32792-59-9

Basic information

• Product Name: 4-Cyanobenzoic acid 4-chlorophenyl ester
• Synonyms: 4-Cyanobenzoic acid 4-chlorophenyl ester
• CAS NO: 32792-59-9
• Molecular Formula: C₁₄H₈ClNO₂
• Molecular Weight: 257.67
• Mol File: 32792-59-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Cyanobenzoic acid 4-chlorophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Cyanobenzoic acid 4-chlorophenyl ester(32792-59-9)
• EPA Substance Registry System: 4-Cyanobenzoic acid 4-chlorophenyl ester(32792-59-9)

Safety Data

• Hazardous Substances Data: 32792-59-9(Hazardous Substances Data)

Upstream product

• 32792-60-2 4-nitrophenyl 4-cyanobenzoate 
• 24573-38-4 4-chlorophenolate 
• 6068-72-0 4-cyanobenzoyl chlorIde 
• 106-48-9 4-chloro-phenol 

Downstream Products

• 24167-50-8 4-cyano-N,N-dimethylbenzamide 

Relevant articles and documents

The effect of acyl substituents on the α-effect: Contrasting α-effect profiles for reactions of 4-nitrophenyl substituted benzoates with neutral and anionic nucleophiles

The magnitude of the α-effect for reactions of 4-nitrophenyl substituted benzoates with a pair of anionic nucleophiles is independent of the electronic nature of the acyl substituent, while the one for the corresponding reactions with a pair of neutral nucleophiles increases as the acyl substituent changes from a strong electron withdrawing substituent to electron donating ones.

Evidence of a stepwise acyl-transfer reaction mechanism: Nonlinear hammett plots for reactions of p-nitrophenyl substituted benzoates with hydroxide and p-chlorophenoxide

The Hammett plots obtained for the title-reactions exhibit a break, i.e. ρ acyl values decrease from 2.21 ~ 2.44 to 1.45 ~ 1.52 as the acyl substituent becomes a strong electron withdrawing group (σ > 0.6). Such a break in the Hammett plots is suggestive of a change in the reaction mechanism and strong evidence of a stepwise mechanism for the acyl-transfer reaction.