23564-81-0

Basic information

• Product Name: o-Chloro-N-phenylbenzamidine
• Synonyms: o-Chloro-N-phenylbenzamidine
• CAS NO: 23564-81-0
• Molecular Formula: C₁₃H₁₁ClN₂
• Molecular Weight: 230.69
• Mol File: 23564-81-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: o-Chloro-N-phenylbenzamidine(CAS DataBase Reference)
• NIST Chemistry Reference: o-Chloro-N-phenylbenzamidine(23564-81-0)
• EPA Substance Registry System: o-Chloro-N-phenylbenzamidine(23564-81-0)

Safety Data

• Hazardous Substances Data: 23564-81-0(Hazardous Substances Data)

Upstream product

• 873-32-5 2-Chlorobenzonitrile 
• 4484-20-2 aniline benzenesulfonate 
• 62-53-3 aniline 

Downstream Products

• 99806-12-9 (3aR,9aS)-2-(2-Chloro-phenyl)-4-methyl-1-phenyl-3a,4,9,9a-tetrahydro-1H-imidazo[4,5-b]quinoxaline; hydriodide 
• 132141-38-9 2,N-Dichloro-N'-phenylbenzamidine 
• 832-68-8 6-aminophenanthridine 
• 99806-09-4 (3aR,9aS)-2-(2-Chloro-phenyl)-4-methyl-1-phenyl-3a,4,9,9a-tetrahydro-1H-imidazo[4,5-b]quinoxaline 
• 215233-87-7 N-(3-(1-piperidinyl)-propoxy)-N'-phenyl-benzamidine hydrochloride 
• 3574-96-7 2-(2-chlorophenyl)-1H-benzimidazole 
• 1423125-95-4 2-(2-chlorophenyl)-1,4-diphenyl-1H-imidazole 
• 1283751-33-6 2-(2-chlorophenyl)-4-phenylquinazoline 
• 93-98-1 N-phenyl benzoyl amide 
• 132141-39-0 2-(2'-Chlorophenyl)-1,5-diphenylimidazole 
• 7716-65-6 N-phenylbenzo[d]isothiazol-3-amine 
• 14959-62-7 2-phenyl-3-phenylisoquinolin-1-one 
• 14959-66-1 3-(4-methylphenyl)-2-phenyl-1(2H)-isoquinolone 
• 1448450-25-6 3-(4-fluorophenyl)-2-phenylisoquinolin-1(2H)-one 

Relevant articles and documents

A single step synthesis of 6-aminophenanthridines from anilines and 2-chlorobenzonitriles

Biologically active 6-aminophenanthridines were prepared in a single step procedure: Metal amides in liquid ammonia promoted the condensation of anilines with 2-chloro-benzonitriles. 6-Aminophenanthridines were isolated in moderate yield.

Photoredox synthesis of functionalized quinazolinesviacopper-catalyzed aerobic oxidative Csp2-H annulation of amidines with terminal alkynes

We have developed a visible light-induced photo-redox copper-catalyzed oxidative Csp2-H annulation (Friedel-Crafts-type cyclization) of amidines with terminal alkynes at room temperature to synthesize functionalized quinazolines. We report copp

An eco-friendly approach for the synthesis of 1,2,5-trisubstituted and 4-amino-1,2,5-tetrasubstituted imidazoles via a multi-component condensation

The synthesis of 1,2,5-trisubstituted and 4-amino-1,2,5-tetrasubstituted imidazoles was demonstrated via a two-step cyclo-condensation reaction of aryl amines, carbonitriles, and ethyl bromopyruvate or aryl amines and arylglyoxals in ethanol heated under

Discovery of a Potent and Orally Bioavailable Hypoxia-Inducible Factor 2α (HIF-2α) Agonist and Its Synergistic Therapy with Prolyl Hydroxylase Inhibitors for the Treatment of Renal Anemia

Activation of hypoxia-inducible factor 2 (HIF-2) has emerged as a potent renal anemia treatment strategy. Here, the benzisothiazole derivative 26 was discovered as a novel HIF-2α agonist, which first demonstrated nanomolar activity (EC50 = 490 nM, Emax = 349.2%) in the luciferase reporter gene assay. Molecular dynamics simulations indicated that 26 could allosterically enhance HIF-2 dimerization. Furthermore, compound 26 had a good pharmacokinetic profile (the oral bioavailability in rats was 41.38%) and an in vivo safety profile (the LD50 in mice was greater than 708 mg·kg-1). In the in vivo efficacy assays, the combination of 26 and the prolyl hydroxylase inhibitor, AKB-6548, was confirmed for the first time to synergistically increase the plasma erythropoietin level in mice (from 260 to 2296 pg·mL-1) and alleviate zebrafish anemia induced by doxorubicin. These results provide new insights for HIF-2α agonists and the treatment of renal anemia.

Base-Mediated Amination of Alcohols Using Amidines

Novel and efficient base-mediated N-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands.

Synthesis of 1,2,4,5-tetrasubstituted imidazoles and 2,4,5,6-tetrasubstituted pyrimidines: three-component, the one-pot reaction of arylamidines, malononitrile, and arylglyoxals or aryl aldehydes

A highly efficient one-pot synthesis of the 1,2,4,5-tetrasubstituted imidazoles and 2,4,5,6-tetrasubstituted pyrimidines through an arylamidine, malononitrile, and carbonyl compound by using Et3N in CH3CN at reflux conditions was dev

Nickel-Catalyzed Annulation of o-Haloarylamidines with Aryl Acetylenes: Synthesis of Isoquinolone and 1-Aminoisoquinoline Derivatives

An efficient method for the synthesis of substituted 1(2H)-isoquinolone derivatives via nickel-catalyzed annulation of substituted 2-halobenzamidines with aryl alkynes in the presence of water is described. Benzo[4,5]imidazo[2,1-a]isoquinolines were formed as the dominated products when dry dimethyl sulfoxide was used as the solvent. Furthermore, when benzyl substituted amidines were used as the substrates, debenzylation reaction occured to provide various 1-aminoisoquinoline products. (Figure presented.).

Acid-catalyzed synthesis of imidazole derivatives via N-phenylbenzimidamides and sulfoxonium ylides cyclization

A straightforward method to synthesize imidazole derivatives from amidines and sulfoxonium ylides catalyzed by acids is reported in this study. Specifically, catalyzed by trifluoroacetic acid in DCE solvents can improve synthesis efficiency under metal-fr

Efficient synthesis of 1,2-benzisothiazoles from: O -haloarylamidines and elemental sulfur via N-S/C-S bond formation under transition-metal-free conditions

An efficient method for the synthesis of 1,2-benzisothiazoles from amidines and elemental sulfur via N-S/C-S bond formation under transition-metal-free conditions is described. This reaction is performed smoothly under simple conditions to give the corresponding products in good to high yields with good functional group tolerance.

Vanadium-Catalyzed Oxidative C(CO)-C(CO) Bond Cleavage for C-N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides

A novel vanadium-catalyzed one-pot domino reaction of 1,2-diketones with amidines has been identified that enables their transformation into imides and amides. The reaction proceeds by dual acylation of amidines via oxidative C(CO)-C(CO) bond cleavage of 1,2-diketones to afford N,N′-diaroyl-N-arylbenzamidine intermediates. In the reaction, these intermediates are easily hydrolyzed into imides and amides through vanadium catalysis. This method provides a practical, simple, and mild synthetic approach to access a variety of imides as well as amides in high yields. Moreover, one-step construction of imide and amide bonds with a long-chain alkyl group is an attractive feature of this protocol.