94319-85-4

Basic information

• Product Name: N-(2-aminoethyl)-3-chlorobenzamide
• Synonyms: N-(2-aminoethyl)-3-chlorobenzamide
• CAS NO: 94319-85-4
• Molecular Formula: C₉H₁₁ClN₂O
• Molecular Weight: 198.64944
• Mol File: 94319-85-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 364.7±27.0 °C(Predicted)
• Appearance: /
• Density: 1.226±0.06 g/cm3(Predicted)
• PKA: 13.86±0.46(Predicted)
• CAS DataBase Reference: N-(2-aminoethyl)-3-chlorobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-aminoethyl)-3-chlorobenzamide(94319-85-4)
• EPA Substance Registry System: N-(2-aminoethyl)-3-chlorobenzamide(94319-85-4)

Safety Data

• Hazardous Substances Data: 94319-85-4(Hazardous Substances Data)

Upstream product

• 1644630-64-7 C₁₃H₇Cl₂NO₄ 
• 107-15-3 ethylenediamine 
• 181650-60-2 N-(2-bromoethyl)-3-chlorobenzamide 
• 618-46-2 m-Chlorobenzoyl chloride 
• 77976-05-7 m-Chlorobenzoyl fluoride 
• 18299-54-2 ethylenediamine hydrochloride 

Downstream Products

• 1379000-55-1 C₁₉H₂₆ClN₃O₃ 

Relevant articles and documents

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.

Structure-activity relationships for the binding of arylpiperazines and arylbiguanides at 5-HT3 serotonin receptors

Arylpiperazines are nonselective agents that bind at 5-HT3 serotonin receptors with moderate to high affinity, whereas 1-phenylbiguanide is a low- affinity but more selective 5-HT3 agonist. In an attempt to enhance the affinity of th