610320-57-5

Basic information

• Product Name: Benzamide, 4-chloro-N-[(4-chlorophenyl)methyl]-2-hydroxy-
• CAS NO: 610320-57-5
• Molecular Formula: C14H11Cl2NO2
• Molecular Weight: 296.153
• Mol File: 610320-57-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzamide, 4-chloro-N-[(4-chlorophenyl)methyl]-2-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, 4-chloro-N-[(4-chlorophenyl)methyl]-2-hydroxy-(610320-57-5)
• EPA Substance Registry System: Benzamide, 4-chloro-N-[(4-chlorophenyl)methyl]-2-hydroxy-(610320-57-5)

Safety Data

• Hazardous Substances Data: 610320-57-5(Hazardous Substances Data)

Upstream product

• 5106-98-9 4-chlorosalicylic acid 
• 104-86-9 4-chlorobenzylamine 
• 42365-43-5 (4-chlorophenyl)methanamine hydrochloride 
• 82944-13-6 4-chloro-2-hydroxybenzoyl chloride 

Relevant articles and documents

Structure-activity relationships of N-benzylsalicylamides for inhibition of photosynthetic electron transport

Inhibition of photosynthetic electron transport (PET) in spinach chloroplasts by sixty-one ring-substituted N-benzylsalicylamides was investigated. The inhibitory potency of the compounds expressed by IC50 value varied from 2.0 to 425.3 μmol/L. Several evaluated compounds can be considered as effective PET inhibitors; these include N-(3,4- dichlorobenzyl)-2-hydroxy-5-nitrobenzamide (IC50 = 2.0 μmol/L), 3,5-dibromo-N-(3,4-dichlorobenzyl)-2-hydroxybenzamide (IC50 = 2.3 μmol/L) and 3,5-dibromo-N-(4-chlorobenzyl)-2-hydroxybenzamide (IC50 = 2.6 μmol/L) with activity comparable with that of the standard Diuron (IC50 = 1.9 μmol/L). The PET inhibiting activity increased approximately linearly with increasing lipophilicity of the compounds as well as with the increasing sum of Hammett σ constants of the substituents on the acyl fragment (R1 = H, 5-OCH3, 5-CH3, 5-Cl, 5-Br, 5-NO2, 4-OCH3, 4-Cl, 3,5-Cl and 3,5-Br) and the benzylamide fragment (R2 = H, 4-OCH3, 4-CH3, 4-F, 4-Cl and 3,4-Cl). Based on the evaluated structure-PET inhibiting activity relationships (QSAR) it was confirmed that the inhibitory activity of the compounds depends on lipophilicity (log P or distributive parameters π1 and π2 of individual substituents) and electronic properties of the substituents on the acyl (σ1) and the benzylamide fragments (σ2), the contribution of σ1 being more significant than that of σ2.

On the relationship between the structure and antimycobacterial activity of substituted N-benzylsalicylamides

Sixty-six N-benzylsalicylamides substituted in the acyl moiety in positions 3, 4 or 5 and in position 4 on the benzylic aromatic ring were synthesized. The compounds were tested for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium. To evaluate structure-antimycobacterial activity relationships (QSARs), approaches based on the Free-Wilson as well as a combination of the Free-Wilson and Hansch methods were employed (substituent constants were used to describe the influence of the benzyl substituents, indicator parameters were used for the substituents on the acyl moiety). The use of the Hammett constants for benzyl substituents was not important for QSAR equations. The quadratic representation of lipophilicity parameters (π2) was significant only in QSAR equations of antimycobacterial activity against M. avium.