1644630-67-0

Basic information

• Product Name: C₁₅H₁₃ClN₂O₄
• Synonyms: C₁₅H₁₃ClN₂O₄
• CAS NO: 1644630-67-0
• Molecular Weight: 320.732
• Mol File: 1644630-67-0.mol

Chemical Properties

• CAS DataBase Reference: C₁₅H₁₃ClN₂O₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₅H₁₃ClN₂O₄(1644630-67-0)
• EPA Substance Registry System: C₁₅H₁₃ClN₂O₄(1644630-67-0)

Safety Data

• Hazardous Substances Data: 1644630-67-0(Hazardous Substances Data)

Upstream product

• 4755-50-4 4-(dimethylamino)benzoyl chloride 
• 89-64-5 p-chloro-o-nitrophenol 

Downstream Products

• 207864-27-5 (4-Dimethylamino-benzoylamino)-acetic acid ethyl ester 
• 19353-92-5 4-(dimethylamino)benzohydrazide 
• 1156667-34-3 C₁₃H₁₇N₃O₄ 
• 108191-13-5 N-benzyl-[4-(N,N-dimethylamino)]-benzamide 
• 96603-18-8 4-(dimethylamino)-N-(2-hydroxyethyl)benzamide 

Relevant articles and documents

Kinetic study on aminolysis of 4-chloro-2-nitrophenyl X-substituted-benzoates in Acetonitrile and in 80 mol % H2O/20 mol % DMSO: Effect of medium on reactivity and reaction mechanism

A kinetic study on aminolysis of 4-chloro-2-nitrophenyl X-substituted-benzoates (6a-i) in MeCN is reported. The Hammett plot for the reactions of 6a-i with piperidine consists of two intersecting straight lines, while the Yukawa-Tsuno plot exhibits an exc

The α-effect in hydrazinolysis of 4-chloro-2-nitrophenyl x-substituted-benzoates: Effect of substituent x on reaction mechanism and the α-effect

Second-order rate constants (kN) have been measured spectrophotometrically for the reaction of 4-chloro-2- nitrophenyl X-substituted-benzoates (6a-6h) with a series of primary amines including hydrazine in 80 mol % H2O/20 mol % DMSO at 25.0°C. The Bronsted-type plot for the reaction of 4-chloro-2-nitrophenyl benzoate (6d) is linear with βnuc = 0.74 when hydrazine is excluded from the correlation. Such a linear Bronsted-type plot is typical for reactions reported previously to proceed through a stepwise mechanism in which expulsion of the leaving group occurs in the rate-determining step (RDS). The Hammett plots for the reactions of 6a-6h with hydrazine and glycylglycine are nonlinear. In contrast, the Yukawa-Tsuno plots exhibit excellent linear correlations with ?X = 1.29-1.45 and r = 0.53-0.56, indicating that the nonlinear Hammett plots are not due to a change in RDS but are caused by resonance stabilization of the substrates possessing an electron-donating group (EDG). Hydrazine is ca. 47-93 times more reactive than similarly basic glycylglycine toward 6a-6h (e.g., the α-effect). The α-effect increases as the substituent X in the benzoyl moiety becomes a stronger electronwithdrawing group (EWG), indicating that destabilization of the ground state (GS) of hydrazine through the repulsion between the nonbonding electron pairs on the two N atoms is not solely responsible for the substituent-dependent α-effect. Stabilization of transition state (TS) through five-membered cyclic TSs, which would increase the electrophilicity of the reaction center or the nucleofugality of the leaving group, contributes to the α-effect observed in this study.