277313-11-8

Basic information

• Product Name: acetic acid-(2-chloro-4-methyl-phenyl ester)
• Synonyms: acetic acid-(2-chloro-4-methyl-phenyl ester)
• CAS NO: 277313-11-8
• Molecular Weight: 184.622
• Mol File: 277313-11-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: acetic acid-(2-chloro-4-methyl-phenyl ester)(CAS DataBase Reference)
• NIST Chemistry Reference: acetic acid-(2-chloro-4-methyl-phenyl ester)(277313-11-8)
• EPA Substance Registry System: acetic acid-(2-chloro-4-methyl-phenyl ester)(277313-11-8)

Safety Data

• Hazardous Substances Data: 277313-11-8(Hazardous Substances Data)

Upstream product

• 830-03-5 4-nitrophenol acetate 
• 6640-27-3 2-chloro-p-cresol 
• 108-24-7 acetic anhydride 
• 10186-94-4 3,4-dinitro-phenyl-acetate 

Downstream Products

• 7507-88-2 1-(3-chloro-2-hydroxy-5-methyl-phenyl)-ethanone 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 

Relevant articles and documents

Structure-reactivity correlations for reactions of substituted phenolate anions with acetate and formate esters

The reactions of substituted phenolate anions with m-nitrophenyl, p-nitrophenyl, and 3,4-dinitrophenyl formates follow nonlinear Br?nsted-type correlations that might be taken as evidence for a change in the rate-limiting step of a reaction that proceeds through a tetrahedral addition intermediate. However, the correlation actually represents two different Br?nsted lines that are defined by meta- and para-substituted phenolate anions and by meta- and para-substituted o-chlorophenolate anions. A concerted mechanism for both acetyl- and formyl-transfer reactions is supported by the absence of a detectable change in the Br?nsted slope at ΔpK = 0 for the attacking and leaving phenolate anions within each class of Br?nsted correlations. Regular increases in the dependence of log k on the pKa of the nucleophile with increasing pKa of the leaving group correspond to a positive interaction coefficient pxy = ?β1g/?(pKnuc) = ?βnuc/?(pK1g). The observation of two different Br?nsted lines for the reactions of substituted phenolate anions with phenyl acetates is attributed to a steric effect that decreases the rate of reaction of substituted o-chlorophenolate anions by 25-50%. The reactions of meta- and para-substituted phenolate and o-chlorophenolate anions with substituted phenyl acetate esters follow values of βnuc = 0.53-0.66 and -β1g = 0.50-0.63. The reactions of meta- and para-substituted phenolate anions with formate esters are ～ 103 times faster and follow smaller values of βnuc = 0.43-0.64 and -β1g = 0.31-0.48. However, the reactions of meta- and para-substituted o-chlorophenolate anions with the same formate esters follow larger values of βnuc = 0.63-0.90 and -β1g = 0.46-0.90. The large values of βnuc and -β1g for the reactions of substituted o-chlorophenolate anions with formate esters may arise from destabilization by the o-chloro group of a stacking interaction that is present in the transition state for reactions of formate esters, but not acetate esters.