56935-60-5

Basic information

• Product Name: 2-CHLORO-N-HYDROXY-BENZAMIDINE
• Synonyms: 2-CHLORO-N-HYDROXY-BENZAMIDINE;Benzenecarboximidamide, 2-chloro-N-hydroxy- (9CI);2-chloro-N-hydroxybenzimidamide;2-Chloro-N-Hydroxy-Benzamidine(WX690161)
• CAS NO: 56935-60-5
• Molecular Formula: C₇H₇ClN₂O
• Molecular Weight: 170.6
• Product Categories: AMIDINE;pharmacetical
• Mol File: 56935-60-5.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 345.4 °C at 760 mmHg
• Flash Point: 162.7 °C
• Appearance: /
• Density: 1.36 g/cm³
• CAS DataBase Reference: 2-CHLORO-N-HYDROXY-BENZAMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-HYDROXY-BENZAMIDINE(56935-60-5)
• EPA Substance Registry System: 2-CHLORO-N-HYDROXY-BENZAMIDINE(56935-60-5)

Safety Data

• Hazardous Substances Data: 56935-60-5(Hazardous Substances Data)

Usage

General Description

2-Chloro-N-hydroxy-benzamidine (CNBA) is a chemical compound with the molecular formula C7H7ClN2O. It is a white to light yellow crystalline solid that is used in the pharmaceutical industry as an intermediate for the synthesis of various organic compounds. CNBA is a potent inhibitor of trypsin and related serine proteases, making it useful in the study of enzyme kinetics and as an antithrombotic agent. It is also used as a reagent in organic synthesis and as a substrate for the preparation of various benzamidine-based drugs. Overall, 2-Chloro-N-hydroxy-benzamidine has a wide range of applications in the pharmaceutical and chemical industries.

Upstream product

• 29568-74-9 2-chloro-N-hydroxybenzimidoyl chloride 
• 873-32-5 2-Chlorobenzonitrile 
• 7664-41-7 ammonia 
• 3717-26-8 2-chlorobenzaldoxime 

Downstream Products

• 16013-08-4 3-(2-chloro-phenyl)-[1,2,4]oxadiazole 
• 261704-60-3 3-(2-chlorophenyl)-5-(phenyl)-1,2,4-oxadiazole 
• 137479-26-6 2-phenyl-4-(2-chlorphenyl)-2,3-dihydro-1,3,5,2-oxadiazaborol 
• 388575-78-8 3-(o-chlorophenyl)-5-(m-nitrophenyl)-1,2,4-oxadiazole 
• 873-32-5 2-Chlorobenzonitrile 
• 609-66-5 2-chlorobenzamide 
• 45765-25-1 (2-chlorophenyl)cyanamide 
• 16672-15-4 3-(2-chlorophenyl)-1,2,4-oxadiazol-5(4H)-one 
• 1597517-07-1 {(S)-2-[3-(2-chlorophenyl)-[1,2,4]oxadiazol-5-yl]pyrrolidin-1-yl}-(5-methyl-2-[1,2,3]triazol-2-ylphenyl)methanone 

Relevant articles and documents

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Efficient synthesis of novel 1-hydroxy-2,4,5-trisubstituted imidazole derivatives via a one-pot, four-component reaction between hydroxylamine, benzonitriles, arylglyoxals and cyclic 1,3-dicarbonyl compounds

A simple, and efficient procedure for the synthesis of novel 2,5-diaryl-1-hydroxy-1H-imidazol-4-yl derivatives via a one-pot, four-component reaction between hydroxylamine, benzonitriles, arylglyoxals and cyclic 1,3-dicarbonyl compounds (Melrum’s acid or dimedone) in ethanol under reflux conditions without using bases and catalysts is reported. All the products were obtained in good yields and their structures were established from their spectroscopic data.

Oxadiazole Derivatives as Dual Orexin Receptor Antagonists: Synthesis, Structure–Activity Relationships, and Sleep-Promoting Properties in Rats

The orexin system plays an important role in the regulation of wakefulness. Suvorexant, a dual orexin receptor antagonist (DORA) is approved for the treatment of primary insomnia. Herein, we outline our optimization efforts toward a novel DORA. We started our investigation with rac-[3-(5-chloro-benzooxazol-2-ylamino)piperidin-1-yl]-(5-methyl-2-[1,2,3]triazol-2-ylphenyl)methanone (3), a structural hybrid of suvorexant and a piperidine-containing DORA. During the optimization, we resolved liabilities such as chemical instability, CYP3A4 inhibition, and low brain penetration potential. Furthermore, structural modification of the piperidine scaffold was essential to improve potency at the orexin 2 receptor. This work led to the identification of (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-{(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl}methanone (51), a potent, brain-penetrating DORA with in vivo efficacy similar to that of suvorexant in rats.