocarbonates with 1,8-Diazabicyclo[5.4.0]undec-7-ene in Acetonitrile

Second-order rate constants (kN) for nucleophilic substitution reactions of O-phenyl O-Y-substituted-phenyl thionocarbonates (4a–4k) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN at 25.0 ± 0.1°C are reported. The reactivity of 4a–4k decreases as basicity of the leaving group increases except O-2,4-dinitrophenyl O-phenyl thionocarbonate (4a), which is less reactive than O-3,4-dinitrophenyl O-phenyl thionocarbonate (4b) although the former possesses 2 pKa units less basic nucleofuge than the latter. The Br?nsted-type plot for the reactions of 4b–4k is linear with βlg = ?0.50, a typical βlg value for reactions reported to proceed through a concerted mechanism. The Hammett plot correlated with σY? constants for the reactions of 4b–4k results in a better linear correlation than that correlated with σYo constants. Besides, the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρY = 2.12, r = 0.68 and R2 = 0.990, indicating that a negative charge develops partially on the O atom of the leaving group in the rate-determining step (RDS). Thus, the reactions have been concluded to proceed through a forced concerted mechanism. Effects of steric hindrance on reactivity and reaction mechanism are also discussed in detail.

Alkaline hydrolysis of Y-substituted phenyl phenyl thionocarbonates: Effect of changing electrophilic center from C=O to C=S on reactivity and mechanism

Second-order rate constants (kOH-) have been measured spectrophotometrically for reactions of Y-substituted phenyl phenyl thionocarbonates (4a-i) with OH- in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. The ksu